pmedpharmФармация и фармакологияPharmacy & Pharmacology2307-92662413-2241Pyatigorsk Medical and Pharmaceutical Institute - branch of Volgograd State Medical Univer10.19163/2307-9266-2025-13-6-500-514pmedpharm-1763Research ArticleОРИГИНАЛЬНАЯ СТАТЬЯRESEARCH ARTICLEСинтез и мультимодальная активность 3a,6-эпоксиизоиндоло-2(3H)-(карбокс/тио/селен)амидов в моделях реакции гликирования, окислительного стресса и воспаления, ориентация на разработку средств, воздействующих на триггерные механизмы фиброзированияSynthesis and multimodal activity of 3a,6-epoxyisoindole-2(3H)-(carbox/thio/seleno)amides in models of glycation, oxidative stress, and inflammation: Toward the development of agents targeting the triggering mechanisms of fibrogenesishttps://orcid.org/0000-0001-9141-4417ИбрагимоваУ. М.IbragimovaU. M.

ассистент кафедры фармакологии и биоинформатики ФГБОУ ВО ВолгГМУ Минздрава России. 

Россия, 400066, г. Волгоград, пл. Павших Борцов, д. 1.

 

assistant Professor of the Department of Pharmacology and Bioinformatics of the Volgograd State Medical University.

1 Pavshikh Bortsov Sq., Volgograd, Russia, 400066.

iumida888@gmail.comhttps://orcid.org/0009-0000-8539-6590ВалуйскийН. В.ValuyskyN. V.

лаборант-исследователь лаборатории метаботропных лекарственных средств ФГБОУ ВО ВолгГМУ Минздрава России.

Россия, 400066, г. Волгоград, пл. Павших Борцов, д. 1.

laboratory assistant of the Laboratory of Metabotropic Medicines, Volgograd State Medical University.

1 Pavshikh Bortsov Sq., Volgograd, Russia, 400066.

AjI024FiB@gmail.comhttps://orcid.org/0009-0002-8217-8381РайбергВ. Р.RaybergV. R.

лаборант-исследователь лаборатории метаботропных лекарственных средств ФГБОУ ВО ВолгГМУ Минздрава России. 

Россия, 400066, г. Волгоград, пл. Павших Борцов, д. 1.

laboratory assistant at the Laboratory of Metabotropic Medicines, Volgograd State Medical University.

1 Pavshikh Bortsov Sq., Volgograd, Russia, 400066.

vita.raiberg@gmail.comhttps://orcid.org/0009-0000-3110-0213СорокинаС. А.SorokinaS. A.

лаборант-исследователь лаборатории метаботропных лекарственных средств ФГБОУ ВО ВолгГМУ Минздрава России. 

Россия, 400066, г. Волгоград, пл. Павших Борцов, д. 1

laboratory assistant of the Laboratory of Metabotropic Medicines, Volgograd State Medical University.

1 Pavshikh Bortsov Sq., Volgograd, Russia, 400066.

sveta.sorokina182839@gmail.comhttps://orcid.org/0009-0006-7454-8337ЖуковаК. И.ZhukovaK. I.

лаборант-исследователь лаборатории метаботропных лекарственных средств ФГБОУ ВО ВолгГМУ Минздрава России. 

Россия, 400066, г. Волгоград, пл. Павших Борцов, д. 1.

 

laboratory assistant at the Laboratory of Metabotropic Medicines, Volgograd State Medical University.

1 Pavshikh Bortsov Sq., Volgograd, Russia, 400066.

zhukovaksenia11@gmail.comhttps://orcid.org/0009-0008-8427-0222ДерягинД. К.DeryaginD. K.

студент 4 курса лечебного факультета ФГБОУ ВО ВолгГМУ Минздрава России. 

Россия, 400066, г. Волгоград, пл. Павших Борцов, д. 1.

4th year student of the Medical Faculty, Volgograd State Medical University. 

1 Pavshikh Bortsov Sq., Volgograd, Russia, 400066.

denis_deryagin777@mail.ruhttps://orcid.org/0009-0005-7613-4317УхоренкоИ. С.UkhorenkoI. S.

студент 3 курса лечебного факультета ФГБОУ ВО ВолгГМУ Минздрава России. 

Россия, 400066, г. Волгоград, пл. Павших Борцов, д. 1.

3rd year student of the Medical Faculty, Volgograd State Medical University. 

1 Pavshikh Bortsov Sq., Volgograd, Russia, 400066.

Uxorenko@gmail.comhttps://orcid.org/0009-0001-9297-5379ГригорьеваА. А.GrigoryevaA. A.

бакалавр 4 года обучения кафедры органической химии РУДН. 

Россия, 117198, г. Москва, ул. Миклухо-Маклая, д. 6.

Bachelor of the 4th year of the Department of Organic Chemistry, RUDN University. 

6 Miklukho-Maklaya Str., Moscow, Russia, 117198.

elenaaa448@gmail.comhttps://orcid.org/0009-0000-9485-6341ЩевниковД. М.ShchevnikovD. M.

аспирант 2 года обучения кафедры органической химии РУДН. 

Россия, 117198, г. Москва, ул. Миклухо-Маклая, д. 6.

2nd year graduate student of the Department of Organic Chemistry of the RUDN University. 

6 Miklukho-Maklaya Str., Moscow, Russia, 117198.

shchevnikov.dm@gmail.comhttps://orcid.org/0000-0001-9175-7583ЗайцевВ. П.ZaytsevV. P.

кандидат химических наук, доцент кафедры органической химии РУДН. 

Россия, 117198, г. Москва, ул. Миклухо-Маклая, д. 6.

Candidate of Sciences (Chemistry), Assistant Professor of the Department of Organic Chemistry, RUDN University. 

6 Miklukho-Maklaya Str., Moscow, Russia, 117198.

zaytsev-vp@rudn.ruhttps://orcid.org/0000-0002-0162-0653ЛитвиновР. А.LitvinovR. A.

кандидат медицинских наук, старший научный сотрудник лаборатории метаботропных лекарственных средств ФГБОУ ВО ВолгГМУ Минздрава России; генеральный директор ООО «ИнноВВита». 

Россия, 400066, г. Волгоград, пл. Павших Борцов, д. 1.

Россия, 400066, г. Волгоград, ул. Комсомольская, д. 6, оф. 401, комн. 2.

Candidate of Sciences (Medicine), Senior Researcher of the Laboratory of Metabotropic Medicines, Volgograd State Medical University; General Director of InnoVVita LLC. 

