4-{2-[(4-Amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-ylmethyl}-benzoic acid methyl ester | 131322-30-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-{2-[(4-Amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-ylmethyl}-benzoic acid methyl ester
• 英文别名: Methyl 4-[[2-[[(4-amino-5-chloro-2-ethoxybenzoyl)amino]methyl]morpholin-4-yl]methyl]benzoate
• CAS: 131322-30-0
• 化学式: C₂₃H₂₈ClN₃O₅
• 分子量: 461.945
• InChiKey: OLLRLDTTWKPNEF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  103
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-{2-[(4-Amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-ylmethyl}-benzoic acid methyl ester 在 sodium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以93%的产率得到4-amino-N-{[4-(4-carboxybenzyl)-2-morpholinyl]methyl}-5-chloro-2-ethoxybenzamide
  参考文献：
  名称：

  Novel benzamides as selective and potent gastrokinetic agents. 2. Synthesis and structure-activity relationships of 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide citrate (AS-4370) and related compounds

  摘要：

  The title compounds (19-55) with a 4-substituted 2-(aminomethyl) morpholine group were prepared and evaluated for the gastrokinetic activity by determining their effect on gastric emptying of phenol red semisolid meal in rats. Introduction of chloro, fluoro, and trifluoromethyl groups to the benzyl group of the parent compounds 1a and 1b enhanced the activity. Among compounds tested, 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]?? methyl]benzamide (23b) showed the most potent gastic emptying activity (effects on phenol red semisolid meal in rats and mice, and on resin pellets solid meal in rats). The gastrokinetic activity of 23b citrate (AS-4370) compared very favorably with that of cisapride and was higher than that of metoclopramide. In contrast to metoclopramide and cisapride, AS-4370 was free from dopamine D2 receptor antagonistic activity in both in vitro ([H-3]spiperone binding) and in vivo (apomorphine-induced emesis in dogs) tests.

  DOI：

  10.1021/jm00106a023
• 作为产物：
  描述：

  4-乙酰氨基-5-氯-2-乙氧基苯甲酸甲酯 在 sodium hydroxide 、 水 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 9.0h， 生成 4-{2-[(4-Amino-5-chloro-2-ethoxy-benzoylamino)-methyl]-morpholin-4-ylmethyl}-benzoic acid methyl ester
  参考文献：
  名称：

  Novel benzamides as selective and potent gastrokinetic agents. 2. Synthesis and structure-activity relationships of 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]methyl]benzamide citrate (AS-4370) and related compounds

  摘要：

  The title compounds (19-55) with a 4-substituted 2-(aminomethyl) morpholine group were prepared and evaluated for the gastrokinetic activity by determining their effect on gastric emptying of phenol red semisolid meal in rats. Introduction of chloro, fluoro, and trifluoromethyl groups to the benzyl group of the parent compounds 1a and 1b enhanced the activity. Among compounds tested, 4-amino-5-chloro-2-ethoxy-N-[[4-(4-fluorobenzyl)-2-morpholinyl]?? methyl]benzamide (23b) showed the most potent gastic emptying activity (effects on phenol red semisolid meal in rats and mice, and on resin pellets solid meal in rats). The gastrokinetic activity of 23b citrate (AS-4370) compared very favorably with that of cisapride and was higher than that of metoclopramide. In contrast to metoclopramide and cisapride, AS-4370 was free from dopamine D2 receptor antagonistic activity in both in vitro ([H-3]spiperone binding) and in vivo (apomorphine-induced emesis in dogs) tests.

  DOI：

  10.1021/jm00106a023

文献信息

• KATO, SHIRO;MORIE, TOSHIYA;KON, TATSUYA;YOSHIDA, NAOYUKI;KARASAWA, TADAHI+, J. MED. CHEM., 34,(1991) N, C. 616-624
  作者：KATO, SHIRO、MORIE, TOSHIYA、KON, TATSUYA、YOSHIDA, NAOYUKI、KARASAWA, TADAHI+

  DOI：——

  日期：——