(S)-1-[(S)-2-amino-1-oxopropyl]-2,3-dihydro-1H-indole-2-carboxylic acid | 83234-70-2

• 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: (S)-1-[(S)-2-amino-1-oxopropyl]-2,3-dihydro-1H-indole-2-carboxylic acid
• 英文别名: (2S)-1-[(2S)-2-aminopropanoyl]-2,3-dihydroindole-2-carboxylic acid
• CAS: 83234-70-2
• 化学式: C₁₂H₁₄N₂O₃
• mdl: MFCD13214642
• 分子量: 234.255
• InChiKey: NXKLFGRJFARTBP-XVKPBYJWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.333
• 拓扑面积：
  83.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (S)-1-[(S)-2-amino-1-oxopropyl]-2,3-dihydro-1H-indole-2-carboxylic acid 、 2-氧代-4-苯基丁酸乙酯 生成 WY-44655 free acid
  参考文献：
  名称：

  KIM, D. H.;MCCAULLY, R. J.

  摘要：

  DOI：
• 作为产物：
  描述：

  (S)-2,3-Dihydro-1-[(S)-2-(1,3-dihydro-1,3-dioxo-2H-isoindol-2-yl)-1-oxopropyl]-1H-indole-2-carboxylic acid 生成 (S)-1-[(S)-2-amino-1-oxopropyl]-2,3-dihydro-1H-indole-2-carboxylic acid
  参考文献：
  名称：

  KIM, D. H.;MCCAULLY, R. J.

  摘要：

  DOI：

文献信息

• N-(2-Substituted-1-oxoalkyl)-2,3-dihydro-1H-indole-2-carboxylic acid
  申请人：American Home Products Corporation

  公开号：US04350633A1

  公开（公告）日：1982-09-21

  Disclosed herein are 2,3-dihydro-1H-indole-2-carboxylic acids substituted on the nitrogen with 3-mercapto-2-alkyl-1-oxoalkyl, 3-phosphoryl-2-alkyl-1-oxopropyl, or 2-amino-2-alkyl-1-oxoalkyl derivatives which act as inhibitors of angiotensin converting enzyme and as antihypertensive agents. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0; R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen, lower alkyl or aroyl; R.sub.5 is hydroxy, amino, or lower alkoxy; X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen; Y is hydrogen, lower alkyl, or aryl; Y is hydrogen, lower alkyl, or aryl; R.sub.4 is ##STR2## wherein: L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl); M is R.sub.8, OR.sub.8, SR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.10 are, independently, hydrogen, lower alkyl, or aryl); A is O, NR.sub.13 or S; R.sub.11 and R.sub.12 are, independently, hydrogen, alkyl, aralkyl or aryl; R.sub.13 is hydrogen or lower alkyl; m is 0, 1, 2, or 3; R.sub.20 is hydrogen or aryl; and R.sub.21 is hydroxy or lower alkoxy; or pharmaceutically acceptable salts thereof.

  本文披露了在氮上用3-巯基-2-烷基-1-氧代烷基、3-磷酰基-2-烷基-1-氧代丙基或2-氨基-2-烷基-1-氧代烷基衍生物取代的2,3-二氢-1H-吲哚-2-羧酸，其作为抑制肾素转化酶和降压剂。发明的化合物（不包括披露的中间体）具有以下通用式：其中：n为1或0；R1为氢、低烷基、芳基或芳基烷基；R2为氢或低烷基；R3为氢、低烷基或芳酰基；R5为羟基、氨基或低烷氧基；X为氢、羟基、低烷基、低烷氧基或卤素；Y为氢、低烷基或芳基；R4为其中：L为O、NR7或S（其中R7为氢或低烷基）；M为R8、OR8、SR8或NR9R10（其中R8为氢、低烷基、芳基或芳基烷基；R9和R10分别为氢、低烷基或芳基）；A为O、NR13或S；R11和R12分别为氢、烷基、芳基烷基或芳基；R13为氢或低烷基；m为0、1、2或3；R20为氢或芳基；R21为羟基或低烷氧基；或其药用盐。
• N-[2-Substituted-1-oxoalkyl]-2,3-dihydro-1H-indole-2-carboxylic acid
  申请人：American Home Products Corporation