1 Pavshikh Bortsov Sq., Volgograd, Russia, 400066.

6 Komsomolskaya Str., office 401, room 2, Volgograd, Russia, 400066. 

litvinov_r@innovvita.comФедеральное государственное бюджетное образовательное учреждение высшего образования «Волгоградский государственный медицинский университет» Министерства здравоохранения Российской Федерации.РоссияVolgograd State Medical University.Russian FederationФедеральное государственное бюджетное образовательное учреждение высшего образования «Волгоградский государственный медицинский университет» Министерства здравоохранения Российской ФедерацииРоссияVolgograd State Medical University.Russian FederationФедеральное государственное автономное образовательное учреждение высшего образования «Российский университет дружбы народов имени Патриса Лумумбы».РоссияPeoples’ Friendship University of Russia (RUDN University).Russian FederationФедеральное государственное автономное образовательное учреждение высшего образования «Российский университет дружбы народов имени Патриса Лумумбы»РоссияPeoples’ Friendship University of Russia (RUDN University).Russian Federation1. Федеральное государственное бюджетное образовательное учреждение высшего образования «Волгоградский государственный медицинский университет» Министерства здравоохранения Российской Федерации. 2. Общество с ограниченной ответственностью «ИННОВВИТА».Россия1. Volgograd State Medical University. 2. InnoVVita LLC.Russian Federation202529112025136500514Copyright © Ибрагимова У.М., Валуйский Н.В., Райберг В.Р., Сорокина С.А., Жукова К.И., Дерягин Д.К., Ухоренко И.С., Григорьева А.А., Щевников Д.М., Зайцев В.П., Литвинов Р.А., 20252025Ибрагимова У.М., Валуйский Н.В., Райберг В.Р., Сорокина С.А., Жукова К.И., Дерягин Д.К., Ухоренко И.С., Григорьева А.А., Щевников Д.М., Зайцев В.П., Литвинов Р.А.Ibragimova U.M., Valuysky N.V., Rayberg V.R., Sorokina S.A., Zhukova K.I., Deryagin D.K., Ukhorenko I.S., Grigoryeva A.A., Shchevnikov D.M., Zaytsev V.P., Litvinov R.A.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://www.pharmpharm.ru/jour/article/view/1763Цель

Цель. В ряду 3a,6-эпоксиизоиндол-2(3H)-(карбокс/тио/селен)амидов выявить мультимодальный скаффолд, пригодный в качестве основы для дальнейшей разработки средств профилактики и терапии фиброзных заболеваний; оценить антигликирующую и антиоксидантную активность ряда соединений, отобрать нецитотоксичное соединение-лидер со сбалансированным сочетанием двух активностей и предварительно проверить его противовоспалительное действие.

Материалы и методы

Материалы и методы. Целевые 3a,6-эпоксиизоиндол-2(3H)-(карбокс/тио/селен)амиды синтезированы с использованием IMDAF-реакции. Антигликирующую активность оценивали в модели гликирования альбумина глюкозой, регистрируя флуоресценцию конечных продуктов гликирования (КПГ). Антиоксидантные свойства определяли с применением ABTS. Цитотоксическое и противовоспалительное действие изучали на перитонеальных макрофагах белых половозрелых мышей дикого типа (n=4, масса 30–35 г). Цитотоксичность оценивали с использованием МТТ-теста и по высвобождению лактатдегидрогеназы (ЛДГ), противовоспалительный эффект — в модели ЛПС-индуцированной продукции оксида азота (NO).

Результаты

Результаты. В результате работы показаны перспективные направления модификации эпоксиизоиндольного скаффолда для разработки новых лекарственных препаратов; предложена система поиска средств для профилактики и лечения патологий, зависимых от пусковых механизмов повреждения гликированием и окислительным стрессом, в том числе фиброзных болезней. Идентифицированы активные молекулы (производные гидрированного 3a,6-эпокиизоиндола). Соединение 2.10, а именно 7a-хлор-N-(4-хлорфенил)-1,6,7,7a-тетрагидро3a,6-эпокиизоиндол-2(3H)-карботиоамид, продемонстрировало оптимальное сочетание антигликирующей (в концентрации 100 мкМ ингибирование реакции гликирования на 40,1±1,7%) и антиоксидантной активности (в концентрации 111 мкМ снижение интенсивности окраски ABTS•+ на 57,1±1,1%) при низкой цитотоксичности (проявляется в концентрациях ≥250 мкМ), тогда как 2.16–2.19 (содержат структурный N-ароильный фрагмент) отличались исключительно высокой антиоксидантной активностью (снижение интенсивности окраски ABTS•+ на 95,0–96,5%) без согласования таковой с антигликирующим действием (для лучшего соединения не достигает 15% ингибирования реакции гликирования). Противовоспалительная активность 2.10 в использованной модели выявлена не была.

Заключение

Заключение. Соединение 2.10 — перспективная основа для дальнейшей оптимизации структуры в направлении создания средств, ориентированных на ранние звенья патогенеза заболеваний, зависимых от механизмов повреждения гликированием и окислительным стрессом, в том числе для профилактики и лечения фиброзного ремоделирования.

The aim

The aim. Within a series of 3a,6-epoxyisoindole-2(3H)-(carbox/thio/seleno)amides, we sought to identify a multimodal scaffold suitable for the further development of agents to prevent and treat fibrotic diseases by assessing of compound’s ability to mitigate glycation and oxidative stress, key triggers of fibrogenesis; to select a non-cytotoxic lead with a balanced combination of these two activities, and to preliminarily evaluate its anti-inflammatory potential.

Materials and methods

Materials and methods. Target 3a,6-epoxyisoindole-2(3H)-(carbox/thio/seleno)amides were synthesised using the IMDAF approach. Antiglycation activity was evaluated in a bovine serum albumin-glucose model by registering advanced glycation end-product (AGE) fluorescence. Antioxidant properties were determined using the ABTS assay. Cytotoxicity and antiinflammatory effects were studied in peritoneal macrophages from adult wild-type white mice (n = 4; body mass 30–35 g). Cytotoxicity was assessed by the MTT assay and lactate dehydrogenase (LDH) release, while anti-inflammatory effects were evaluated in a model of LPS-induced nitric oxide (NO) production.

