Benzoic acid 4-((Z)-2-ethoxycarbonyl-3-oxo-hex-1-enylamino)-benzyl ester | 125500-50-7

• 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: Benzoic acid 4-((Z)-2-ethoxycarbonyl-3-oxo-hex-1-enylamino)-benzyl ester
• 英文别名: [4-[(2-ethoxycarbonyl-3-oxohex-1-enyl)amino]phenyl]methyl benzoate
• CAS: 125500-50-7
• 化学式: C₂₃H₂₅NO₅
• 分子量: 395.455
• InChiKey: LZDVGRXXYXZGAD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.27
• 重原子数：
  29.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  81.7
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  Benzoic acid 4-((Z)-2-ethoxycarbonyl-3-oxo-hex-1-enylamino)-benzyl ester 在 三氯氧磷 作用下， 以 1,4-二氧六环 、 二苯醚 为溶剂， 反应 1.0h， 生成 3-butyryl-4-(2-methylphenylamino)-6-benzoyloxymethylquinoline
  参考文献：
  名称：

  Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 4. Identification of an Inhibitor with an Intermediate Duration of Action

  摘要：

  3-Acyl-4-(arylamino)quinolines were previously identified as gastric (H+/K+)-ATPase inhibitors, and clinical efficacy has been demonstrated for compound 3 (SK&F 96067). In the present study the further structure-activity relationship of this series is developed. Only a limited range of substituents are tolerated on the N-aryl ring or the 6- and 7-positions of the quinoline, and although hydroxylated derivatives were identified possessing markedly greater affinity for the enzyme, none of these proved to have adequate potency after oral dosing. In contrast, the 8-position of the quinoline ring proved suitable for a wide variety of substituents, allowing modification of physicochemical properties while retaining primary activity. This led to the identification of compound 4 (SK&F 97574), which combines good oral potency with a somewhat longer duration of action than 3 (though much shorter than covalent inhibitors such as omeprazole). This compound was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00014a026
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 吡啶 、 乙酸酐 作用下， 以 氯仿 为溶剂， 反应 16.5h， 生成 Benzoic acid 4-((Z)-2-ethoxycarbonyl-3-oxo-hex-1-enylamino)-benzyl ester
  参考文献：
  名称：

  Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 4. Identification of an Inhibitor with an Intermediate Duration of Action

  摘要：

  3-Acyl-4-(arylamino)quinolines were previously identified as gastric (H+/K+)-ATPase inhibitors, and clinical efficacy has been demonstrated for compound 3 (SK&F 96067). In the present study the further structure-activity relationship of this series is developed. Only a limited range of substituents are tolerated on the N-aryl ring or the 6- and 7-positions of the quinoline, and although hydroxylated derivatives were identified possessing markedly greater affinity for the enzyme, none of these proved to have adequate potency after oral dosing. In contrast, the 8-position of the quinoline ring proved suitable for a wide variety of substituents, allowing modification of physicochemical properties while retaining primary activity. This led to the identification of compound 4 (SK&F 97574), which combines good oral potency with a somewhat longer duration of action than 3 (though much shorter than covalent inhibitors such as omeprazole). This compound was selected for further development and evaluation in man.

  DOI：

  10.1021/jm00014a026

文献信息

• Compounds substituted quinoline derivatives
  申请人：SmithKline Beecham Intercredit B.V.

  公开号：US05432182A1

  公开（公告）日：1995-07-11

  Substituted 4-aminoquinazoline derivatives which are inhibitors of gastric acid secretion. A compound of the invention are the salts of strong acids of 3-butyryl-4-(2-methylphenylamino)-8-(hydroxymethyl)quinoline.

  该文段的中文翻译如下：替代4-氨基喹唑啉衍生物，是胃酸分泌的抑制剂。该发明的化合物是3-丁酰基-4-(2-甲基苯胺基)-8-(羟甲基)喹啉的强酸盐。
• Substituted 4-aminoquinoline derivatives as gastric acid secretion
  申请人：SmithKline Beckman Intercredit B.V.

  公开号：US05089504A1

  公开（公告）日：1992-02-18

  Substituted 4-aminoquinazoline derivatives of the formula: ##STR1## in which R.sup.1 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, C.sub.1-6 alkoxyC.sub.1-6 alkyl, C.sub.3-6 cycloalkyl, C.sub.3-6 cycloalkylC.sub.1-6 alkyl, phenylC.sub.1-6 alkyl, the phenyl group being optionally substituted; R.sup.2 is hydrogen, C.sub.1-6 alkyl, C.sub.1-6 alkoxy, amino, C.sub.1-6 alkylthio, halogen, cyano, hydroxy, carbamoyl, carboxy, C.sub.1-6 alkanoyl or trifluoromethyl; m is 1 to 3; p is 0 to 4; R.sup.3 is COR.sup.4 ; R.sup.4 is hydroxy, C.sub.1-6 alkoxy, or NR.sup.5 R.sup.6 ; R.sup.5 and R.sup.6 are each hydrogen or C.sub.1-6 alkyl or together with the nitrogen atom to which they are attached form a heterocyclic ring; and R.sup.7 is hydrogen, C.sub.1-6 alkoxy or C.sub.1-6 alkyl; or a salt thereof.

  公式为：##STR1##的4-氨基喹唑啉衍生物，其中R.sup.1是氢、C.sub.1-6烷基、C.sub.1-6烷氧基、C.sub.1-6烷氧基C.sub.1-6烷基、C.sub.3-6环烷基、C.sub.3-6环烷基C.sub.1-6烷基、苯基C.sub.1-6烷基，苯基可选地被取代；R.sup.2是氢、C.sub.1-6烷基、C.sub.1-6烷氧基、氨基、C.sub.1-6烷基硫基、卤素、氰基、羟基、氨甲酰基、羧基、C.sub.1-6烷酰基或三氟甲基；m为1至3；p为0至4；R.sup.3是COR.sup.4；R.sup.4是羟基、C.sub.1-6烷氧基或NR.sup.5R.sup.6；R.sup.5和R.sup.6分别是氢或C.sub.1-6烷基，或与它们连接的氮原子一起形成杂环环；R.sup.7是氢、C.sub.1-6烷氧基或C.sub.1-6烷基；或其盐。