  公开号：US04454292A1

  公开（公告）日：1984-06-12

  Disclosed herein are 2,3-dihydro-1H-indole-2-carboxylic acids substitued on the nitrogen with 3-mercapto-2-alkyl-1-oxoalkyl, 3-phosphoryl-2-alkyl-1-oxopropyl, or 2-amino-2-alkyl-1-oxoalkyl derivatives which act as inhibitors of angiotensin converting enzyme and as antihypertensive agents. The compounds of the invention (excluding disclosed intermediates) have the general formula: ##STR1## wherein: n is 1 or 0; R.sub.1 is hydrogen, lower alkyl, aryl or aralkyl; R.sub.2 is hydrogen or lower alkyl; R.sub.3 is hydrogen, lower alkyl or aroyl; R.sub.5 is hydroxy, amino, or lower alkoxy; X is hydrogen, hydroxy, lower alkyl, lower alkoxy, or halogen; Y is hydrogen, lower alkyl, or aryl; Y is hydrogen, lower alkyl, or aryl; R.sub.4 is ##STR2## wherein: L is O, NR.sub.7 or S (where R.sub.7 is hydrogen or lower alkyl); M is R.sub.8, OR.sub.8, SR.sub.8, or NR.sub.9 R.sub.10 (where R.sub.8 is hydrogen, lower alkyl, aryl, or aralkyl; and R.sub.9 and R.sub.10 are, independently, hydrogen, lower alkyl, or aryl); A is O, NR.sub.13 or S; R.sub.11 and R.sub.12 are, independently, hydrogen, alkyl, aralkylor aryl; R.sub.13 is hydrogen or lower alkyl; m is 0, 1, 2, or 3; R.sub.20 is hydrogen or aryl; and R.sub.21 is hydroxy or lower alkoxy; or pharmaceutically acceptable salts thereof. Claimed compounds are intermediates of the formula: ##STR3## wherein R.sub.15 is hydrogen or lower alkyl.

  本文披露了一种以3-巯基-2-烷基-1-氧代烷基、3-磷酸-2-烷基-1-氧代丙基或2-氨基-2-烷基-1-氧代烷基衍生物取代氮的2,3-二氢-1H-吲哚-2-羧酸，其作为血管紧张素转换酶抑制剂和降压剂。该发明化合物（不包括披露的中间体）的一般式如下：##STR1## 其中：n为1或0；R.sub.1为氢、低级烷基、芳基或芳烷基；R.sub.2为氢或低级烷基；R.sub.3为氢、低级烷基或芳酰基；R.sub.5为羟基、氨基或低级烷氧基；X为氢、羟基、低级烷基、低级烷氧基或卤素；Y为氢、低级烷基或芳基；R.sub.4为##STR2## 其中：L为O、NR.sub.7或S（其中R.sub.7为氢或低级烷基）；M为R.sub.8、OR.sub.8、SR.sub.8或NR.sub.9 R.sub.10（其中R.sub.8为氢、低级烷基、芳基或芳烷基；R.sub.9和R.sub.10独立地为氢、低级烷基或芳基）；A为O、NR.sub.13或S；R.sub.11和R.sub.12独立地为氢、烷基、芳烷基或芳基；R.sub.13为氢或低级烷基；m为0、1、2或3；R.sub.20为氢或芳基；R.sub.21为羟基或低级烷氧基；或其药学上可接受的盐。所述的化合物是以下中间体：##STR3## 其中R.sub.15为氢或低级烷基。
• Design and synthesis of α,β-unsaturated carbonyl compounds as potential ACE inhibitors
  作者：H Choo

  DOI：10.1016/s0223-5234(00)00158-6

  日期：2000.6

  The alpha,beta-unsaturated amide that is incorporated into the basic structural frame of a simple substrate molecule of angiotensin converting enzyme was found to serve as a Michael acceptor for the catalytic carboxylate of Glu-127, inhibiting the enzyme irreversibly. (C) 2000 Editions scientifiques et medicales Elsevier SAS.
• KIM, DONG, H.;MCCAULLY, R. J.
  作者：KIM, DONG, H.、MCCAULLY, R. J.

  DOI：——

  日期：——
• KIM, D. H.;MCCAULLY, R. J.
  作者：KIM, D. H.、MCCAULLY, R. J.

  DOI：——

  日期：——