Studies on hindered phenols and analogues. 2. 1,3-Benzoxathioles having SRS-A inhibiting activity.
A series of hindered phenolic 1,3-benzoxathioles (7a-l) were prepared and investigated for biological properties. Many compounds had LPO-lowering, antisuperoxide inhibiting, SRS-A inhibiting, and 5-lipoxygenase inhibiting activities. Among them, 5-hydroxy-4,6,7-trimethyl-2-propyl-1,3-benzoxathiole (7d) and 3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiol-2-yl)propanol (7j) were most potent in SRS-A inhibiting and 5-lipoxygenase inhibiting activities, respectively, and were selected for further development as candidate drugs for the treatment of asthma.
Aizawa
Y
Y
Medicinal Chemistry Research Laboratories, Sankyo Company Ltd., Tokyo, Japan.
Kanai
T
T
Hasegawa
K
K
Yamaguchi
T
T
Iizuka
Y
Y
Iwaoka
T
T
Yoshioka
T
T
D000818:Animals; D001249:Asthma / Q000188:drug therapy*; D001583:Benzoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D006168:Guinea Pigs; D015227:Lipid Peroxidation / Q000187:drug effects; D016859:Lipoxygenase Inhibitors; D051379:Mice; D008810:Mice, Inbred C57BL; D013189:SRS-A / Q000037:antagonists & inhibitors*; D013329:Structure-Activity Relationship
D001583:Benzoxazoles; D016859:Lipoxygenase Inhibitors; D013189:SRS-A; C063799:5-hydroxy-4,6,7-trimethyl-2-propyl-1,3-benzoxathiazole; C063800:3-(5-hydroxy-4,6,7-trimethyl-1,3-benzoxathiazol-2-yl)propanol