[Synthesis of 3-[4-[(3-alkylamino-2-hydroxy)propoxy]phenyl (benzyl)]-substituted 4(3H)-quinazolines as antimyocardial ischemic agents].
In order to search for effective antimyocardial ischemic agents, fourteen new 3-[4-[(3-alkylamino-2-hydroxy)propoxy]phenyl(benzyl)]-substituted 4(3H)-quinazolinones (II) were synthesized. Substituted o-aminobenzoic acids used as the starting materials were allowed to react with acetic anhydride and then p-amino-phenol (method A), or with N-(4-hydroxyphenyl)formamide (method B), or with thionyl chloride and then N-(4-hydroxybenzyl)formamide (method C) to form 3-[(4-hydroxyphenyl(benzyl)]-substituted 4(3H)-quinazolinones (III). The intermediate III reacted with epichlorohydrin to form the epoxides (IV). The reaction of IV with an excess of isopropylamine or tert-butylamine in boiling chloroform gave the desired products. Of all the compounds synthesized, compounds II3-5 and II13 were found to increase the tolerance of mice to hypoxia. Further evaluation is in progress.
Cai
Y C
YC
Institute of Pharmacology and Toxicology, Academy of Military Medical Sciences, Beijing.
Dong
Y M
YM
D000319:Adrenergic beta-Antagonists / Q000138:chemical synthesis*; D000588:Amines / Q000138:chemical synthesis / Q000494:pharmacology; D000818:Animals; D001593:Benzyl Compounds / Q000138:chemical synthesis / Q000494:pharmacology; D000860:Hypoxia / Q000188:drug therapy; D051379:Mice; D011799:Quinazolines / Q000138:chemical synthesis* / Q000494:pharmacology
D000319:Adrenergic beta-Antagonists; D000588:Amines; D001593:Benzyl Compounds; D011799:Quinazolines