Ethyl 1-[3-(2-ethoxycarbonylphenyl)sulfanyl-2-hydroxy-propyl]-4-phenyl-pyrrole-3-carboxylate | 483341-34-0

• 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-[3-(2-ethoxycarbonylphenyl)sulfanyl-2-hydroxy-propyl]-4-phenyl-pyrrole-3-carboxylate
• 英文别名: ethyl 1-[3-(2-ethoxycarbonylphenyl)sulfanyl-2-hydroxypropyl]-4-phenylpyrrole-3-carboxylate
• CAS: 483341-34-0
• 化学式: C₂₅H₂₇NO₅S
• 分子量: 453.559
• InChiKey: UWEWCIMKZWTZLL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  叔丁胺 、 Ethyl 1-[3-(2-ethoxycarbonylphenyl)sulfanyl-2-hydroxy-propyl]-4-phenyl-pyrrole-3-carboxylate 在 三甲基铝 作用下， 以 甲苯 为溶剂， 反应 12.0h， 以34%的产率得到N-tert-butyl-1-[3-[2-(tert-butylcarbamoyl)phenyl]sulfanyl-2-hydroxy-propyl]-4-phenyl-pyrrole-3-carboxamide
  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 在 potassium carbonate 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.0h， 生成 Ethyl 1-[3-(2-ethoxycarbonylphenyl)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