5-Chloroindoline2-carboxylic acid ethyl ester | 78701-48-1

• 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: 5-Chloroindoline2-carboxylic acid ethyl ester
• 英文别名: 5-chloro-2,3-dihydro-1H-indole-2-carboxylic acid ethyl ester；ethyl 5-chloro-2,3-dihydro-1H-indole-2-carboxylate
• CAS: 78701-48-1
• 化学式: C₁₁H₁₂ClNO₂
• 分子量: 225.675
• InChiKey: OWSUVASONMJJFJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  5-Chloroindoline2-carboxylic acid ethyl ester 在 magnesium turnings 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 methyl 5-chloroindoline-2-carboxylate
  参考文献：
  名称：

  Tripeptidyl peptidase inhibitors

  摘要：

  这项发明涉及一种化合物的公式(I)，以及其作为CCK失活肽酶三肽肽酶(TPP II)的抑制剂的用途。该发明特别涉及治疗进食障碍、肥胖、精神症候群及相关精神障碍。还涉及一种化合物(I)的化妆用途，特别是用于辅助减肥。

  公开号：

  US06335360B1

文献信息

• Angiotensin converting enzyme inhibitors: N-Substituted monocyclic and bicyclic amino acid derivatives
  作者：James L. Stanton、Norbert Gruenfeld、Joseph E. Babiarz、Michael H. Ackerman、Robert C. Friedmann、Andrew M. Yuan、William Macchia

  DOI：10.1021/jm00363a011

  日期：1983.9

  (14a-x),- N-arylalanines (15a,b),-N-cycloalkylglycines (16a-k), and -1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids (17a-d), -1,2,3,4-tetrahydroquinoline-2-carboxylic acids (18a-f), and -indoline-2-carboxylic acids (19a-k) is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound, and the structure--activity relationship for each series is discussed. The

  N-（3-巯基丙酰基）-N-芳基甘氨酸（14a-x），-N-芳基丙氨酸（15a，b），-N-环烷基甘氨酸（16a-k）和-1,2,3,4-的合成描述了四氢异喹啉-3-羧酸（17a-d），-1,2,3,4-四氢喹啉-2-羧酸（18a-f）和-二氢吲哚-2-羧酸（19a-k）。报道了每种化合物对血管紧张素转化酶（ACE）的体外抑制作用，并讨论了每个系列的结构-活性关系。讨论了ACE的体内抑制作用和各系列代表性化合物的降压作用。最有效的化合物19d的体外ACE IC50为2.6 X 10（-9）M，并且以10 mg / kg po的剂量在85 mm的自发性高血压大鼠中降低了血压。
• 1,1'-[Dithiobis(2-alkyl-1-oxo-3,1-propanediyl)]-bis[2,3-dihydro-1H-indole
  申请人：American Home Products Corporation

  公开号：US04396773A1

  公开（公告）日：1983-08-02

  Disclosed herein are N-(3-mercapto-2-alkyl-1-oxopropyl)-2,3-dihydro-1H-indole-2-carboxylic acids and derivatives thereof which act as inhibitors of angiotensin converting enzyme and as anti-hypertensive agents. Derivatives include those in which the 3-mercapto group is substituted with phosphate derivatives or is replaced by a variously substituted amino group. 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; R.sub.4 is -SH, ##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.

  本文揭示了N-(3-巯基-2-烷基-1-氧代丙基)-2,3-二氢-1H-吲哚-2-羧酸及其衍生物，其作为抑制血管紧张素转化酶和降压药物的作用。衍生物包括那些其中3-巯基团被磷酸衍生物取代或被各种取代的氨基团替换的化合物。发明的化合物（不包括已披露的中间体）具有以下通式： 其中：n为1或0；R.sub.1为氢、低烷基、芳基或芳基烷基；R.sub.2为氢或低烷基；R.sub.3为氢、低烷基或芳酰基；R.sub.5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；R.sub.4为-SH、 其中L为O、NR.sub.7或S（其中R.sub.7为氢或低烷基）；M为R.sub.8、OR.sub.8、SR.sub.8或NR.sub.9R.sub.10（其中R.sub.8为氢、低烷基、芳基或芳基烷基；R.sub.9和R.sub.10分别为氢、低烷基或芳基）；A为O、NR.sub.13或S；R.sub.11和R.sub.12分别为氢、烷基、芳基烷基或芳基；R.sub.13为氢或低烷基；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：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。
• 1H,5H-[1,4]Thiazepino[4,3-a]indole-1,5-diones
  申请人：American Home Products Corporation

  公开号：US04303583A1

  公开（公告）日：1981-12-01

  Disclosed herein are N-(3-mercapto-2-alkyl-1-oxopropyl)-2,3-dihydro-1H-indole-2-carboxylic acids and derivatives thereof which act as inhibitors of angiotensin converting enzyme and as anti-hypertensive agents. Derivatives include those in which the 3-mercapto group is substituted with phosphate derivatives or is replaced by a variously substituted amino group. 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; R.sub.4 is --SH, ##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, 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N-(3-巯基-2-烷基-1-氧代丙基)-2,3-二氢-1H-吲哚-2-羧酸及其衍生物，其作为抑制肾素转化酶和降压药物。衍生物包括那些其中3-巯基基团被磷酸酯衍生物取代或被各种取代的氨基团替换的化合物。发明的化合物（不包括披露的中间体）具有以下一般式：##STR1## 其中：n为1或0；R.sub.1为氢、低烷基、芳基或芳基烷基；R.sub.2为氢或低烷基；R.sub.3为氢、低烷基或芳酰基；R.sub.5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；R.sub.4为--SH，##STR2## 其中L为O、NR.sub.7或S（其中R.sub.7为氢或低烷基）；M为R.sub.8、OR.sub.8或NR.sub.9 R.sub.10（其中R.sub.8为氢、低烷基、芳基或芳基烷基；R.sub.9和R.sub.10分别为氢、低烷基或芳基）；A为O、NR.sub.13或S；R.sub.11和R.sub.12分别为氢、烷基、芳基烷基或芳基；R.sub.13为氢或低烷基；m为0、1、2或3；R.sub.20为氢或芳基；R.sub.21为羟基或低烷氧基；或其药用盐。
• [EN] BENZOPYRANYL HETEROCYCLE DERIVATIVES, PROCESS FOR PREPARATION THEREOF, AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM<br/>[FR] DERIVES HETEROCYCLIQUES DE BENZOPYRANYLE, METHODE DE PREPARATION DESDITS DERIVES ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT
  申请人：DONGBU HANNONG CHEMICAL CO LTD

  公开号：WO2002030925A1

  公开（公告）日：2002-04-18

  The present invention relates to novel benzopyranyl heterocycle derivatives, process for preparation thereof and pharmaceutical use of the benzopyranyl heterocycle derivatives. The benzopyranyl heterocycle derivatives of the present invention can be used for protecting heart, brain, retina and neuronal cell from 'ischemia-reperfusion' injury, treatment for diseases related to it and suppressing lipid peroxidation.

  本发明涉及新型苯并吡喃杂环衍生物、其制备方法和苯并吡喃杂环衍生物的药用。本发明的苯并吡喃杂环衍生物可用于保护心脏、大脑、视网膜和神经细胞免受“缺血再灌注”损伤，治疗与之相关的疾病以及抑制脂质过氧化反应。