Results

Results. The study delineates promising directions for modifying the epoxyisoindole scaffold for drug discovery and proposes a screening framework for agents targeting pathologies dependent on non-enzymatic damaging mechanisms (glycation, oxidation), including fibrotic diseases. Active molecules were identified among derivatives of hydrogenated 3a,6-epoxyisoindole. Compound 2.10 — 7a-chloro-N-(4-chlorophenyl)-1,6,7,7a-tetrahydro-3a,6-epoxyisoindole-2(3H)carbothioamide — exhibited an optimal balance of antiglycation (at 100 μM, inhibition of glycation 40.1 ± 1.7%) and antioxidant activity (at 111 μM, reduction in ABTS•+ colour intensity 57.1 ± 1.1%) with low cytotoxicity (apparent from ≥ 250 μM). By contrast, compounds 2.16–2.19 (bearing an aroyl fragment) showed exceptionally high antioxidant activity (95.0–96.5% reduction in ABTS•+ colour intensity) without concordant antiglycation effects (inhibition not exceeding 15%). In the model used, anti-inflammatory activity of 2.10 was not detected.

Conclusion

Conclusion. Compound 2.10 is a promising starting point for further structural optimisation toward agents acting on early pathogenetic events driven by non-enzymatic damaging triggers, including the prevention and treatment of fibrotic remodelling.

