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1,2-Dithiolane
1,2-Dithiolane is an organosulfur compound with the formula . It is also classified as a heterocycle derived from cyclopentane by replacing two methylene bridges ( units) with a disulfide group. 1,3-Dithiolane is an isomer. The parent molecule is unimportant but substituted derivatives, especially lipoic acid and its derivatives, are often essential for life. Several occur naturally. The parent 1,2-dithiolane is the disulfide derived from 1,3-propanedithiol. It is however unstable with respect to oligomerization. In general, 1,3-dithiols are superior reductants relative to monothiols. Natural occurrence Many substituted 1,2-dithiolates are found in nature. The most common is lipoic acid, a chiral dithiolane, which features a pentanoic acid substituent. It is essential for aerobic metabolism in mammals. Some 1,2-dithiolane are found in some foods, such as asparagusic acid in asparagus. The 4-dimethylamino derivative nereistoxin was the inspiration for insecticides that ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
Nereistoxin
Nereistoxin is a natural product identified in 1962 as the toxic organic compound ''N'',''N''-dimethyl-1,2-dithiolan-4-amine. It had first been isolated in 1934 from the marine annelid ''Lumbriconereis heteropoda'' and acts by blocking the nicotinic acetylcholine receptor. Researchers at Takeda Pharmaceutical Company, Takeda in Japan investigated it as a possible insecticide. They subsequently developed a number of derivatives that were commercialised, including those with the International Organization for Standardization, ISO trivial name, common names bensultap, cartap, thiocyclam and thiosultap. Structures and synthesis Cartap.svg, Cartap Bensultap.svg, Bensultap Thiosultap.svg, Thiosultap Thiocyclam neutral.svg, Thiocyclam Bensultap (R=SO2Ph) was made by the reaction of the sodium salt of benzenethiolsulfonate (PhSO2SNa) with ''N'',''N''-dimethyl 1,3-dichloro-2-propylamine or ''N'',''N''-dimethyl 2,3-dichloropropylamine in ethanol. : Bensultap can be converted to nereistoxin ... [...More Info...] [...Related Items...] OR: [Wikipedia] [Google] [Baidu] |
