ethyl 3-acetylamino-2-(1-ethoxycarbonyl-5-fluoroindol-3-yl)-propanoate | 73139-87-4

• 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: ethyl 3-acetylamino-2-(1-ethoxycarbonyl-5-fluoroindol-3-yl)-propanoate
• 英文别名: Ethyl 3-(3-acetamido-1-ethoxy-1-oxopropan-2-yl)-5-fluoroindole-1-carboxylate
• CAS: 73139-87-4
• 化学式: C₁₈H₂₁FN₂O₅
• 分子量: 364.374
• InChiKey: ALIUXDQXTXWQEV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  86.6
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-acetylamino-2-(1-ethoxycarbonyl-5-fluoroindol-3-yl)-propanoate 在 sodium hydroxide 、 氯化亚砜 作用下， 反应 26.0h， 生成 3-Amino-2-(5-fluoro-1H-indol-3-yl)-propionic acid methyl ester
  参考文献：
  名称：

  Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers

  摘要：

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.

  DOI：

  10.1021/jm00348a022
• 作为产物：
  描述：

  ethyl 2-cyano-2-(1-ethoxycarbonyl-5-fluoroindol-3-yl)-acetate 以 乙酸酐 为溶剂， 以9 g (46%)的产率得到ethyl 3-acetylamino-2-(1-ethoxycarbonyl-5-fluoroindol-3-yl)-propanoate
  参考文献：
  名称：

  3-Amino or amido-2-(1H-indol-3-yl) propanoic acid derivatives

  摘要：

  本发明涉及一种以结构式表示的化合物：##STR1## 其中，上述式中限定的各种化合物中：R为H，CH.sub.3或CH.sub.2 CH.sub.3，R'为H或##STR2## X为H，F或OCH.sub.3，Y为H或Cl，Z为H或##STR3## 作为抗高血压药物，这些化合物具有治疗作用。

  公开号：

  US04283410A1

文献信息

• Synthesis of 3-Amino-2-(3-indolyl)propanol and Propanoate Derivatives and Preliminary Cardiovascular Evaluation in Rats
  作者：Victor Pérez-Alvarez、Martha S Morales-Ríos、Enrique Hong、Pedro Joseph-Nathan

  DOI：10.1111/j.2042-7158.1997.tb06789.x

  日期：2011.4.12

  A series of tryptamine analogues has been prepared and tested for their 5-HT1 receptor agonist properties.

  The incorporation of an alkoxy group at the C-5 position of the indole nucleus resulted in a short-lived and dose-dependent immediate antihypertensive and bradycardic response in anaesthetized spontaneously hypertensive rats (SHR). In addition, a carbomethoxy function at the β-position of the side-chain of the tryptamines significantly increased the mean resting arterial blood pressure (MAP) in pithed rats and also produced contraction of the canine basilar artery in a dose-dependent fashion.

  Structure-activity relationships (SAR) suggest that the 5-alkoxy group is an important pharmacophore in the production of the antihypertensive effect and that the introduction of a hydroxymethylene group on the side-chain, instead of the carbomethoxy group, changed the receptor affinity profile.

  一系列色胺类似物已被制备并测试其对5-HT1受体激动剂性质的影响。在吲哚核的C-5位置引入烷氧基导致在麻醉的自发性高血压大鼠（SHR）中产生短暂且剂量依赖的即刻降压和心率减慢反应。此外，在色胺的侧链的β-位置引入羰甲氧基功能显著增加了剖蛙大鼠的平均静息动脉血压（MAP），同时也以剂量依赖的方式导致犬基底动脉收缩。结构活性关系（SAR）表明，5-烷氧基团在产生降压效应中是一个重要的药效团，并且在侧链上引入羟甲基烷基，而不是羰甲氧基团，改变了受体亲和力谱。
• 3-Amino or amido-2-(1H-indol-3-yl) propanoic acid derivatives
  申请人：Miles Laboratories, Inc.

  公开号：US04283410A1

  公开（公告）日：1981-08-11

  Disclosed are compounds characterized by the structural formula: ##STR1## Various compounds circumscribed by the foregoing formula in which: R is H, CH.sub.3 or CH.sub.2 CH.sub.3, R' is H, or ##STR2## X is H, F or OCH.sub.3, Y is H or Cl, and Z is H or ##STR3## are therapeutically useful as anti-hypertensive agents.

  本发明涉及一种以结构式表示的化合物：##STR1## 其中，上述式中限定的各种化合物中：R为H，CH.sub.3或CH.sub.2 CH.sub.3，R'为H或##STR2## X为H，F或OCH.sub.3，Y为H或Cl，Z为H或##STR3## 作为抗高血压药物，这些化合物具有治疗作用。
• US4283336A
  申请人：——

  公开号：US4283336A

  公开（公告）日：1981-08-11
• US4283410A
  申请人：——

  公开号：US4283410A

  公开（公告）日：1981-08-11
• Tryptophan analogs. 1. Synthesis and antihypertensive activity of positional isomers
  作者：Max E. Safdy、Elva Kurchacova、Robert N. Schut、Horacio Vidrio、Enrique Hong

  DOI：10.1021/jm00348a022

  日期：1982.6

  A series of tryptophan analogues having the carboxyl function at the beta-position was synthesized and tested for antihypertensive activity. The 5-methoxy analogue 46 exhibited antihypertensive activity in the rat via the oral route and was much more potent than the normal tryptophan analogue. The methyl ester was found to be a critical structural feature for activity.