Synthesis of ( S )- N -ethyl-2-(5-methylene-4-oxocyclopent-2-en-1-yl)acetamide – a model exomethylidencyclopentenone bioisoster of prostamides

A. M. Gimazetdinov; Гимазетдинов Айрат Маратович; Z. R. Makaev; Макаев Зайнутдин Рамилевич; M. S. Miftakhov; Мифтахов М. С.

doi:10.31857/S0514749225030049

Synthesis of (S)-N-ethyl-2-(5-methylene-4-oxocyclopent-2-en-1-yl)acetamide – a model exomethylidencyclopentenone bioisoster of prostamides

Authors: Gimazetdinov A.M.¹, Makaev Z.R.¹, Miftakhov M.S.¹
Affiliations:
1. UFRS RAS
Issue: Vol 61, No 3 (2025)
Pages: 246-252
Section: ЭКСПЕРИМЕНТАЛЬНЫЕ СТАТЬИ
URL: https://bioethicsjournal.ru/0514-7492/article/view/687792
DOI: https://doi.org/10.31857/S0514749225030049
EDN: https://elibrary.ru/ETTOTN
ID: 687792

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription or Fee Access

Abstract
Full Text
About the authors
References
Supplementary files
Statistics

Abstract

The synthesis of the exo-methylidenecyclopentenone amide given in the title of the article from the methyl ester 2-{(1R,2R,5R)-2-[((tert-butyl(dimethyl)silyloxymethyl]-5-(trimethylsilyl)cyclopent-3-en-1-yl}acetic acid.

Keywords

allylsilanes, bicyclic δ-lactones, exo-methylidencyclopentenones, cross-conjugated cyclopentenones, prostamides

Full Text

About the authors

A. M. Gimazetdinov

UFRS RAS

Author for correspondence.
Email: gimazetdinov@anrb.ru
ORCID iD: 0000-0002-8539-3442

Ufa Institute of Chemistry

Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

Z. R. Makaev

UFRS RAS

Email: gimazetdinov@anrb.ru
ORCID iD: 0000-0002-0958-3164

Ufa Institute of Chemistry

Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

M. S. Miftakhov

UFRS RAS

Email: gimazetdinov@anrb.ru

Ufa Institute of Chemistry

Russian Federation, prosp. Oktyabrya, 71, Ufa, 450054

References

Gimazetdinov A.M., Khalfitdinova L.A., Miftakhov M.S. Mendeleev Commun. 2013, 23, 321–322. doi: 10.1016/j.tet.2013.09.047
Vostricov N.S., Spirikhin L.V., Lobov A.N., Gimazetdinov A.M., Zileeva Z.R., Vakhitova Y.V., Macaev Z.R., Pivnitsky K.K., Miftakhov M.S. Mendeleev Commun. 2019, 29, 372–374. doi: 10.1016/j.mencom.2019.07.003
Лоза В.В., Гимазетдинов А.М., Мифтахов М.С. ЖОрХ. 2018, 54, 1575–1620. [Loza V.V., Gimazetdinov A.M., Miftakhov M.S. Russ. J. Org. Chem. 2018, 54, 1585–1629.] doi: 10.1134/S1070428018110015
Bie Q., Dong H., Jin C., Zhang H., Zhang B. Am. J. Transl. Res. 2018, 10, 648–658
Ladin D.A., Soliman E., Escobedo R., Fitzgerald T.L., Yang L.V., Burns C., Dross R.V. Mol. Cancer Ther. 2017, 16, 838–849. doi: 10.1158/1535-7163.MCT-16-0484
Ladin D.A., Nelson M.M., Cota E., Colonna C., Burns C., Robidoux J., Fisher-Wellman K.H., Van Dross-Anderson R. Oncotarget. 2022, 13, 1380–1396. doi: 10.18632/oncotarget.28334
Gimazetdinov A.M., Gataullin S.S., Bushmarinov I.S., Miftakhov M.S. Tetrahedron. 2012, 68, 5754–5758. doi: 10.1016/j.tet.2012.05.036
Гимазетдинов А.М., Альмухаметов А.З., Мифтахов М.С. ЖОрХ. 2019, 55, 938–944. [Gimazetdinov A.M., Al’mukhametov A.Z., Miftakhov M.S. Russ. J. Org. Chem. 2019, 55, 831–836.] doi: 10.1134/S1070428019060137
Аралбаева Г.В., Альмухаметов А.З., Гимазетдинов А.М. ЖОрХ. 2022, 58, 1168–1180. [Aralbaeva G.V., Al’mukhametov A.Z., Gimazetdinov A.M. Russ. J. Org. Chem. 2022, 58, 1589–1599.] doi: 10.1134/S1070428022110057
Gimazetdinov A.M., Al’mukhametov A.Z., Loza V.V., Spirikhin L.V., Miftakhov M.S. Mendeleev Commun. 2018, 28, 546–547. doi: 10.1016/j.mencom.2018.09.033
Gimazetdinov A.M., Al’mukhametov A.Z., Miftakhov M.S. New J. Chem. 2022, 46, 6708–6714. doi: 10.1039/d2nj01003h