эпоксиизоиндолантигликированиеантиоксидантная активностьвоспалениефиброзмакрофагиepoxyisoindoleantiglycationantioxidant activityinflammationfibrosismacrophagesИсследование выполнено за счет средств гранта Российского научного фонда и Администрации Волгоградской области № 24-24-20112 (https://rscf.ru/project/24-24-20112/).The study was carried out at the expense of the grant funds of the Russian Science Foundation and the Administration of the Volgograd Region No. 24-24-20112 (https://rscf.ru/project/24-24-20112/).ReferencesBasak T., Saraswati S. Editorial: Fibrotic tissue remodeling as a driver of disease pathogenesis // Front Mol Biosci. – 2023. – Vol. 10. – P. 1278388. DOI: 10.3389/fmolb.2023.1278388Basak T, Saraswati S. Editorial: Fibrotic tissue remodeling as a driver of disease pathogenesis. Front Mol Biosci. 2023;10:1278388. DOI: 10.3389/fmolb.2023.1278388Younesi F.S., Miller A.E., Barker T.H., Rossi F.M.V., Hinz B. Fibroblast and myofibroblast activation in normal tissue repair and fibrosis // Nat Rev Mol Cell Biol. – 2024. – Vol. 25, No. 8. – P. 617–638. DOI: 10.1038/s41580-024-00716-0. Erratum in: Nat Rev Mol Cell Biol. – 2024. – Vol. 25, No. 8. – P. 671. DOI: 10.1038/s41580-024-00744-wYounesi FS, Miller AE, Barker TH, Rossi FMV, Hinz B. Fibroblast and myofibroblast activation in normal tissue repair and fibrosis. Nat Rev Mol Cell Biol. 2024;25(8):617–638. DOI: 10.1038/s41580-024-00716-0. Erratum in: Nat Rev Mol Cell Biol. 2024;25(8):671. DOI: 10.1038/s41580-024-00744-wMack M. Inflammation and fibrosis // Matrix Biol. – 2018. – Vol. 68-69. – P. 106–121. DOI: 10.1016/j.matbio.2017.11.010Mack M. Inflammation and fibrosis. Matrix Biol. 2018;68-69:106–121. DOI: 10.1016/j.matbio.2017.11.010Hao H., Li X., Li Q., Lin H., Chen Z., Xie J., Xuan W., Liao W., Bin J., Huang X., Kitakaze M., Liao Y. FGF23 promotes myocardial fibrosis in mice through activation of β-catenin // Oncotarget. – 2016. – Vol. 7, No. 40. – P. 64649–64664. DOI: 10.18632/oncotarget.11623Hao H, Li X, Li Q, Lin H, Chen Z, Xie J, Xuan W, Liao W, Bin J, Huang X, Kitakaze M, Liao Y. FGF23 promotes myocardial fibrosis in mice through activation of β-catenin. Oncotarget. 2016;7(40):64649–64664. DOI: 10.18632/oncotarget.11623Li Y., Zhao J., Yin Y., Li K., Zhang C., Zheng Y. The Role of IL-6 in Fibrotic Diseases: Molecular and Cellular Mechanisms // Int J Biol Sci. – 2022. – Vol. 18, No. 14. – P. 5405–5414. DOI: 10.7150/ijbs.75876Li Y, Zhao J, Yin Y, Li K, Zhang C, Zheng Y. The Role of IL-6 in Fibrotic Diseases: Molecular and Cellular Mechanisms. Int J Biol Sci. 2022;18(14):5405–5414. DOI: 10.7150/ijbs.75876O’Reilly S. Interleukin-11 and its eminent role in tissue fibrosis: a possible therapeutic target // Clin Exp Immunol. – 2023. – Vol. 214, No. 2. – P. 154–161. DOI: 10.1093/cei/uxad108O'Reilly S. Interleukin-11 and its eminent role in tissue fibrosis: a possible therapeutic target. Clin Exp Immunol. 2023;214(2):154–161. DOI: 10.1093/cei/uxad108Mayorca-Guiliani A.E., Leeming D.J., Henriksen K., Mortensen J.H., Nielsen S.H., Anstee Q.M., Sanyal A.J., Karsdal M.A., Schuppan D. ECM formation and degradation during fibrosis, repair, and regeneration // NPJ Metab Health Dis. – 2025. – Vol. 3, No. 1. – P. 25. DOI: 10.1038/s44324-025-00063-4Mayorca-Guiliani AE, Leeming DJ, Henriksen K, Mortensen JH, Nielsen SH, Anstee QM, Sanyal AJ, Karsdal MA, Schuppan D. ECM formation and degradation during fibrosis, repair, and regeneration. NPJ Metab Health Dis. 2025;3(1):25. DOI: 10.1038/s44324-025-00063-4Roh J.S., Sohn D.H. Damage-Associated Molecular Patterns in Inflammatory Diseases // Immune Netw. – 2018. – Vol. 18, No. 4. – P. e27. DOI: 10.4110/in.2018.18.e27Roh JS, Sohn DH. Damage-Associated Molecular Patterns in Inflammatory Diseases. Immune Netw. 2018;18(4):e27. DOI: 10.4110/in.2018.18.e27Otoupalova E., Smith S., Cheng G., Thannickal V.J. Oxidative Stress in Pulmonary Fibrosis // Compr Physiol. – 2020. – Vol. 10, No. 2. – P. 509–547. DOI: 10.1002/cphy.c190017Otoupalova E, Smith S, Cheng G, Thannickal VJ. Oxidative Stress in Pulmonary Fibrosis. Compr Physiol. 2020;10(2):509–547. DOI: 10.1002/cphy.c190017Zhao J., Randive R., Stewart J.A. Molecular mechanisms of AGE/RAGE-mediated fibrosis in the diabetic heart // World J Diabetes. – 2014. – Vol. 5, No. 6. – P. 860–867. DOI: 10.4239/wjd.v5.i6.860Zhao J, Randive R, Stewart JA. Molecular mechanisms of AGE/RAGE-mediated fibrosis in the diabetic heart. World J Diabetes. 2014;5(6):860–7. DOI: 10.4239/wjd.v5.i6.860De Vriese A.S., Flyvbjerg A., Mortier S., Tilton R.G., Lameire N.H. Inhibition of the interaction of AGE-RAGE prevents hyperglycemia-induced fibrosis of the peritoneal membrane // J Am Soc Nephrol. – 2003. – Vol. 14, No. 8. – P. 2109–2118. DOI: 10.1681/ASN.V1482109De Vriese AS, Flyvbjerg A, Mortier S, Tilton RG, Lameire NH. Inhibition of the interaction of AGE-RAGE prevents hyperglycemia-induced fibrosis of the peritoneal membrane. J Am Soc Nephrol. 