danДоклады Национальной академии наук БеларусиDoklady of the National Academy of Sciences of Belarus1561-83232524-2431The Republican Unitary Enterprise Publishing House "Belaruskaya Navuka"10.29235/1561-8323-2019-63-3-291-297dan-614Research ArticleХИМИЯCHEMISTRYСинтоны для новых 11-дезокси-3-окса-3,7-интер-м-фениленовых аналогов простагландиновSynthons for new 11-deoxy-3-oxa-3,7-inter-m-phenylene prostaglandin analoguesПашковскийФ. С.PashkovskyF. S.

Пашковский Феликс Сигизмундович – канд. хим. наук, заведующий лабораторией

ул. Купревича, 5/2, 220141, Минск, Республика Беларусь

Pashkovsky Felix Sigizmundovich – Ph. D. (Chemistry), Head of the Laboratory

5/2, Kuprevich Str., 220141, Minsk, Republic of Belarus

pashkovsky61@mail.ruКорнеевД. И.KorneevD. I.

Корнеев Дмитрий Игоревич – мл. науч. сотрудник

ул. Купревича, 5/2, 220141, Минск, Республика Беларусь

Korneev Dmitry Igorevich– Junior researcher

5/2, Kuprevich Str., 220141, Minsk, Republic of Belarus

nocterumm@gmail.comЛахвичФ. А.LakhvichF. A.

Лахвич Федор Адамович – академик, д-р хим. наук, профессор, гл. науч. сотрудник

ул. Купревича, 5/2, 220141, Минск, Республика Беларусь

Lakhvich Fedor Adamovich – Academician, D. Sc. (Chemistry), Professor, Chief researcher

5/2, Kuprevich Str., 220141, Minsk, Republic of Belarus

lakhvich@iboch.byИнститут биоорганической химии Национальной академии наук БеларусиInstitute of Bioorganic Chemistry of the National Academy of Sciences of Belarus201927062019633291297Copyright © Пашковский Ф.С., Корнеев Д.И., Лахвич Ф.А., 20192019Пашковский Ф.С., Корнеев Д.И., Лахвич Ф.А.Pashkovsky F.S., Korneev D.I., Lakhvich F.A.Данная работа распространяется под лицензией Creative Commons Attribution 4.0.This work is licensed under a Creative Commons Attribution 4.0 License.https://doklady.belnauka.by/jour/article/view/614

Разработана схема синтеза циклопентеноновых синтонов для метаболически стабильных 11-де з-окси-3-окса-3,7-интер-м-фениленовых аналогов простагландинов. Ключевой стадией схемы является конденсация циклопентан-1,3-диона с легко доступным метиловым эфиром 3-(формилфенокси)уксусной кислоты по Кневенагелю в присутствии эфира Ганча.

A synthetic scheme for obtaining cyclopentenone synthons for metabolically stable 11-deoxy-3-oxa-3,7-inter-m-phenylene prostaglandin analogues has been developed. The key step of the scheme is the Knoevenagel condensation of cyclopentane-1,3-dione with the readily available 3-(formylphenoxy)acetic acid methyl ester in the presence of Hantzsh ester.

