ethyl 5-chloro-3-(thiophene-2-carbonyl)-1H-indole-2-carboxylate | 1374964-60-9

• 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: ethyl 5-chloro-3-(thiophene-2-carbonyl)-1H-indole-2-carboxylate
• CAS: 1374964-60-9
• 化学式: C₁₆H₁₂ClNO₃S
• 分子量: 333.795
• InChiKey: JOBBITRPCYTBSG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.29
• 重原子数：
  22.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  59.16
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  ethyl 5-chloro-3-(thiophene-2-carbonyl)-1H-indole-2-carboxylate 在 4-二甲氨基吡啶 、 正丁基锂 、 diethylzinc 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.66h， 生成 ethyl 5-chloro-3-(1-(thiophen-2-yl)cyclopropyl)-1H-indole-2-carboxylate
  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
• 作为产物：
  描述：

  2-噻吩甲酰氯 、 5-氯吲哚-2-羧酸乙酯 在 aluminum (III) chloride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以83%的产率得到ethyl 5-chloro-3-(thiophene-2-carbonyl)-1H-indole-2-carboxylate
  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