1-indoline-2(S)-carboxylic acid | 97975-44-5

• 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: 1-indoline-2(S)-carboxylic acid
• 英文别名: (2S)-1-[(4R)-4-[[(2S)-2,6-bis(phenylmethoxycarbonylamino)hexanoyl]amino]-4-carboxybutanoyl]-2,3-dihydroindole-2-carboxylic acid
• CAS: 97975-44-5
• 化学式: C₃₆H₄₀N₄O₁₀
• 分子量: 688.734
• InChiKey: FGYYEKKMBYTZNA-LXQNXJGFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  50
• 可旋转键数：
  19
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  201
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  1-indoline-2(S)-carboxylic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以71%的产率得到1-(N-L-lysyl-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：

  (S)-5-methoxyindol-2,3-dihydro-2-carboxylic acid hydrochloride 在 palladium on activated charcoal 吡啶 、 N-羟基-5-降冰片烯-2,3-二甲酰亚胺 、 氢气 、 N,N'-二环己基碳二亚胺 作用下， 以 乙醇 为溶剂， 70.0~80.0 ℃ 、101.33 kPa 条件下， 反应 23.5h， 生成 1-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

文献信息

• Tripeptide derivatives
  申请人：Dainippon Pharmaceutical Co., Ltd.

  公开号：EP0244836A2

  公开（公告）日：1987-11-11

  A tripeptide derivative represented by the following formula wherein R1 represents a C1-10 alkyl group, a C4-7 cyclomny or C5-7 cycloalkyl-lower alkyl group, a phenyl or phenyl-lower alkyl group in which the benzene ring may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy, phenyl, methylenedioxy, ethylenedioxy, amino, di(lower alkyl)amino and hydroxy, a naphthyl or naphthyl-lower alkyl group in which the naphthalene ring may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy and hydroxy, a heterocyclic or heterocyclic-lower alkyl group in which the heterocycle is a saturated or unsaturated 5- or 6-membered ring containing a nitrogen, oxygen or sulfur atom as the hetero atom, and may optionally be substituted by a substituent selected from halogen, lower alkyl, lower alkoxy, amino, di(lower alkyl)amino, hydroxy, oxo and saturated 5- or 6-membered nitrogen-containing heterocyclic group, and further may optionally be fused to a benzene ring, or an imidazolylvinyl group; R2 represents a hydrogen atom, a C1-10 alkyl group or a benzyl group; R3 represents a group of the formula in which ( represents a benzene, cyclopentane or cyclohexane ring, R4 represents a hydrogen atom, a C1-10 alkyl group or a benzyl group, p is 0 or 1, q is 1, or 3, and X represents a phenyl group which may optionally be substituted by a substituent selected from halogen, lower alkoxy and hydroxy, a C4-8 cycloalkyl group, or a C5-7 cycloalkyl group which is fused to a benzene, and Y represents a hydrogen atom or a lower alkyl group, or X and Y, together with the nitrogen and carbon atoms to which they are bonded, forms a 5- or 6-membered heterocyle which may contain a nitrogen, oxygen or sulfur atom, W represents a single bond, -O- or -NH-, T represents a single bond, or-S-, and m is 2 or 3, or salts thereof; processes for production thereof; and the use thereof as a medicine, particularly an anti-hypertensive agent.

  下式所代表的三肽衍生物 其中 R1 代表 C1-10 烷基、C4-7 环烷基或 C5-7 环烷基-低级烷基、苯基或苯基-低级烷基，其中苯环可任选被选自卤素、低级烷基、低级烷氧基、苯基、亚甲基二氧基、亚乙基二氧基、氨基、二(低级烷基)氨基和羟基的取代基取代；萘基或萘基-低级烷基，其中萘环可任选被选自卤素、低级烷基、低级烷氧基和羟基的取代基取代；杂环或杂环-低级烷基，其中杂环是饱和或不饱和的 5-或 5-(低级烷基)萘环、杂环或杂环-低级烷基基团，其中杂环是饱和或不饱和的 5 或 6 元环，含氮、氧或硫原子作为杂原子，并可选择被选自卤素、低级烷基、低级烷氧基、低级烷氧基和羟基的取代基取代、低级烷基、低级烷氧基、氨基、二（低级烷基）氨基、羟基、氧代和饱和的 5 或 6 元含氮杂环基团，还可任选与苯环或咪唑乙烯基融合；R2 代表氢原子、C1-10 烷基或苄基； R3 代表如下式的基团 其中 ( 代表苯环、环戊烷环或环己烷环，R4 代表氢原子、C1-10 烷基或苄基，p 为 0 或 1，q 为 1 或 3，X 代表苯基，可任选被选自卤素、低级烷氧基和羟基的取代基取代、一个 C4-8 环烷基，或一个与苯融合的 C5-7 环烷基，Y 代表一个氢原子或一个低级烷基，或 X 和 Y 与它们所键合的氮原子和碳原子一起形成一个 5 或 6 元杂环，该杂环可包含一个氮原子、氧原子或硫原子、 W 代表单键、-O- 或-NH-，T 代表单键、 或-S-，m 为 2 或 3、 或其盐类；其生产工艺；以及其作为药物，特别是抗高血压药物的用途。
• 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.