2003;14(8):2109–2118. DOI: 10.1681/ASN.V1482109Li L., Li Q., Wei L., Wang Z., Ma W., Liu F., Shen Y., Zhang S., Zhang X., Li H., Qian Y. Dexamethasone combined with berberine is an effective therapy for bleomycin-induced pulmonary fibrosis in rats // Exp Ther Med. – 2019. – Vol. 18, No. 4. – P. 2385–2392. DOI: 10.3892/etm.2019.7861Li L, Li Q, Wei L, Wang Z, Ma W, Liu F, Shen Y, Zhang S, Zhang X, Li H, Qian Y. Dexamethasone combined with berberine is an effective therapy for bleomycin-induced pulmonary fibrosis in rats. Exp Ther Med. 2019;18(4):2385–2392. DOI: 10.3892/etm.2019.7861Gulbrandsen H.S., Serigstad H., Read M.L., Joos I., Gundersen L.L. Formation of 8-Hydroxyphenanthridines by Microwave-Mediated IMDAF Reactions. – Vol. Synthesis Directed towards Lycorine Alkaloids // Eur J Org Chem. – 2019. – Vol. – 2019, No. 35. – P. 6044–6052. DOI: 10.1002/ejoc.201901000Gulbrandsen HS, Serigstad H, Read ML, Joos I, Gundersen LL. Formation of 8-Hydroxyphenanthridines by Microwave-Mediated IMDAF Reactions; Synthesis Directed towards Lycorine Alkaloids. Eur J Org Chem. 2019;2019(35):6044–6052. DOI: 10.1002/ejoc.201901000Read M.L., Krapp A., Miranda P.O., Gundersen L.L. Synthesis of complex fused polycyclic heterocycles utilizing IMDAF reactions of allylamino- or allyloxy-furyl(hetero)arenes // Tetrahedron. – 2012. – Vol. 68. – p. 1869–1885. DOI: 10.1016/j.tet.2011.12.079Read ML, Krapp A, Miranda PO, Gundersen LL. Synthesis of complex fused polycyclic heterocycles utilizing IMDAF reactions of allylamino- or allyloxy-furyl(hetero)arenes. Tetrahedron. 2012;68:1869–1885. DOI: 10.1016/j.tet.2011.12.079Zubkov F.I., Ershova J.D., Zaytsev V.P., Obushak M.D., Matiychuk V.S., Sokolova E.A., Khrustalev V.N., Varlamov A.V. The first example of an intramolecular Diels–Alder furan (IMDAF) reaction of iminium salts and its application in a short and simple synthesis of the isoindolo[1,2-a]isoquinoline core of the jamtine and hirsutine alkaloids // Tetrahedron Lett. – 2010. – Vol. 51. – Р. 6822–6824. DOI: 10.1016/j.tetlet.2010.10.046Zubkov FI, Ershova JD, Zaytsev VP, Obushak MD, Matiychuk VS, Sokolova EA, Khrustalev VN, Varlamov AV. The first example of an intramolecular Diels–Alder furan (IMDAF) reaction of iminium salts and its application in a short and simple synthesis of the isoindolo[1,2-a]isoquinoline core of the jamtine and hirsutine alkaloids. Tetrahedron Lett. 2010;51:6822–6824. DOI: 10.1016/j.tetlet.2010.10.046Zubkov F.I., Ershova J.D., Orlova A.A., Zaytsev V.P., Nikitina E.V., Peregudov A.S., Gurbanov A.V., Borisov R.S., Khrustalev V.N., Maharramov A.M., Varlamov A.V. A new approach to construction of isoindolo[1,2-a]isoquinoline alkaloids Nuevamine, Jamtine, and Hirsutine via IMDAF reaction // Tetrahedron. – 2009. – Vol. 65. – P. 3789–3803. DOI: 10.1016/j.tet.2009.02.024Zubkov FI, Ershova JD, Orlova AA, Zaytsev VP, Nikitina EV, Peregudov AS, Gurbanov AV, Borisov RS, Khrustalev VN, Maharramov AM, Varlamov AV. A new approach to construction of isoindolo[1,2-a]isoquinoline alkaloids Nuevamine, Jamtine, and Hirsutine via IMDAF reaction. Tetrahedron. 2009;65:3789–3803. DOI: 10.1016/j.tet.2009.02.024Zubkov F.I., Nikitina E.V., Galeev T.R., Zaytsev V.P., Khrustalev V.N., Novikov R.A., Orlova D.N., Varlamov A.V. General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations // Tetrahedron. – 2014. – Vol. 70. – P. 1659–1690. DOI: 10.1016/j.tet.2014.01.008Zubkov FI, Nikitina EV, Galeev TR, Zaytsev VP, Khrustalev VN, Novikov RA, Orlova DN, Varlamov AV. General synthetic approach towards annelated 3a,6-epoxyisoindoles by tandem acylation/IMDAF reaction of furylazaheterocycles. Scope and limitations. Tetrahedron. 2014;70:1659–1690. DOI: 10.1016/j.tet.2014.01.008Nadirova M.A., Khanova A.V., Zubkov F.I., Mertsalov D.F., Kolesnik I.A., Petkevich S.K., Potkin V.I., Shetnev A.A., Presnukhina S.I., Sinelshchikova A.A., Grigoriev M.S., Zaytsev V.P. Cascade of the Hinsberg/IMDAF reactions in the synthesis of 2-arylsulfonyl-3a,6-epoxyisoindoles and 4a,7-epoxyisoquinolines in water // Tetrahedron. – 2021. – Vol. 85. – P. 132032. DOI: 10.1016/j.tet.2021.132032Nadirova MA, Khanova AV, Zubkov FI, Mertsalov DF, Kolesnik IA, Petkevich SK, Potkin VI, Shetnev AA, Presnukhina SI, Sinelshchikova AA, Grigoriev MS, Zaytsev VP. Cascade of the Hinsberg/IMDAF reactions in the synthesis of 2-arylsulfonyl-3a,6-epoxyisoindoles and 4a,7-epoxyisoquinolines in water. Tetrahedron. 2021;85:132032. DOI: 10.1016/j.tet.2021.132032Zubkov F.I., Mertsalov D.F., Zaytsev V.P., Varlamov A.V., Gurbanov A.V., Dorovatovskii P.V., Timofeeva T.V., Khrustalev V.N., Mahmudov K.T. Halogen bonding in Wagner–Meerwein rearrangement products // J Mol Liq. – 2018. – Vol. 249. – P. 949–952. DOI: 10.1016/j.molliq.2017.11.116Zubkov FI, Mertsalov DF, Zaytsev VP, Varlamov AV, Gurbanov AV, Dorovatovskii PV, Timofeeva TV, Khrustalev VN, Mahmudov KT. Halogen bonding in Wagner–Meerwein rearrangement products. J Mol Liq. 2018;249:949–952. DOI: 10.1016/j.molliq.2017.11.116Trastulli Colangeli S., Campana F., Ferlin F., Vaccaro L. A waste-minimized protocol for electrochemical reductive amination and its environmental assessment // Green Chem. – 2024. – Vol. 27. – P. 633–641. DOI: 10.1039/d4gc04847dTrastulli Colangeli S, Campana F, Ferlin F, Vaccaro L. A waste-minimized protocol for electrochemical reductive amination and its environmental assessment. Green Chem. 2024;27:633–641. DOI: 10.1039/d4gc04847dMüller C., Diehl V., Lichtenthaler F.W. Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose // Tetrahedron. – 1998. – Vol. 54. – P. 10703–10712. DOI: 10.1016/S0040-4020(98)00634-6Müller C, Diehl V, Lichtenthaler FW. Building blocks from sugars. Part 23. Hydrophilic 3-pyridinols from fructose and isomaltulose. Tetrahedron. 