Synthesis and bioactivities of novel piperazine-containing 1,5-Diphenyl-2-penten-1-one analogues from natural product lead

Bioorganic & Medicinal Chemistry Letters
Gaofei XuYun Ling

Abstract

A series of novel 1,5-Diphenyl-2-penten-1-one analogues (7a-h, 8a-h) with piperazine moiety have been designed and synthesized on the basis of natural product 1,5-Diphenyl-2-penten-1-one (I). All the synthesized compounds were evaluated in vitro for anti-plant pathogenic fungi activities and insecticidal activities. The results indicated that most of these analogues exhibited moderate antifungal activities and moderate to good insecticidal activities. Amongst them, the most potent 7c, 7e and 7h keep a mortality of 100% against larva of mosquito at the concentration of 1mg/L. Initial structure-activity relationship (SAR) analysis showed that, a methyl group can influence the biological activities of these compounds significantly, the compounds with N'-unsubstituted piperazine showed much better antifungal activities and larvicidal activity against mosquito than the compounds with N'-methylated piperazine. In addition, the larvicidal activity against mosquito had sharply decline when the substituent on benzene ring was changed from 4-position to 2 or 3-position.

Citations

Apr 19, 2020·Current Pharmaceutical Design·Anjali SharmaAvneet Kaur
Jun 4, 2021·Journal of Enzyme Inhibition and Medicinal Chemistry·Run-Hui ZhangZhe-Shan Quan
Jun 18, 2021·Journal of Pesticide Science·Jun SuzukiMiwa Onoue
Jul 25, 2021·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Saúl A Luna-HernándezJosé L Olivares-Romero
Aug 30, 2019·The Journal of Organic Chemistry·Ashokkumar PalanivelDerrick L J Clive
Aug 14, 2020·The Journal of Organic Chemistry·Masaki KobayashiYasushi Obora

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