ethyl 1-oxiranylmethyl-4-phenyl-1H-pyrrole-3-carboxylate | 483341-10-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: ethyl 1-oxiranylmethyl-4-phenyl-1H-pyrrole-3-carboxylate
• CAS: 483341-10-2
• 化学式: C₁₆H₁₇NO₃
• 分子量: 271.316
• InChiKey: ZPBIDESYUZBGBI-UHFFFAOYSA-N

物化性质

• 沸点：
  442.6±35.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.73
• 重原子数：
  20.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 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：

  ethyl 1-oxiranylmethyl-4-phenyl-1H-pyrrole-3-carboxylate 在 三甲基铝 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 18.0h， 生成 Ethyl 1-[3-[2-(tert-butylcarbamoyl)phenyl]sulfanyl-2-hydroxy-propyl]-4-phenyl-pyrrole-3-carboxylate
  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：

  4-苯基吡咯-3-甲酸乙酯 、 环氧氯丙烷 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以42%的产率得到ethyl 1-oxiranylmethyl-4-phenyl-1H-pyrrole-3-carboxylate
  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