1998;54:10703–10712. DOI: 10.1016/S0040-4020(98)00634-6Deng J., Mo L.P., Zhao F.Y., Hou L.L., Yang L., Zhang Z.H. Sulfonic acid supported on hydroxyapatite-encapsulated γ- Fe2O3 nanocrystallites as a magnetically separable catalyst for one-pot reductive amination of carbonyl compounds // Green Chem. – 2011. – Vol. 13. – P. 2576–2584. DOI: 10.1039/C1GC15470BDeng J, Mo LP, Zhao FY, Hou LL, Yang L, Zhang ZH. Sulfonic acid supported on hydroxyapatite-encapsulated γ- Fe2O3 nanocrystallites as a magnetically separable catalyst for one-pot reductive amination of carbonyl compounds. Green Chem. 2011;13:2576–2584. DOI: 10.1039/C1GC15470BSaberi D., Akbari J., Mahdudi S., Heydari A. Reductive amination of aldehydes and ketones catalyzed by deep eutectic solvent using sodium borohydride as a reducing agent // J Mol Liq. – 2014. – Vol. 196. – P. 208–210. DOI: 10.1016/j.molliq.2014.03.024Saberi D, Akbari J, Mahdudi S, Heydari A. Reductive amination of aldehydes and ketones catalyzed by deep eutectic solvent using sodium borohydride as a reducing agent. J Mol Liq. 2014;196:208–210. DOI: 10.1016/j.molliq.2014.03.024Mertsalov D.F., Shchevnikov D.M., Lovtsevich L.V., Novikov R.A., Khrustalev V.N., Grigoriev M.S., Romanycheva A.A., Shetnev A.A., Bychkova O.P., Trenin A.S., Zaytsev V.P. The short route to chalcogenurea-substituted 3a,6-epoxyisoindoles via an intramolecular Diels–Alder furan (IMDAF) reaction. Antibacterial and antifungal activity // New J Chem. – 2024. – Vol. 48. – P. 12947–12959. DOI: 10.1039/d4nj01174kMertsalov DF, Shchevnikov DM, Lovtsevich LV, Novikov RA, Khrustalev VN, Grigoriev MS, Romanycheva AA, Shetnev AA, Bychkova OP, Trenin AS, Zaytsev VP. The short route to chalcogenurea-substituted 3a,6-epoxyisoindoles via an intramolecular Diels–Alder furan (IMDAF) reaction. Antibacterial and antifungal activity. New J Chem. 2024;48:12947–12959. DOI: 10.1039/d4nj01174kMertsalov D.F., Lovtsevich L.V., Shchevnikov D.M., Dobrushina Yu.M., Sorokina E.A., Grigoriev M.S., Zaytsev V.P. An intramolecular Diels–Alder reaction in the synthesis of N-aroyl-3a,6-epoxyisoindole-2-carbothioamides // Chem Heterocycl Compd. – 2024. – Vol. 60. – P. 512–523. DOI: 10.1007/s10593-024-03369-1Mertsalov DF, Lovtsevich LV, Shchevnikov DM, Dobrushina YuM, Sorokina EA, Grigoriev MS, Zaytsev VP. An intramolecular Diels–Alder reaction in the synthesis of N-aroyl-3a,6-epoxyisoindole-2-carbothioamides. Chem Heterocycl Compd. 2024;60:512–523. DOI: 10.1007/s10593-024-03369-1Whiteman M., Li L., Rose P., Tan C.H., Parkinson D.B., Moore P.K. The effect of hydrogen sulfide donors on lipopolysaccharide-induced formation of inflammatory mediators in macrophages // Antioxid Redox Signal. – 2010. – Vol. 12, No. 10. – P. 1147–1154. DOI: 10.1089/ars.2009.2899Whiteman M, Li L, Rose P, Tan CH, Parkinson DB, Moore PK. The effect of hydrogen sulfide donors on lipopolysaccharide-induced formation of inflammatory mediators in macrophages. Antioxid Redox Signal. 2010;12(10):1147–54. DOI: 10.1089/ars.2009.2899Fathy M., Fawzy M.A., Hintzsche H., Nikaido T., Dandekar T., Othman E.M. Eugenol Exerts Apoptotic Effect and Modulates the Sensitivity of HeLa Cells to Cisplatin and Radiation // Molecules. – 2019. – Vol. 24, No. 21. – P. 3979. DOI: 10.3390/molecules24213979Fathy M, Fawzy MA, Hintzsche H, Nikaido T, Dandekar T, Othman EM. Eugenol Exerts Apoptotic Effect and Modulates the Sensitivity of HeLa Cells to Cisplatin and Radiation. Molecules. 2019;24(21):3979. DOI: 10.3390/molecules24213979El-Demerdash E. Anti-inflammatory and antifibrotic effects of methyl palmitate // Toxicol Appl Pharmacol. – 2011. – Vol. 254, No. 3. – P. 238–244. DOI: 10.1016/j.taap.2011.04.016El-Demerdash E. Anti-inflammatory and antifibrotic effects of methyl palmitate. Toxicol Appl Pharmacol. 2011;254(3):238–44. DOI: 10.1016/j.taap.2011.04.016Plumb J.A., Milroy R., Kaye S.B. Effects of the pH dependence of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide-formazan absorption on chemosensitivity determined by a novel tetrazolium-based assay // Cancer Res. – 1989. – Vol. 49, No. 16. – P. 4435–4440.Plumb JA, Milroy R, Kaye SB. Effects of the pH dependence of 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-tetrazolium bromide-formazan absorption on chemosensitivity determined by a novel tetrazolium-based assay. Cancer Res. 1989;49(16):4435–4440.McComb R.B., Bond L.W., Burnett R.W., Keech R.C., Bowers G.N. Jr. Determination of the molar absorptivity of NADH // Clin Chem. – 1976. – Vol. 22, No. 2. – P. 141–150.McComb RB, Bond LW, Burnett RW, Keech RC, Bowers GN Jr. Determination of the molar absorptivity of NADH. Clin Chem. 1976;22(2):141–50.Freyer D., Harms C. Kinetic Lactate Dehydrogenase Assay for Detection of Cell Damage in Primary Neuronal Cell Cultures // Bio Protoc. – 2017. – Vol. 7, No. 11. – P. e2308. DOI: 10.21769/BioProtoc.2308Freyer D, Harms C. Kinetic Lactate Dehydrogenase Assay for Detection of Cell Damage in Primary Neuronal Cell Cultures. Bio Protoc. 2017;7(11):e2308. DOI: 10.21769/BioProtoc.2308Potter T.M., Cedrone E., Neun B.W., Dobrovolskaia M.A. Detection of Nitric Oxide Production by the Macrophage Cell Line RAW264.7: Version 2. 2020. In: National Cancer Institute’s Nanotechnology Characterization Laboratory Assay Cascade Protocols [Internet]. Bethesda (MD): National Cancer Institute (US). – 2005. NCL Method ITA-7.Potter TM, Cedrone E, Neun BW, Dobrovolskaia MA. Detection of Nitric Oxide Production by the Macrophage Cell Line RAW264.7: Version 2. 