title: Antiradiation compounds. 20. 1-Methylquinolinium(and pyridinium)-2-dithioacetic acid derivatives.
abstract: A new class of radiation-protective compounds has been found in the bis(methylthio) and methylthio amino derivatives of 1-methylquinolinium- and 1-methylpyridinium-2-dithioacetic acids. The compounds gave good protection to mice vs. 1000-rad gamma-radiation in ip doses of 10 mg/kg or less, much lower than those required for the aminoalkyl thiols (approximately 150-600 mg/kg). The dithioacetic acid zwitterions were prepared from the base-catalyzed reaction of carbon disulfide with quinaldine and picoline methiodides, and the bis(methylthio) derivatives resulted from reaction with methyl iodide at room temperature. Replacement of one methylthio moiety took place readily on reaction of the bis(methylthio) derivatives with 1 molar equiv of an amine. The best protective activity was found with the methylthio piperidino derivative in both the quinolinium and pyridinium series.
mesh_terms: D000818:Animals; D004305:Dose-Response Relationship, Drug; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D051379:Mice; D011726:Pyridinium Compounds / Q000138:chemical synthesis* / Q000494:pharmacology; D011804:Quinolines / Q000138:chemical synthesis* / Q000494:pharmacology; D011837:Radiation-Protective Agents / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship; D014916:Whole-Body Irradiation
chemical_list: D007202:Indicators and Reagents; D011726:Pyridinium Compounds; D011804:Quinolines; D011837:Radiation-Protective Agents