Synthesis and central nervous system activity of quinazolones related to 2-methyl-3-(o-tolyl)-4(3H)-quinazolone (methaqualone).
A number of derivatives of 2-methyl-3-(o-tolyl)-4(3H)-quinazolone bearing new substituents on the 2-methyl group have been synthesized. It was established that most substitutions at this position reduce or remove the CNS depressant activity of methaqualone. From the series prepared only the 2-fluoromethyl derivative or certain isothiouronium salts, which could be hydrolyzed in vivo to the 2-mercaptomethyl derivative, showed activity of the same magnitude as methaqualone.
D000818:Animals; D000927:Anticonvulsants / Q000138:chemical synthesis; D002490:Central Nervous System / Q000187:drug effects*; D003864:Depression, Chemical; D008297:Male; D008702:Methaqualone / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D051379:Mice; D004856:Postural Balance / Q000187:drug effects; D011809:Quinones / Q000037:antagonists & inhibitors; D013329:Structure-Activity Relationship
D000927:Anticonvulsants; D011809:Quinones; D008702:Methaqualone