indoline-2S-carboxylic acid-3-pyridylmethylester | 97975-29-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: indoline-2S-carboxylic acid-3-pyridylmethylester
• 英文别名: pyridin-3-ylmethyl (2S)-2,3-dihydro-1H-indole-2-carboxylate
• CAS: 97975-29-6
• 化学式: C₁₅H₁₄N₂O₂
• 分子量: 254.288
• InChiKey: XPUQOPJJDHNWJA-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  [(3R)-四氢-2,6-二氧代-2H-吡喃-3-基]-氨基甲酸苯基甲基 、 indoline-2S-carboxylic acid-3-pyridylmethylester 以 四氢呋喃 为溶剂， 反应 18.0h， 以25%的产率得到3-pyridylmethyl 1-(N-carbobenzoxy-γ-D-glutamyl)indoline-2(S)-carboxylate
  参考文献：
  名称：

  Angiotensin converting enzyme inhibitors: N-substituted D-glutamic acid .gamma.-dipeptides

  摘要：

  The preparation of two series of N-carbobenzoxy-gamma-D-glutamyl secondary 2S amino acids and (N-substituted gamma-D-glutamyl)indoline-2(S)-carboxylic acid dipeptides is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound, and the structure-activity relationship is discussed. Oral and iv inhibition of AI pressor response in vivo of selected compounds in Table II is also discussed. The most potent compounds in vitro, 3 and 6a, had an ACE IC50 of 7 and 2.7 X 10(-9) M, respectively.

  DOI：

  10.1021/jm00149a011
• 作为产物：
  描述：

  indoline-2S-carboxylic acid-3-dimethylaminopropyl ester 、 N-苄氧羰基-L-谷氨酸酐 以 二氯甲烷 为溶剂， 生成 indoline-2S-carboxylic acid-3-pyridylmethylester
  参考文献：
  名称：

  Gamma-r-glutamoyl derivatives

  摘要：

  该化合物的化学式为##STR1##其中R.sub.1和R.sub.6分别表示羟基、C.sub.1-C.sub.4-烷氧基、取代的C.sub.1-C.sub.4-烷氧基、氨基或取代的氨基，R.sub.2表示氢、C.sub.1-C.sub.4-烷基或C.sub.2-C.sub.4-烯基，R.sub.3表示环状C.sub.3-C.sub.6-烷基、苯基、被C.sub.1-C.sub.4-烷基、卤素、硝基或C.sub.1-C.sub.4-烷氧基取代的苯基，或者与苯环融合的环状C.sub.3-C.sub.6-烷基，或者R.sub.2和R.sub.3相连，并与相邻的--CH基团和相邻的N原子一起形成饱和或部分饱和的、单环、五元或六元杂环基团，或形成含有五个或六个原子的饱和或部分饱和的双环杂环基团，R.sub.4表示氢或C.sub.1-C.sub.4-烷基，R.sub.5表示酰基基团，可用作降压和心脏活性药物。本发明还涉及制备式I化合物的方法和制药组合物。

  公开号：

  US04678800A1

文献信息

• US4678800A
  申请人：——

  公开号：US4678800A

  公开（公告）日：1987-07-07
• Angiotensin converting enzyme inhibitors: N-substituted D-glutamic acid .gamma.-dipeptides
  作者：Gary M. Ksander、Andrew M. Yuan、Clive G. Diefenbacher、James L. Stanton

  DOI：10.1021/jm00149a011

  日期：1985.11

  The preparation of two series of N-carbobenzoxy-gamma-D-glutamyl secondary 2S amino acids and (N-substituted gamma-D-glutamyl)indoline-2(S)-carboxylic acid dipeptides is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound, and the structure-activity relationship is discussed. Oral and iv inhibition of AI pressor response in vivo of selected compounds in Table II is also discussed. The most potent compounds in vitro, 3 and 6a, had an ACE IC50 of 7 and 2.7 X 10(-9) M, respectively.
• Gamma-r-glutamoyl derivatives
  申请人：Ciba-Geigy Corporation

  公开号：US04678800A1

  公开（公告）日：1987-07-07

  A compound of the formula ##STR1## wherein R.sub.1 and R.sub.6 independently represent hydroxy, C.sub.1 -C.sub.4 -alkoxy, substituted C.sub.1 -C.sub.4 - alkoxy, amino, or substituted amino, R.sub.2 represents hydrogen, C.sub.1 -C.sub.4 -alkyl, or C.sub.2 -C.sub.4 -alkenyl, R.sub.3 represents cyclo-C.sub.3 -C.sub.6 -alkyl, phenyl, phenyl substituted by C.sub.1 -C.sub.4 -alkyl, halogen, nitro, or C.sub.1 -C.sub.4 -alkoxy, or cyclo-C.sub.3 -C.sub.6 -alkyl fused with benzene, or wherein R.sub.2 and R.sub.3 are connected and together with the adjacent --CH-group and the adjacent N-atom form a saturated or partially saturated, monocyclic, five- or six-membered heterocyclic group or form a saturated or partially saturated, bicyclic heterocyclic group containing five or six atoms per ring, R.sub.4 represents hydrogen or C.sub.1 -C.sub.4 -alkyl, and R.sub.5 represents an acyl group, are useful as antihypertensive and cardioactive agents. The invention also relates to processes for preparing the compounds of the formula I and to pharmaceutical compositions.

  该化合物的化学式为##STR1##其中R.sub.1和R.sub.6分别表示羟基、C.sub.1-C.sub.4-烷氧基、取代的C.sub.1-C.sub.4-烷氧基、氨基或取代的氨基，R.sub.2表示氢、C.sub.1-C.sub.4-烷基或C.sub.2-C.sub.4-烯基，R.sub.3表示环状C.sub.3-C.sub.6-烷基、苯基、被C.sub.1-C.sub.4-烷基、卤素、硝基或C.sub.1-C.sub.4-烷氧基取代的苯基，或者与苯环融合的环状C.sub.3-C.sub.6-烷基，或者R.sub.2和R.sub.3相连，并与相邻的--CH基团和相邻的N原子一起形成饱和或部分饱和的、单环、五元或六元杂环基团，或形成含有五个或六个原子的饱和或部分饱和的双环杂环基团，R.sub.4表示氢或C.sub.1-C.sub.4-烷基，R.sub.5表示酰基基团，可用作降压和心脏活性药物。本发明还涉及制备式I化合物的方法和制药组合物。