A facile synthesis and microtubule-destabilizing properties of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines

A facile synthesis and microtubule-destabilizing properties of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines Научная публикация

Журнал

European Journal of Medicinal Chemistry
ISSN: 1768-3254 , E-ISSN: 0223-5234

Вых. Данные

Год: 2015, Том: 94, Страницы: 237-251 Страниц : 15 DOI: 10.1016/j.ejmech.2015.02.051

Авторы

Stepanov Andrei I. ¹ , Astrat'ev Alexander A. ¹ , Sheremetev Aleksei B. ² , Lagutina Nataliya K. ³ , Palysaeva Nadezhda V. ² , Tyurin Aleksei Yu. ² , Aleksandrova Nataliya S. ² , Sadchikova Nataliya P. ³ , Suponitsky Kyrill Yu. ⁴ , Atamanenko Olga P. ² , Konyushkin Leonid D. ² , Semenov Roman V. ² , Firgang Sergei I. ² , Kiselyov Alex S. ⁵ , Semenova Marina N. ⁶ , Semenov Victor V. ²

Организации

1	Special Design and Construction Bureau SDCB "Technolog", 33-A Sovetskii Ave., Saint Petersburg 192076, Russian Federation
2	N. D. Zelinsky Institute of Organic Chemistry, RAS, 47 Leninsky Prospect, 119991 Moscow, Russian Federation
3	I. M. Sechenov First Moscow State Medical University, Trubetskaya Str. 8-2, 119991 Moscow, Russian Federation
4	A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilov Str., 119991 Moscow, Russian Federation
5	Department of Biological and Medicinal Chemistry, Moscow Institute of Physics and Technology, Institutsky Per. 9, Dolgoprudny, Moscow Region 141700, Russian Federation
6	N. K. Kol'tsov Institute of Developmental Biology, RAS, Vavilov Str., 26, 119334 Moscow, Russian Federation

A series of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines (BIFAs) were prepared in good yields (60–90% for each reaction step) via a novel procedure from aminofurazanyl hydroximoyl chlorides and o-diaminobenzenes. The synthetic sequence was run under mild reaction conditions, it was robust and did not require extensive purification of intermediates or final products. Furthermore, there was no need for protection of reactive moieties allowing for the parallel synthesis of diverse BIFA derivatives. Subsequent biological evaluation of the resulting compounds revealed their anti-proliferative effects in the sea urchin embryo model and in cultured human cancer cell lines. The most active compounds showed 0.2–2 μM activities in both assay systems. The unsubstituted benzene ring of the benzoimidazole template as well as the unsubstituted amino group in the furazan ring were essential prerequisites for the antimitotic activity of BIFAs. Compound 57 bearing the 2-chlorophenyl acetamide substituent at the nitrogen atom of the imidazole ring was the most active molecule in the examined set.

Stepanov A.I. , Astrat'ev A.A. , Sheremetev A.B. , Lagutina N.K. , Palysaeva N.V. , Tyurin A.Y. , Aleksandrova N.S. , Sadchikova N.P. , Suponitsky K.Y. , Atamanenko O.P. , Konyushkin L.D. , Semenov R.V. , Firgang S.I. , Kiselyov A.S. , Semenova M.N. , Semenov V.V.
A facile synthesis and microtubule-destabilizing properties of 4-(1H-benzo[d]imidazol-2-yl)-furazan-3-amines
European Journal of Medicinal Chemistry. 2015. V.94. P.237-251. DOI: 10.1016/j.ejmech.2015.02.051 WOS Scopus OpenAlex

Web of science:	WOS:000353730900022
Scopus:	2-s2.0-84924740553
OpenAlex:	W1985376820

БД	Цитирований
OpenAlex	27
Scopus	31
Web of science	25