(5-chloro-3-(1-phenylcyclopropyl)-1H-indol-2-yl)methanol | 1374964-87-0

• 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-3-(1-phenylcyclopropyl)-1H-indol-2-yl)methanol
• 英文别名: [5-chloro-3-(1-phenylcyclopropyl)-1H-indol-2-yl]methanol
• CAS: 1374964-87-0
• 化学式: C₁₈H₁₆ClNO
• 分子量: 297.784
• InChiKey: NDXYHPYTJQLBDW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  36
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  1-tert-butyl 2-ethyl 5-chloro-3-(1-phenylvinyl)-1H-indole-1,2-dicarboxylate 在 lithium aluminium tetrahydride 、 diethylzinc 、 三氟乙酸 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 3.33h， 生成 (5-chloro-3-(1-phenylcyclopropyl)-1H-indol-2-yl)methanol
  参考文献：
  名称：

  Novel Cyclopropyl-Indole Derivatives as HIV Non-Nucleoside Reverse Transcriptase Inhibitors

  摘要：

  The HIV pandemic represents one of the most serious diseases to face mankind in both a social and economic context, with many developing nations being the worst afflicted. Due to ongoing resistance issues associated with the disease, the design and synthesis of anti-HIV agents presents a constant challenge for medicinal chemists. Utilizing molecular modeling, we have designed a series of novel cyclopropyl indole derivatives as HIV non-nucleoside reverse transcriptase inhibitors and carried out their preparation. These compounds facilitate a double hydrogen bonding interaction to Lys101 and efficiently occupy the hydrophobic pockets in the regions of Tyr181/188 and Val179. Several of these compounds inhibited HIV replication as effectively as nevirapine when tested in a phenotypic assay.

  DOI：

  10.1021/ml3000462

文献信息

• Novel Cyclopropyl-Indole Derivatives as HIV Non-Nucleoside Reverse Transcriptase Inhibitors
  作者：Mohammad Hassam、Adriaan E. Basson、Dennis C. Liotta、Lynn Morris、Willem A. L. van Otterlo、Stephen C. Pelly

  DOI：10.1021/ml3000462

  日期：2012.6.14

  The HIV pandemic represents one of the most serious diseases to face mankind in both a social and economic context, with many developing nations being the worst afflicted. Due to ongoing resistance issues associated with the disease, the design and synthesis of anti-HIV agents presents a constant challenge for medicinal chemists. Utilizing molecular modeling, we have designed a series of novel cyclopropyl indole derivatives as HIV non-nucleoside reverse transcriptase inhibitors and carried out their preparation. These compounds facilitate a double hydrogen bonding interaction to Lys101 and efficiently occupy the hydrophobic pockets in the regions of Tyr181/188 and Val179. Several of these compounds inhibited HIV replication as effectively as nevirapine when tested in a phenotypic assay.