ethyl 5-chloro-3-(1-(thiophen-2-yl)cyclopropyl)-1H-indole-2-carboxylate | 1374964-76-7

• 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-(1-(thiophen-2-yl)cyclopropyl)-1H-indole-2-carboxylate
• 英文别名: ethyl 5-chloro-3-[1-(2-thienyl)cyclopropyl]-1H-indole-2-carboxylate；ethyl 5-chloro-3-(1-thiophen-2-ylcyclopropyl)-1H-indole-2-carboxylate
• CAS: 1374964-76-7
• 化学式: C₁₈H₁₆ClNO₂S
• 分子量: 345.85
• InChiKey: NDOGHMBHZXTNIT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  70.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  ethyl 5-chloro-3-(1-(thiophen-2-yl)cyclopropyl)-1H-indole-2-carboxylate 在 potassium hydroxide 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 以92%的产率得到5-chloro-3-(1-(thiophen-2-yl)cyclopropyl)-1H-indole-2-carboxylic acid
  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：

  5-氯吲哚-2-羧酸乙酯 在 4-二甲氨基吡啶 、 aluminum (III) chloride 、 正丁基锂 、 diethylzinc 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 8.66h， 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

文献信息

• [EN] SUBSTITUTED INDOLES AND THEIR USE AS NON-NUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITORS<br/>[FR] INDOLES SUBSTITUÉS ET LEUR UTILISATION EN TANT QU'INHIBITEURS NON-NUCLÉOSIDIQUES DE LA TRANSCRIPTASE INVERSE
  申请人：UNIV STELLENBOSCH

  公开号：WO2015044928A1

  公开（公告）日：2015-04-02

  Compounds of Formula I or pharmaceutically acceptable salts thereof are claimed, wherein R1 is an ester, amide or a heterocycle; R2 is C or N; R3 is a methoxy or ethoxy group, an alkyl group or a heterocyclic group; R4 is a substituted or unsubstituted phenyl or heteroaromatic group; and R5 is a halide or a nitrile. The use of these compounds as non-nucleoside reverse transcriptase inhibitors (NNRTIs) for inhibiting or treating HIV infection or AIDS is also described.

  本发明涉及化合物I的配方或其药学上可接受的盐，其中R1是酯、酰胺或杂环；R2是C或N；R3是甲氧基或乙氧基基团、烷基或杂环基团；R4是取代或未取代的苯基或杂环芳基；R5是卤素或腈基。本发明还描述了这些化合物作为非核苷类逆转录酶抑制剂（NNRTIs）用于抑制或治疗HIV感染或艾滋病的用途。
• 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.