Synthesis and Cytotoxicity of Sulfanyl, Sulfinyl and Sulfonyl Group Containing Ursane Conjugates with 1,3,4-Oxadiazoles and 1,2,4-Triazoles

Synthesis and Cytotoxicity of Sulfanyl, Sulfinyl and Sulfonyl Group Containing Ursane Conjugates with 1,3,4-Oxadiazoles and 1,2,4-Triazoles Full article

Journal

ChemistrySelect
ISSN: 2365-6549

Output data

Year: 2021, Volume: 6, Number: 25, Pages: 6472-6477 Pages count : 6 DOI: 10.1002/slct.202101594

Tags

Alkylation; Antiproliferative activity; Molecular modelling; Oxidation; Ursane-azole hybrids

Authors

Semenova Marya D. ¹ , Popov Sergey A. ¹ , Golubeva Tatiana S. ² , Baev Dmitry S. ¹ , Shults Elvira E. ¹ , Turks Māris ³

Affiliations

1	Novosibirsk Institute of Organic Chemistry, Acad. Lavrentyev ave. 9, Novosibirsk, 630090, Russian Federation
2	The Federal Research Center Institute of Cytology and Genetics, Acad. Lavrentyev Ave., 10, Novosibirsk, 630090, Russian Federation
3	Institute of Technology of Organic Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, P. Valdena Str. 3, Riga, LV-1048, Latvia

A library of novel sulfanyl, sulfinyl, and sulfonyl group-containing ursane conjugates with 1,3,4-oxadiazoles and 1,2,4-triazoles were designed and obtained. The target compounds were synthesized by alkylation of the corresponding azole-based thiones followed by S-selective oxidation. The expected sulfoxides and sulfones were obtained depending on the applied excess of mCPBA without oxidation of the ursane double bond. The novel products were studied for their antiproliferative activity on cell lines MCF7 (breast cancer), U-87 MG (glioblastoma multiform cells), A549 (lung carcinoma), and U-87 MG (hepatocarcinoma), using immortalized human fibroblasts hTERT as non-cancer control. Oxadiazole-derived methylsulfones possessed the most notable cytotoxicity, while the sulfanyl group containing ursane conjugates with 1,2,4-triazoles 7 g, 7 h exhibited the best selectivity and antiproliferative activity, superior to ursolic acid and starting azole-based thiones. Possible mechanism of action of thioethers 7 g, 7 h was studied using molecular modeling. © 2021 Wiley-VCH GmbH

Semenova M.D. , Popov S.A. , Golubeva T.S. , Baev D.S. , Shults E.E. , Turks M.
Synthesis and Cytotoxicity of Sulfanyl, Sulfinyl and Sulfonyl Group Containing Ursane Conjugates with 1,3,4-Oxadiazoles and 1,2,4-Triazoles
ChemistrySelect. 2021. V.6. N25. P.6472-6477. DOI: 10.1002/slct.202101594 WOS Scopus РИНЦ

Web of science	WOS:000674289000016
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