Synthesis and structure--activity relationship of nonyl 3-acyldithiocarbazates and related compounds for uncoupling activities.
Various nonyl 3-substituted-dithiocarbazates, methyl and dimethyl derivatives of nonyl 3-benzoyldithiocarbazate, nonyl 2-substituted-dithiocarbamates, and benzaldehyde nonyldithiocarbohydrazone were synthesized and their uncoupling activities of oxidative phosphorylation in mitochondria were examined. The results indicate that the presence of the thiocarbamoyl structure with the potential SH group is a requisite for uncoupling activity. The presence of a C=O group and a hydrophobic aromatic ring significantly increases the uncoupling activity.
D000818:Animals; D055598:Chemical Phenomena; D002621:Chemistry; D006834:Hydrazines / Q000138:chemical synthesis*; D066298:In Vitro Techniques; D008930:Mitochondria, Liver / Q000378:metabolism; D010101:Oxygen Consumption / Q000187:drug effects; D051381:Rats; D013329:Structure-Activity Relationship; D013859:Thiocarbamates / Q000138:chemical synthesis*; D014475:Uncoupling Agents / Q000138:chemical synthesis*
D006834:Hydrazines; D013859:Thiocarbamates; D014475:Uncoupling Agents