2-((Z)-2-Ethoxycarbonyl-3-oxo-hex-1-enylamino)-benzoic acid methyl ester | 164861-13-6

• 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: 2-((Z)-2-Ethoxycarbonyl-3-oxo-hex-1-enylamino)-benzoic acid methyl ester
• 英文别名: methyl 2-[(2-ethoxycarbonyl-3-oxohex-1-enyl)amino]benzoate
• CAS: 164861-13-6
• 化学式: C₁₇H₂₁NO₅
• 分子量: 319.357
• InChiKey: JPYWXDGJEWEWRR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  23
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  81.7
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-((Z)-2-Ethoxycarbonyl-3-oxo-hex-1-enylamino)-benzoic acid methyl ester 在 methyl 3-butyryl-4(1H)-quinolone-8-carboxylate 、 乙醚 作用下， 以 二苯醚 为溶剂， 反应 1.0h， 生成 methyl 3-butyryl-4(1H)-quinolone-8-carboxylate
  参考文献：
  名称：

  Substituted 4-aminoquinoline derivatives as gastric acid secretion

  摘要：

  该公式代表的是4-氨基喹唑啉衍生物的替代物，其中R1为氢，C1-6烷基，C1-6烷氧基，C1-6烷氧基C1-6烷基，C3-6环烷基，C3-6环烷基C1-6烷基，苯基C1-6烷基，苯基可以选择性地被取代；R2为氢，C1-6烷基，C1-6烷氧基，氨基，C1-6烷硫基，卤素，氰基，羟基，氨基甲酰基，羧基，C1-6酰基或三氟甲基；m为1至3；p为0至4；R3为COR4；R4为羟基，C1-6烷氧基或NR5R6；R5和R6分别为氢或C1-6烷基，或与它们所连接的氮原子一起形成杂环环；R7为氢，C1-6烷氧基或C1-6烷基；或其盐。

  公开号：

  US05089498A1
• 作为产物：
  描述：

  丁酰乙酸乙酯 在 乙酸酐 作用下， 反应 0.33h， 生成 2-((Z)-2-Ethoxycarbonyl-3-oxo-hex-1-enylamino)-benzoic acid methyl 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

• Substituted 4-aminoquinoline derivatives as gastric acid secretion
  申请人：SmithKline Beckman Intercredit B.V.

  公开号：US05089498A1

  公开（公告）日：1992-02-18

  Substituted 4-aminiquinazoline derivatives of the formula: ##STR1## in which R.sup.1 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 trifluromethyl; 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.

  该公式代表的是4-氨基喹唑啉衍生物的替代物，其中R1为氢，C1-6烷基，C1-6烷氧基，C1-6烷氧基C1-6烷基，C3-6环烷基，C3-6环烷基C1-6烷基，苯基C1-6烷基，苯基可以选择性地被取代；R2为氢，C1-6烷基，C1-6烷氧基，氨基，C1-6烷硫基，卤素，氰基，羟基，氨基甲酰基，羧基，C1-6酰基或三氟甲基；m为1至3；p为0至4；R3为COR4；R4为羟基，C1-6烷氧基或NR5R6；R5和R6分别为氢或C1-6烷基，或与它们所连接的氮原子一起形成杂环环；R7为氢，C1-6烷氧基或C1-6烷基；或其盐。
• Reversible Inhibitors of the Gastric (H+/K+)-ATPase. 4. Identification of an Inhibitor with an Intermediate Duration of Action
  作者：Colin A. Leach、Thomas H. Brown、Robert J. Ife、David J. Keeling、Michael E. Parsons、Colin J. Theobald、Kenneth J. Wiggall

  DOI：10.1021/jm00014a026

  日期：1995.7

  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.