A unique dithiocarbamate chemistry during design & synthesis of novel sperm-immobilizing agents
| Autor: | Pratiksha Singh, Gopal Gupta, Veenu Bala, Vishnu L. Sharma, Nand Lal, Amit Sarswat, Santosh Jangir, Praveen K. Shukla, Bhavana Kushwaha, Lokesh Kumar, Jagdamba P. Maikhuri, Lalit Kumar |
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| Rok vydání: | 2014 |
| Předmět: |
Male
Antifungal Antifungal Agents medicine.drug_class Microbial Sensitivity Tests Biochemistry Piperazines Toxicology Structure-Activity Relationship Thiocarbamates medicine Humans Structure–activity relationship Sulfhydryl Compounds Sperm Immobilizing Agents Physical and Theoretical Chemistry Mode of action Dithiocarbamate Fluorescent Dyes chemistry.chemical_classification Cell Death Chemistry Organic Chemistry Spermatozoa Sperm Fluorescence Lactobacillus Design synthesis Drug Design Trichomonas HeLa Cells Nuclear chemistry |
| Zdroj: | Org. Biomol. Chem.. 12:3090-3099 |
| ISSN: | 1477-0539 1477-0520 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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