циклопентан-13-дионметиловый эфир 3-(формилфенокси)уксусной кислотыэфир Ганчаконденсация по Кневенагелюциклопентеноновые синтоныинтерфениленовые аналоги простагландиновcyclopentane-13-dione3-(formylphenoxy)acetic acid methyl esterHantzsh esterKnoevenagel condensationcyclopentenone synthonsinterphenylene prostaglandin analoguesReferencesGe, Y.-Y. Progress in the Total Synthesis of Prostaglandins / Y.-Y. Ge, Z.-Y. Cai, W.-C. Zhou // Chin. J. Pharm. – 2013. – Vol. 44, N 7. – P. 720–728.Ge Y.-Y., Cai Z.-Y., Zhou W.-C. Progress in the Total Synthesis of Prostaglandins. Chinese Journal of Pharmaceuticals, 2013, vol. 44, no. 7, pp. 720–728.Collins, P. W. Synthesis of Therapeutically Useful Prostaglandin and Prostacyclin Analogs / P. W. Collins, S. W. Djuric // Chem. Rev. – 1993. – Vol. 93, N 4. – P. 1533–1564. https://doi.org/10.1021/cr00020a007Collins P. W., Djuric S. W. Synthesis of Therapeutically Useful Prostaglandin and Prostacyclin Analogs. Chemical Reviews, 1993, vol. 93, no. 4, pp. 1533–1564. https://doi.org/10.1021/cr00020a007Budev, M. M. Overview of treprostinil sodium for the treatment of pulmonary arterial hypertension / M. M. Budev, O. A. Minai, A. C. Arroliga // Drugs Today (Barc). – 2004. – Vol. 40, N 3. – P. 225–234. https://doi.org/10.1358/dot.2004.40.3.820086Budev M. M., Minai O. A., Arroliga A. C. Overview of treprostinil sodium for the treatment of pulmonary arterial hypertension. Drugs of Today (Barcelona), 2004, vol. 40, no. 3, pp. 225–234. https://doi.org/10.1358/dot.2004.40.3.820086Melian, E. B. Beraprost: a review of its pharmacology and therapeutic efficacy in the treatment of peripheral arterial desease and pulmonary arterial hypertension / E. B. Melian, K. L. Goa // Drugs. – 2002. – Vol. 62, N 1. – P. 107–133. https://doi.org/10.2165/00003495-200262010-00005Melian E. B., Goa K. L. Beraprost: a review of its pharmacology and therapeutic efficacy in the treatment of peripheral arterial desease and pulmonary arterial hypertension. Drugs, 20 02 , vol. 62 , no. 1, p p. 107–133. https://doi.org/10.2165/00003495-200262010-00005Analytic review of bimatoprost, latanoprost and travoprost in primary open angle glaucoma / S. Holmstrom [et al.] // Curr. Med. Res. opin. – 2005. – Vol. 21, N 11. – P. 1875–1883. https://doi.org/10.1185/030079905x65600Holmstrom S., Buchholz P., Walt J., Wickstrøm J., Aagren M. Analytic review of bimatoprost, latanoprost and travoprost in primary open angle glaucoma. Current Medical Research and Opinion, 2005, vol. 21, no. 11, pp. 1875–1883. https://doi.org/10.1185/030079905x65600Curran, M. P. Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension / M. P. Curran // Drugs Aging. – 2009. – Vol. 26, N 12. – P. 1049–1071. https://doi.org/10.2165/11203210-000000000-00000Curran M. P. Bimatoprost: a review of its use in open-angle glaucoma and ocular hypertension. Drugs and Aging, 2009, vol. 26, no. 12, pp. 1049–1071. https://doi.org/10.2165/11203210-000000000-00000Tafluprost for glaucoma / M. Papadia [et al.] // Expert. opin. Pharmacother. – 2011. – Vol. 12, N 15. – P. 2393–2401. https://doi.org/10.1517/14656566.2011.606810Papadia M., Bagnis A., Scotto R., Traverso C. E. Tafluprost for glaucoma. Expert Opinion on Pharmacotherapy, 2011, vol. 12, no. 15, pp. 2393–2401. https://doi.org/10.1517/14656566.2011.606810Простагландины и их аналоги в репродукции животных и человека / Г. А. Толстиков [и др.]. – Уфа, 1989. – 400 c.Тolstikov G. A., Мiftakchov М. S., Lazareva D. N., Pomoinetskii V. D., Sidorov N. N. Prostaglandins and their analogues in reproduction of animals and humans. Ufa, 1989. 