2020 Sep. In: National Cancer Institute’s Nanotechnology Characterization Laboratory Assay Cascade Protocols [Internet]. Bethesda (MD): National Cancer Institute (US); 2005 May 1–. NCL Method ITA-7.Cho S.J., Roman G., Yeboah F., Konishi Y. The road to advanced glycation end products: a mechanistic perspective // Curr Med Chem. – 2007. – Vol. 14, No. 15. – P. 1653–1671. DOI: 10.2174/092986707780830989Cho SJ, Roman G, Yeboah F, Konishi Y. The road to advanced glycation end products: a mechanistic perspective. Curr Med Chem. 2007;14(15):1653–71. DOI: 10.2174/092986707780830989Yeh W.J., Hsia S.M., Lee W.H., Wu C.H. Polyphenols with antiglycation activity and mechanisms of action: A review of recent findings // J Food Drug Anal. – 2017. – Vol. 25, No. 1. – P. 84–92. DOI: 10.1016/j.jfda.2016.10.017Yeh WJ, Hsia SM, Lee WH, Wu CH. Polyphenols with antiglycation activity and mechanisms of action: A review of recent findings. J Food Drug Anal. 2017;25(1):84–92. DOI: 10.1016/j.jfda.2016.10.017Spasov A.A., Brel A.K., Litvinov R.A., Lisina S.V., Kucheryavenko A.F., Budaeva Yu.N., Salaznikova OA., Rashchenko A.I., Shamshina D.D., Batrakov V.V., Ivanov A.V. Evaluation of N-Hydroxy-, N-Metoxy-, and N-Acetoxybenzoyl-Substituted Derivatives of Thymine and Uracil as New Substances for Prevention and Treatment of Long-Term Complications of Diabetes Mellitus // Russ J Bioorg Chem. – 2018. – Vol. 44, No. 6. – P. 769–777. DOI: 10.1134/S1068162019010163Spasov AA, Brel AK, Litvinov RA, Lisina SV, Kucheryavenko AF, Budaeva YuN, Salaznikova OA, Rashchenko AI, Shamshina DD, Batrakov VV, Ivanov AV. Evaluation of N-Hydroxy-, N-Metoxy-, and N-Acetoxybenzoyl-Substituted Derivatives of Thymine and Uracil as New Substances for Prevention and Treatment of Long-Term Complications of Diabetes Mellitus. Russ J Bioorg Chem. 2018;44(6):769–777. DOI: 10.1134/S1068162019010163Wynn T.A., Ramalingam T.R. Mechanisms of fibrosis: therapeutic translation for fibrotic disease // Nat Med. – 2012. – Vol. 18, No. 7. – P. 1028–1040. DOI: 10.1038/nm.2807Wynn TA, Ramalingam TR. Mechanisms of fibrosis: therapeutic translation for fibrotic disease. Nat Med. 2012;18(7):1028–40. DOI: 10.1038/nm.2807Fournet M., Bonté F., Desmoulière A. Glycation Damage: A Possible Hub for Major Pathophysiological Disorders and Aging // Aging Dis. – 2018. – Vol. 9, No. 5. – P. 880–900. DOI: 10.14336/AD.2017.1121Fournet M, Bonté F, Desmoulière A. Glycation Damage: A Possible Hub for Major Pathophysiological Disorders and Aging. Aging Dis. 2018;9(5):880–900. DOI: 10.14336/AD.2017.1121Vona R., Pallotta L., Cappelletti M., Severi C., Matarrese P. The Impact of Oxidative Stress in Human Pathology: Focus on Gastrointestinal Disorders // Antioxidants (Basel). – 2021. – Vol. 10, No. 2. – P. 201. DOI: 10.3390/antiox10020201Vona R, Pallotta L, Cappelletti M, Severi C, Matarrese P. The Impact of Oxidative Stress in Human Pathology: Focus on Gastrointestinal Disorders. Antioxidants (Basel). 2021;10(2):201. DOI: 10.3390/antiox10020201Makena P., Kikalova T., Prasad G.L., Baxter S.A. Oxidative Stress and Lung Fibrosis: Towards an Adverse Outcome Pathway // Int J Mol Sci. – 2023. – Vol. 24, No. 15. – P. 12490. DOI: 10.3390/ijms241512490Makena P, Kikalova T, Prasad GL, Baxter SA. Oxidative Stress and Lung Fibrosis: Towards an Adverse Outcome Pathway. Int J Mol Sci. 2023;24(15):12490. DOI: 10.3390/ijms241512490Shroff A., Mamalis A., Jagdeo J. Oxidative Stress and Skin Fibrosis // Curr Pathobiol Rep. – 2014. – Vol. 2, No. 4. – P. 257–267. DOI: 10.1007/s40139-014-0062-yShroff A, Mamalis A, Jagdeo J. Oxidative Stress and Skin Fibrosis. Curr Pathobiol Rep. 2014;2(4):257–267. DOI: 10.1007/s40139-014-0062-yVerzijl N., DeGroot J., Ben Z.C., Brau-Benjamin O., Maroudas A., Bank R.A., Mizrahi J., Schalkwijk C.G., Thorpe S.R., Baynes J.W., Bijlsma J.W., Lafeber F.P., TeKoppele J.M. Crosslinking by advanced glycation end products increases the stiffness of the collagen network in human articular cartilage: a possible mechanism through which age is a risk factor for osteoarthritis // Arthritis Rheum. – 2002. – Vol. 46, No. 1. – P. 114–123. DOI: 10.1002/1529-0131(200201)46:1<114::AID-ART10025>3.0.CO;2-PVerzijl N, DeGroot J, Ben ZC, Brau-Benjamin O, Maroudas A, Bank RA, Mizrahi J, Schalkwijk CG, Thorpe SR, Baynes JW, Bijlsma JW, Lafeber FP, TeKoppele JM. Crosslinking by advanced glycation end products increases the stiffness of the collagen network in human articular cartilage: a possible mechanism through which age is a risk factor for osteoarthritis. Arthritis Rheum. 2002;46(1):114–23. DOI: 10.1002/1529-0131(200201)46:1<114::AID-ART10025>3.0.CO;2-PLloyd S.M., He Y. Exploring Extracellular Matrix Crosslinking as a Therapeutic Approach to Fibrosis // Cells. – 2024. – Vol. 13, No. 5. – P. 438. DOI: 10.3390/cells13050438Lloyd SM, He Y. Exploring Extracellular Matrix Crosslinking as a Therapeutic Approach to Fibrosis. Cells. 2024;13(5):438. DOI: 10.3390/cells13050438Lyu C., Kong W., Liu Z., Wang S., Zhao P., Liang K., Niu Y., Yang W., Xiang C., Hu X., Li X., Du Y. Advanced glycation end-products as mediators of the aberrant crosslinking of extracellular matrix in scarred liver tissue // Nat Biomed Eng. – 2023. – Vol. 7, No. 11. – P. 1437–1454. DOI: 10.1038/s41551-023-01019-zLyu C, Kong W, Liu Z, Wang S, Zhao P, Liang K, Niu Y, Yang W, Xiang C, Hu X, Li X, Du Y. Advanced glycation end-products as mediators of the aberrant crosslinking of extracellular matrix in scarred liver tissue. Nat Biomed Eng. 2023;7(11):1437–1454. DOI: 10.1038/s41551-023-01019-zWang K., Wen D., Xu X., Zhao R., Jiang F., Yuan S., Zhang Y., Gao Y., Li Q. Extracellular matrix stiffness-The central cue for skin fibrosis // Front Mol Biosci. – 2023. – Vol. 10. – P. 1132353. DOI: 10.3389/fmolb.2023.1132353Wang K, Wen D, Xu X, Zhao R, Jiang F, Yuan S, Zhang Y, Gao Y, Li Q. Extracellular matrix stiffness-The central cue for skin fibrosis. Front Mol Biosci. 2023;10:1132353. DOI: 10.3389/fmolb.2023.1132353Liu R.M., Desai L.P. Reciprocal regulation of TGF-β and reactive oxygen species: A perverse cycle for fibrosis // Redox Biol. – 2015. – Vol. 6. – P. 565–577. DOI: 10.1016/j.redox.2015.09.009Liu RM, Desai LP. Reciprocal regulation of TGF-β and reactive oxygen species: A perverse cycle for fibrosis. Redox Biol. 2015;6:565–577. DOI: 10.1016/j.redox.2015.09.009Dong H., Zhang Y., Huang Y., Deng H. Pathophysiology of RAGE in inflammatory diseases // Front Immunol. – 2022. – Vol. 13. – P. 931473. DOI: 10.3389/fimmu.2022.931473Dong H, Zhang Y, Huang Y, Deng H. Pathophysiology of RAGE in inflammatory diseases. Front Immunol. 