5-Chloro-1-oxiranylmethyl-1H-indole-2-carboxylic acid ethyl ester | 483341-09-9

• 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: 5-Chloro-1-oxiranylmethyl-1H-indole-2-carboxylic acid ethyl ester
• CAS: 483341-09-9
• 化学式: C₁₄H₁₄ClNO₃
• 分子量: 279.723
• InChiKey: RXWORZSFNAFOBP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  43.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  5-Chloro-1-oxiranylmethyl-1H-indole-2-carboxylic acid ethyl ester 在 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 17.0h， 生成 1-[3-(2-tert-Butylcarbamoyl-phenylamino)-2-hydroxy-propyl]-5-chloro-1H-indole-2-carboxylic acid tert-butylamide
  参考文献：
  名称：

  Design, synthesis and QSAR studies on N-aryl heteroarylisopropanolamines, a new class of non-peptidic HIV-1 protease inhibitors

  摘要：

  A series of N-aryl heteroarylisopropanolamines in which an indole or a 3-arylpyrrole moiety was linked to an aryl group through an isopropanolamine linker, were designed and synthesized as potential anti-HIV-1-PR agents. Series was tested for their ability in blocking PR activity. As a rule, indole derivatives of class I exhibited more potency than pyrrole analogues of class 2 while tert-butylamide substituents increased anti-PR potency. In fact, bis tert-butylamide le showed the highest activity with IC50 = 25 muM. Even if not very potent, a simple class of anti-PR agents, with a facile synthetic pathway was discovered. QSAR Studies on isopropanolamines I and 2 were performed in comparison with diarylbutanols, a new class of non peptidic anti-PR agents, recently discovered by Agouron Pharmaceuticals. QSAR and CoMFA models based on 30 diarylbutanols used as a training set were developed. The obtained models were used to investigate the binding mode of the newly synthesized derivatives I and 2. The results of this study suggest that N-aryl heteroarylisopropanolamines bind to the PR active site similarly to the diarylbutanols of Agouron. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(02)00119-0
• 作为产物：
  描述：

  5-氯吲哚-2-羧酸乙酯 、 环氧氯丙烷 在 potassium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以69 %的产率得到5-Chloro-1-oxiranylmethyl-1H-indole-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Convenient Synthesis of N-Heterocycle-Fused Tetrahydro-1,4-Diazepinones

  摘要：

  介绍了合成四氢-4H-吡唑并[1,5-a][1,4]二氮杂卓-4-酮、四氢[1,4]二氮杂卓[1,2-a]吲哚-1-酮和四氢-1H-苯并[4,5]咪唑并[1,2-a][1,4]二氮杂卓-1-酮衍生物的一般方法。研究人员开发了一种区域选择性策略，从易于获得的 3(5)-芳基-或甲基-1H-吡唑-5(3)-羧酸乙酯合成 1-(环氧乙烷-2-基甲基)-1H-吡唑-5-羧酸乙酯。得到的中间体进一步用胺处理，导致环氧乙烷开环和直接环化，产生目标吡唑并[1,5-a][1,4]二氮杂卓-4-酮。目前的研究采用了简单的两步合成法，并成功地将 1H-indole- 乙酯和 1H-苯并[d]咪唑-2-甲酸乙酯功能化。融合杂环化合物的结构通过 1H、13C 和 15N-NMR 光谱以及 HRMS 调查得到了证实。

  DOI：

  10.3390/molecules27248666