129294-64-0Relevant academic research and scientific papers
An efficient synthesis of 6-substituted aminohexahydro-1H-1,4-diazepines from 2-substituted aminopropenals
Harada, Hiroshi,Morie, Toshiya,Hirokawa, Yoshimi,Kato, Shiro
, p. 2205 - 2212 (2007/10/03)
Swern oxidation of 2-substituted amino-1,3-propanediols 20a - d, 38, 41, and 42 smoothly proceeded to give the oxidative dehydration products, 2-substituted aminopropenals 17a - d, 43, 45 and 46, respectively. Reaction of the intriguing 2-substituted amin
Development of potent serotonin-3 (5-HT3) receptor antagonists. II. Structure-activity relationships of N-(1-benzyl-4-methylhexahydro-1H-1,4- diazepin-6-yl)carboxamides
Harada,Morie,Hirokawa,Terauchi,Fujiwara,Yoshida,Kato
, p. 1912 - 1930 (2007/10/03)
Our studies on 4-amino-5-chloro-2-ethoxybenzamides led to the discovery that the N-(1,4-dimethylhexahydro-1H-1,4-diazepin-6-yl)benzamide 9 and the 1- benzyl-4-methylhexahydro-1H-1,4-diazepine analogue 10 are potent serotonin-3 (5-HT3) receptor antagonists. Structure-activity relationship (SAR) studies on the influence of the aromatic nucleus of 9 and 10 upon inhibition of the von Bezold-Jarisch reflex in rats are described. Heteroaromatic rings such as pyrrole, thiophene, furan, pyridine, pyridaziae, 1,2-benzisoxazole, indole, quinoline, and isoquinoline rings showed weak 5-HT3 receptor antagonistic activity. Within this series, use of the 1H-indazole ring as an aromatic moiety led to a substantial increase of the activity; the 1H- indazolylcarboxamides 54, 57, 97, and 102 showed potent 5-HT3 receptor antagonistic activity. The optimal compound identified via extensive SAR studies was N-(1-benzyl-4-methylhexahydro-1H-1,4-diazepin-6-yl)-1H-indazole- 3-carboxamide (54), whose effect was superior to that of the corresponding benzamide 10 and essentially equipotent to those of ondansetron (1) and granisetron (4).