2022;13:931473. DOI: 10.3389/fimmu.2022.931473Richter K., Kietzmann T. Reactive oxygen species and fibrosis: further evidence of a significant liaison // Cell Tissue Res. – 2016. – Vol. 365, No. 3. – P. 591–605. DOI: 10.1007/s00441-016-2445-3Richter K, Kietzmann T. Reactive oxygen species and fibrosis: further evidence of a significant liaison. Cell Tissue Res. 2016;365(3):591–605. DOI: 10.1007/s00441-016-2445-3Peng X., Ma J., Chen F., Wang M. Naturally occurring inhibitors against the formation of advanced glycation end-products // Food Funct. – 2011. – Vol. 2, No. 6. – P. 289–301. DOI: 10.1039/c1fo10034cPeng X, Ma J, Chen F, Wang M. Naturally occurring inhibitors against the formation of advanced glycation end-products. Food Funct. 2011;2(6):289–301. DOI: 10.1039/c1fo10034cAugustyniak A., Bartosz G., Cipak A., Duburs G., Horáková L., Luczaj W., Majekova M., Odysseos A.D., Rackova L., Skrzydlewska E., Stefek M., Strosová M., Tirzitis G., Venskutonis P.R., Viskupicova J., Vraka P.S., Zarković N. Natural and synthetic antioxidants: an updated overview // Free Radic Res. – 2010. – Vol. 44, No. 10. – P. 1216–1262. DOI: 10.3109/10715762.2010.508495Augustyniak A, Bartosz G, Cipak A, Duburs G, Horáková L, Luczaj W, Majekova M, Odysseos AD, Rackova L, Skrzydlewska E, Stefek M, Strosová M, Tirzitis G, Venskutonis PR, Viskupicova J, Vraka PS, Zarković N. Natural and synthetic antioxidants: an updated overview. Free Radic Res. 2010;44(10):1216–62. DOI: 10.3109/10715762.2010.508495Reddy V.P., Garrett M.R., Perry G., Smith M.A. Carnosine: a versatile antioxidant and antiglycating agent // Sci Aging Knowledge Environ. – 2005. – Vol. 2005, No. 18. – P. pe12. DOI: 10.1126/sageke.2005.18.pe12Reddy VP, Garrett MR, Perry G, Smith MA. Carnosine: a versatile antioxidant and antiglycating agent. Sci Aging Knowledge Environ. 2005;2005(18):pe12. DOI: 10.1126/sageke.2005.18.pe12Kosmachevskaya O.V., Nasybullina E.I., Pugachenko I.S., Novikova N.N., Topunov A.F. Antiglycation and Antioxidant Effect of Nitroxyl towards Hemoglobin //Antioxidants (Basel). – 2022. – Vol. 11, No. 10. – P. 2007. DOI: 10.3390/antiox11102007Kosmachevskaya OV, Nasybullina EI, Pugachenko IS, Novikova NN, Topunov AF. Antiglycation and Antioxidant Effect of Nitroxyl towards Hemoglobin. Antioxidants (Basel). 2022;11(10):2007. DOI: 10.3390/antiox11102007Liu H., Huo X., Wang S., Yin Z. The inhibitory effects of natural antioxidants on protein glycation as well as aggregation induced by methylglyoxal and underlying mechanisms // Colloids Surf B Biointerfaces. – 2022. – Vol. 212. – P. 112360. DOI: 10.1016/j.colsurfb.2022.112360Liu H, Huo X, Wang S, Yin Z. The inhibitory effects of natural antioxidants on protein glycation as well as aggregation induced by methylglyoxal and underlying mechanisms. Colloids Surf B Biointerfaces. 2022;212:112360. DOI: 10.1016/j.colsurfb.2022.112360Intagliata S., Spadaro A., Lorenti M., Panico A., Siciliano E.A., Barbagallo S., Macaluso B., Kamble S.H., Modica M.N., Montenegro L. In Vitro Antioxidant and Anti-Glycation Activity of Resveratrol and Its Novel Triester with Trolox //Antioxidants (Basel). – 2020. – Vol. 10, No. 1. – P. 12. DOI: 10.3390/antiox10010012Intagliata S, Spadaro A, Lorenti M, Panico A, Siciliano EA, Barbagallo S, Macaluso B, Kamble SH, Modica MN, Montenegro L. In Vitro Antioxidant and Anti-Glycation Activity of Resveratrol and Its Novel Triester with Trolox. Antioxidants (Basel). 2020;10(1):12. DOI: 10.3390/antiox10010012Caruso G., Di Pietro L., Cardaci V., Maugeri S., Caraci F. The therapeutic potential of carnosine: Focus on cellular and molecular mechanisms // Curr Res Pharmacol Drug Discov. – 2023. – Vol. 4. – P. 100153. DOI: 10.1016/j.crphar.2023.100153Caruso G, Di Pietro L, Cardaci V, Maugeri S, Caraci F. The therapeutic potential of carnosine: Focus on cellular and molecular mechanisms. Curr Res Pharmacol Drug Discov. 2023;4:100153. DOI: 10.1016/j.crphar.2023.100153Sirangelo I., Borriello M., Liccardo M., Scafuro M., Russo P., Iannuzzi C. Hydroxytyrosol Selectively Affects Non-Enzymatic Glycation in Human Insulin and Protects by AGEs Cytotoxicity // Antioxidants (Basel). – 2021. – Vol. 10, No. 7. – P. 1127. DOI: 10.3390/antiox10071127Sirangelo I, Borriello M, Liccardo M, Scafuro M, Russo P, Iannuzzi C. Hydroxytyrosol Selectively Affects Non-Enzymatic Glycation in Human Insulin and Protects by AGEs Cytotoxicity. Antioxidants (Basel). 2021;10(7):1127. DOI: 10.3390/antiox10071127Ibragimova U.M., Valuisky N.V., Sorokina S.A., Zhukova X.I., Raiberg V.R., Litvinov R.A. Antiglycation Activity of Isoindole Derivatives and Its Prediction Using Frontier Molecular Orbital Energies. Mol Biol (Mosk). – 2024. – Vol. 58, No. 6. – P. 1052–1060. DOI: 10.1134/S0026893324700638Ibragimova UM, Valuisky NV, Sorokina SA, Zhukova XI, Raiberg VR, Litvinov RA. [Antiglycation Activity of Isoindole Derivatives and Its Prediction Using Frontier Molecular Orbital Energies]. Mol Biol (Mosk). 2024;58(6):1052–1060. RussianSpeck K., Magauer T. The chemistry of isoindole natural products // Beilstein J Org Chem. – 2013. – Vol. 9. – P. 2048–2078. DOI: 10.3762/bjoc.9.243Speck K, Magauer T. The chemistry of isoindole natural products. Beilstein J Org Chem. 2013;9:2048–78. DOI: 10.3762/bjoc.9.243

The authors declare that there are no conflicts of interest present.