(S)-5-methoxyindol-2,3-dihydro-2-carboxylic acid hydrochloride | 82923-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (S)-5-methoxyindol-2,3-dihydro-2-carboxylic acid hydrochloride
• 英文别名: (S)-indoline-2-carboxylic acid hydrochloride；indoline-2(S)-carboxylic acid hydrochloride；(S)-2,3-dihydro-1H-indole-2-carboxylic acid hydrochloride；indoline-2S-carboxylic acid hydrochloride；(2S)-2,3-dihydro-1H-indole-2-carboxylic acid;hydrochloride
• CAS: 82923-76-0
• 化学式: C₉H₉NO₂*ClH
• 分子量: 199.637
• InChiKey: MXDFDHKSOLTAHJ-QRPNPIFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.53
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  49.3
• 氢给体数：
  3
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-5-methoxyindol-2,3-dihydro-2-carboxylic acid hydrochloride 在 palladium on activated charcoal 吡啶 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 80.0 ℃ 、101.33 kPa 条件下， 反应 36.0h， 生成 1-(N-acetyl-γ-D-glutamyl)indoline-2(S)-carboxylic acid
  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：

  吲哚-2-羧酸 在 platinum(IV) oxide 盐酸 、 氢气 、 三乙胺 作用下， 100.0 ℃ 、101.33 kPa 条件下， 反应 2.0h， 生成 (S)-5-methoxyindol-2,3-dihydro-2-carboxylic acid hydrochloride
  参考文献：
  名称：

  血管紧张素转化酶抑制剂：N-取代的单环和双环氨基酸衍生物。

  摘要：

  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。

  DOI：

  10.1021/jm00363a011

文献信息

• [EN] COSMETIC USES AND METHODS FOR INDOLINE GRANZYME B INHIBITOR COMPOSITIONS<br/>[FR] UTILISATIONS ET PROCÉDÉS COSMÉTIQUES POUR DES COMPOSITIONS D'INHIBITEUR D'INDOLINE GRANZYME B
  申请人：VIDA THERAPEUTICS INC

  公开号：WO2014153667A1

  公开（公告）日：2014-10-02

  Cosmetic uses and methods for indoline granzyme B inhibitor compounds in compositions with a cosmetically acceptable carrier. Uses and methods for treating, reducing or inhibiting the appearance of ageing in the skin are provided. Also provided are compositions and formulation for cosmetic uses and methods of maintaining a youthful appearance, reducing an appearance of ageing, inhibiting an appearance of ageing, reducing a rate of an appearance of ageing, reducing a skin inelasticity, reducing a rate of increasing skin inelasticity, maintaining a skin elasticity, and increasing the density of hair follicles of a skin of a subjecl. The uses and methods comprise applying/administering an indoline granzyme B inhibitor to a skin, or a portion of a skin of the subject.

  使用和方法用于在与化妆品可接受载体混合的化合物中使用吲哚啶颗粒酶B抑制剂。提供了用于治疗、减少或抑制皮肤衰老的用途和方法。还提供了用于化妆品用途的组合物和配方，以及保持年轻外观、减少衰老外观、抑制衰老外观、减少衰老外观速率、减少皮肤无弹性、减少增加皮肤无弹性速率、保持皮肤弹性和增加皮肤毛囊密度的方法。这些用途和方法包括将吲哚啶颗粒酶B抑制剂涂抹/施用于皮肤或受试者皮肤的部分。
• (Substituted)acyl dipeptidyl inhibitors of the ICE/ced-3 family of cysteine proteases
  申请人：Idun Pharmaceuticals, Inc.

  公开号：US20030232788A1

  公开（公告）日：2003-12-18

  This invention is directed to novel (substituted)acyl dipeptidyl ICE/ced-3 family inhibitor compounds. The invention is also directed to pharmaceutical compositions containing these compounds, as well as the use of such compositions in the treatment of patients suffering inflammatory, autoimmune and neurodegenerative diseases, for the prevention of ischemic injury, and for the preservation of organs that are to undergo a transplantation procedure.

  这项发明涉及新型（取代）酰基二肽酶ICE/ced-3家族抑制剂化合物。该发明还涉及含有这些化合物的药物组合物，以及将这些组合物用于治疗患有炎症、自身免疫和神经退行性疾病的患者，预防缺血性损伤，并保护即将进行移植手术的器官。
• PYRROLOBENZODIAZEPINES AND CONJUGATES THEREOF
  申请人：Mersana Therapeutics, Inc.

  公开号：US20170369453A1

  公开（公告）日：2017-12-28

  The present disclosure relates generally to derivatives of pyrrolobenzodiazepines and antibody-drug conjugates thereof and to methods of using these conjugates as therapeutics and/or diagnostics.

  本公开涉及吡咯苯并二氮杂苯并二氮杂二环己烯衍生物及其抗体药物结合物，以及使用这些结合物作为治疗和/或诊断的方法。
• 1-Carboxyalkanoylindoline-2-carboxylic acids
  申请人：Ciba-Geigy Corporation

  公开号：US04479963A1

  公开（公告）日：1984-10-30

  1-Carboxy-(alkanoyl or aralkanoyl)-indoline-2-carboxylic acids, e.g., those of the formula ##STR1## R=H, alkyl, alkoxy, halogeno or CF.sub.3 ; R'=H or R-phenyl; m=0 or 1; p,q=0 to 2; and derivatives thereof, are antihypertensive and cardioactive agents.

  1-羧基-(烷酰基或芳基烷酰基)-吲哚-2-羧酸，例如，具有以下结构式的化合物 ##STR1## R=H，烷基，烷氧基，卤素或CF.sub.3；R'=H或R-苯基；m=0或1；p，q=0至2；及其衍生物，是抗高血压和心脏活性药物。
• Process for the preparation of enantiomerically enriched indoline-2-carboxylic acid
  申请人：DSM IP Assets B.V.

  公开号：EP1676838A1

  公开（公告）日：2006-07-05

  The present invention relates to a process for the preparation of an enantiomerically enriched optionally substituted indoline-2-carboxylic acid or a salt thereof, said process comprising subjecting an enantiomerically enriched chiral 2-amino-3-(2-X-substituted aryl)-propionic acid or 2-yl-substituted-amino -3-(2-X-substituted aryl)-propionic acid or a salt thereof, wherein X is a leaving group, to cyclisation, preferably at a temperature of below about 140°C, and in case of the yl-substituted compound, removing said yl-substituent by hydrolysis either prior to or after said cyclisation.

  本发明涉及一种制备对映体富集的可选择取代的吲哚啉-2-羧酸或其盐的过程，该过程包括将对映体富集的手性2-氨基-3-(2-X-取代芳基)-丙酸或2-基取代氨基-3-(2-X-取代芳基)-丙酸或其盐，其中X是一个离去基团，经过环化，优选在约140°C以下的温度下进行，对于基取代化合物，可在环化之前或之后通过水解去除该基取代基团。