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Issue 19, 2014
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A unique dithiocarbamate chemistry during design & synthesis of novel sperm-immobilizing agents

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Abstract

1-Substituted piperazinecarbodithioates were obtained by an unusual removal of CS2 in benzyl substituted dithiocarbamate derivatives under acid and basic conditions during design and synthesis of 1,4-(disubstituted)piperazinedicarbodithioates as double edged spermicides. A plausible mechanism for CS2 removal has been proposed. All synthesized compounds were subjected to spermicidal, antitrichomonal and antifungal activities. Twenty-one compounds irreversibly immobilized 100% sperm (MEC, 0.06–31.6 mM) while seven compounds exhibited multiple activities. Benzyl 4-(2-(piperidin-1-yl)ethyl) piperazine-1-(carbodithioate) (18) and 1-benzyl 4-(2-(piperidin-1-yl)ethyl)piperazine-1,4-bis(carbodithioate) (24) exhibited appreciable spermicidal (MEC, 0.07 and 0.06 mM), antifungal (MIC, 0.069–0.14 and >0.11 mM) and antitrichomonal (MIC, 1.38 and 0.14 mM) activities. The probable mode of action of these compounds seems to be through sulfhydryl binding which was confirmed by fluorescence labeling of sperm thiols.

Graphical abstract: A unique dithiocarbamate chemistry during design & synthesis of novel sperm-immobilizing agents

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Publication details

The article was received on 02 Jan 2014, accepted on 06 Mar 2014 and first published on 06 Mar 2014


Article type: Paper
DOI: 10.1039/C4OB00005F
Author version available: Download Author version (PDF)
Citation: Org. Biomol. Chem., 2014,12, 3090-3099
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    A unique dithiocarbamate chemistry during design & synthesis of novel sperm-immobilizing agents

    S. Jangir, V. Bala, N. Lal, L. Kumar, A. Sarswat, L. Kumar, B. Kushwaha, P. Singh, P. K. Shukla, J. P. Maikhuri, G. Gupta and V. L. Sharma, Org. Biomol. Chem., 2014, 12, 3090
    DOI: 10.1039/C4OB00005F

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