Furanolabdanoid-based 1,2,4-oxadiazoles: Synthesis and cytotoxic activity | Sciact

Furanolabdanoid-based 1,2,4-oxadiazoles: Synthesis and cytotoxic activity Научная публикация

Журнал

ChemistrySelect
ISSN: 2365-6549

Вых. Данные

Год: 2016, Том: 1, Номер: 3, Страницы: 417-424 Страниц : 8 DOI: 10.1002/slct.201600042

Ключевые слова

terpenes; furanolabdatrienes; 1,2,4-oxadiazoles; apoptosis; cytotoxicity

Авторы

Mironov Maxim E. ^1,2 , Pokrovsky Mikhail A. ² , Kharitonov Yurii V. ^1,2 , Shakirov Makhmut M. ¹ , Pokrovsky Andrey G. ² , Shults Elvira E. ^1,2

Организации

1	(Данные Web of science) Russian Acad Sci, Novosibirsk Organ Chem Inst, Med Chem Lab, Lavrentyev Ave 9, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, Dept Med, Pirogova St 2, Novosibirsk 630090, Russia

Several 15,16-epoxy- 8,13,14-labdatriene derivatives modified at the C-16 position with a 1,2,4-oxadiazole ring with various substituent in the 5-th position, were obtained via multistep synthesis from 16-formyl derivatives of natural diterpenoid lambertianic acid. The cytotoxicity of furanolabdanoid-based 1,2,4-oxadiazoles was evaluated against human cancer cells (CEM-13, MT-4, U-937, MCF-7, MDA-MB-231, MEL-8) using the conventional MTT assays. All the tested diterpenoid-oxadiazole hybrids displayed better cytotoxic activity then lambertianic acid. The activity and selectivity to the cell line increased even further in the compounds containing a chloromethyl substituent in the 5th position of the 1,2,4-oxadiazole ring. Two of the synthesized compounds exhibited high cytotoxic activity against lymphoblastoid cell line CEM-13 (GI50 0.08-0.34 mM), which was higher that than of the comparative drug Doxorubicin. The antitumor mechanism may be related to apoptosis induction in U-937, MCF-7, and CEM-13 cells.

Mironov M.E. , Pokrovsky M.A. , Kharitonov Y.V. , Shakirov M.M. , Pokrovsky A.G. , Shults E.E.
Furanolabdanoid-based 1,2,4-oxadiazoles: Synthesis and cytotoxic activity
ChemistrySelect. 2016. V.1. N3. P.417-424. DOI: 10.1002/slct.201600042 WOS Scopus РИНЦ OpenAlex

Опубликована в печати:	1 мар. 2016 г.
Опубликована online:	7 мар. 2016 г.

Web of science:	WOS:000395395200013
Scopus:	2-s2.0-85032717594
РИНЦ:	35506878
OpenAlex:	W2294968440

БД	Цитирований
Web of science	13
Scopus	12
OpenAlex	13