Synthesis and antitumor testing of 3-methenylthiochroman-4-one-1,1-dioxide.
Treatment of thiochroman-4-one-1,1-dioxide (II) with paraformaldehyde and dimethylamine hydrochloride in isopropyl alcohol at reflux afforded directly in 80% yield the dimeric dihydropyran (IV), corresponding to the dimerization of the target compound 3-methenyl-thiochroman-4-one-1,1-dioxide (III). Neither the monomer III nor the expected Mannich base, 3-dimethylaminomethylthiochroman-4-one-1,1-dioxide, were isolated under conditions of the reaction. The monomer III could be prepared in 55% yield by sublimation of the dimer IV at 230-250 degrees; however, redimerization slowly occurred at room temperature. The dimer IV was also prepared by the use of paraformaldehyde and N-methylanilinium trifluoroacetate. The monomer III was found to be marginally active at 10 mg/kg/day versus Ehrlich ascites tumor growth in mice.
D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D001578:Benzopyrans / Q000138:chemical synthesis*; D002286:Carcinoma, Ehrlich Tumor / Q000188:drug therapy; D055598:Chemical Phenomena; D002621:Chemistry; D002839:Chromans / Q000138:chemical synthesis* / Q000494:pharmacology; D008297:Male; D051379:Mice
D000970:Antineoplastic Agents; D001578:Benzopyrans; D002839:Chromans; C035097:3-methenylthiochroman-4-one-1,1-dioxide