Synthesis and Antimicrobial Activity of Thiosulfinates, Allicin Analogues

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Diallyl thiosulfinate (allicin) effectively inhibits the growth of various microorganisms, including antibiotic-resistant strains, so it can be considered a broad-spectrum antimicrobial compound. However, its instability in the bloodstream hinders its use as a therapeutic agent. We have synthesized a number of allicin analogues, both natural and synthetic, and evaluated in vitro their antimicrobial properties against Staphylococcus aureus and Candida albicans. The synthesized compounds were shown to exhibited more pronounced antifungal activity than antibacterial one. Among the compounds obtained, synthetic di-(2,2,2-trichloroethyl) ester of 3,3'-[(thio)sulfinyl]dipropionic acid effectively inhibited the growth of both fungi and bacteria at concentrations comparable to those of known antimicrobial agents used in medical practice.

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作者简介

V. Puchkov

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

A. Lyfenko

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

V. Koval

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

S. Revtovich

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

V. Kulikova

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

N. Anufrieva

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

A. Zemskaya

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

E. Morozova

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

编辑信件的主要联系方式.
Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

P. Solyev

Engelhardt Institute of Molecular Biology of the Russian Academy of Sciences

Email: elmorozova@yahoo.com
俄罗斯联邦, Moscow, 119991

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2. Fig. 1. Scheme of synthesis of thiosulfinates. Reagents and general conditions: (i) H2O2, HCOOH, 0°C; (ii) m-CPBA, CH2Cl2, -78°C → 0°C; (iii) ROH, boiling, H2SO4. The output of the product is indicated in parentheses. Designations: Me ‒ methyl group, Et ‒ ethyl group, Pr ‒ propyl group, Allyl ‒ allyl group, Py-N-oxide ‒ pyridine-N-oxide, propionic acid ‒ propionic acid.

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