Events The 25th International Electronic Conference on Synthetic Organic Chemistry

Event submissions

Published

This submission belongs to the session S1. General Organic Synthesis of the event The 25th International Electronic Conference on Synthetic Organic Chemistry

Published date

14 Nov, 2021

Academic Editor

Julio A. Seijas

Citation

Ilgiz Islamov, Adelya Yusupova, Lilya Dzhemileva, Usein Dzhemilev, Targeted synthesis and antitumor activity in vitro of macrodiolides containing 1Z,5Z-diene and 1,3-diyne moieties, in Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry, 15 November–30 November 2021, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-25-11704

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Targeted synthesis and antitumor activity in vitro of macrodiolides containing 1Z,5Z-diene and 1,3-diyne moieties

Ilgiz Islamov ¹

Adelya Yusupova ¹

Lilya Dzhemileva ¹

Usein Dzhemilev ¹

1. Institute of Petrochemistry and Catalysis, Russian Academy of Sciences

Abstract

Efficient methods have been developed for synthesizing hither to unknown macrodiolides incorporating 1Z,5Z-diene and 1,3-diyne moieties in 55-79% yields and with >98% stereoselectivity by intermolecular cyclocondesation of (7Z,11Z)-octadeca-7,11-dienedioic acid with α,ω-diols catalyzed by hafnium triflate Hf(OTf)4, as well as by oxidative coupling of α,ω-diynes obtained by esterification of (7Z,11Z)-octadeca-7,11-dienedioic acid with alkynols. The macrodiolides synthesized exhibit in vitro cytotoxic activity toward Jurkat, K562, U937, HL-60, HeLa and Hek293 cell lines.

Keywords

1,5-Dienoic compounds

Homogeneous catalysis

Cyclomagnesiation

Macrodiolides

Cytotoxicity

Manuscript

sciforum_050780_original_ECCOS_1_Eng - done.pdf

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