A unique dithiocarbamate chemistry during design & synthesis of novel sperm-immobilizing agents#
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
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Creator |
Jangir, Santosh
Bala, Veenu Lal, Nand Kumar, Lalit Sarswat, Amit Kumar, Lokesh Kushwaha, Bhavana Singh, Pratiksha Shukla, P K Maikhuri, J P Gupta, Gopal Sharma, V L |
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Date |
2014-06-19T11:05:36Z
2014-06-19T11:05:36Z 2014 |
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Identifier |
Organic & Biomolecular Chemistry, 2014, 12, 3090–3099
http://hdl.handle.net/123456789/1282 |
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Description |
- 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. 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.
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358651 bytes
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Language |
en
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Relation |
CSIR-CDRI Communication no. 8627
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Subject |
Unique Dithiocarbamate Chemistry
Design & Synthesis Novel Sperm-Immobilizing Agents |
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Title |
A unique dithiocarbamate chemistry during design & synthesis of novel sperm-immobilizing agents#
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Type |
Article
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