400 p. (in Russian).Простаноиды. XI. Синтез некоторых о-интерфенилен-оксааналогов 11-дезоксипростагландина Е 1 / Г. А. Толстиков [и др.] // ЖОрХ. – 1984. – Т. 20, вып. 11. – С. 2285–2295.Тolstikov G. A., Мiftakchov М. S., Adler M. E., Sidorov N. N. Prostanoids. XI. Synthesis of some o-interphenylene-oxa-analogues of 11-deoxyprostaglandin Е 1 . Zhurnal Organicheskoi Khimii = Russian Journal of Organic Chemistry, 1984, vol. 20, no. 11, pp. 2285–2295 (in Russian).Лахвич, Ф. А. Гетеропростаноиды: синтез и биологическая активность / Ф. А. Лахвич, Ф. С. Пашковский, Е. В. Королева // Усп. хим. – 1992. – Т. 61, вып. 2. – С. 456–495.Lakhvich F. A., Pashkovsky F. S., Koroleva E. V. Heteroprostanoids: synthesis and biological activity. Russian Chemical Reviews, 1992, vol. 61, no. 2, pp. 243–266 https://doi.org/10.1070/rc1992v061n02abeh000943Пашковский, Ф. С. Синтез предшественников 3,7-интерфениленовых гетеропростаноидов на основе тетроновых кислот / Ф. С. Пашковский, М. Г. Грибовский, Ф. А. Лахвич // Докл. Нац. акад. наук Беларуси. – 2006. – Т. 50, № 3. – С. 69–72.Pashkovsky F. S., Gribovsky M. G., Lakhvich F. A. Synthesis of 3,7-interphenylene heteroprostanoid precursors on the basis of tetronic acids. Doklady Natsional’noi akademii nauk Belarusi = Doklady of the National Academy of Sciences of Belarus, 2006, vol. 50, no. 3, pp. 69–72 (in Russian).Гетероциклические аналоги простагландинов. IV. Синтез 3,7-интерфениленовых 3,10(11)-диокса-13-азапростаноидов и 9-окса-7-азапростаноидов на основе тетроновой кислоты и ароматических альдегидов / Ф. С. Пашковский [и др.] // ЖОрХ. – 2008. – Т. 44, вып. 5. – С. 667–680.Pashkovskii F. S., Shchukina E. M., Gribovskii M. G., Lakhvich F. A. Heterocyclic analogs of prostaglandines: IV. Synthesis of 3,7-interphenylene 3,10(11)-dioxa-13-azaprostanoids and 9-oxa-7-azaprostanoids based on tetronic acid and aromatic aldehydes. Russian Journal of Organic Chemistry, 2008, vol. 44, no. 5, pp. 657–670. https://doi.org/10.1134/s1070428008050047Zheng, C. Transfer hydrogenation with Hantzsch esters and related organic hydride donors / C. Zheng, S.-L. You // Chem. Soc. Rev. – 2012. – Vol. 41, N 6. – P. 2498–2518. https://doi.org/10.1039/c1cs15268hZheng C., You S.-L. Transfer hydrogenation with Hantzsch esters and related organic hydride donors. Chemical Society Reviews, 2012, vol. 41, no. 6, pp. 2498–2518. https://doi.org/10.1039/c1cs15268hЛахвич, Ф. А. 11-Дезокси-13,15-изоксазолопростаноиды с функционализированной α-цепью на основе 2-ацетил циклопентан-1,3-диона и фурфурола / Ф. А. Лахвич, Ф. С. Пашковский, Л. Г. Лис // ЖОрХ. – 1992. – Т. 28, вып. 12. – С. 2483–2489.Lakhvich F. A., Pashkovsky F. S., Liss L. G. 11-Deoxy-13,15-isoxazoloprostanoids with functionalized α-chain on the basis of 2-acetylcyclopentane-1,3-dione and furfural. Zhurnal Organicheskoi Khimii = Russian Journal of Organic Chemistry, 1992, vol. 28, no. 12, pp. 2483–2489 (in Russian).Cheng, M.-F. Liquid-Phase Combinatorial Synthesis of 1,4-Benzodiazepine-2,5-diones as the Candidates of Endothelin Receptor Antagonism / M.-F. Cheng, J.-M. Fang // J. Comb. Chem. – 2004. – Vol. 6, N 1. – P. 99–104. https://doi.org/10.1021/cc030034dCheng M.-F., Fang J.-M. Liquid-Phase Combinatorial Synthesis of 1,4-Benzodiazepine-2,5-diones as the Candidates of Endothelin Receptor Antagonism. Journal of Combinatorial Chemistry, 2004, vol. 6, no. 1, pp. 99–104. https://doi.org/10.1021/cc030034d

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