ethyl 3-[(3,5-dimethylphenyl)thio]-5-nitro-1H-indole-2-carboxylate | 473257-72-6

• 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 3-[(3,5-dimethylphenyl)thio]-5-nitro-1H-indole-2-carboxylate
• 英文别名: ethyl 3-(3,5-dimethylphenyl)sulfanyl-5-nitro-1H-indole-2-carboxylate
• CAS: 473257-72-6
• 化学式: C₁₉H₁₈N₂O₄S
• 分子量: 370.429
• InChiKey: CTUQETMXOHPVQI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  113
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ethyl 3-[(3,5-dimethylphenyl)thio]-5-nitro-1H-indole-2-carboxylate 在 间氯过氧苯甲酸 作用下， 以 氯仿 为溶剂， 以53%的产率得到ethyl 3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxylate
  参考文献：
  名称：

  Indolylarylsulfones Bearing Natural and Unnatural Amino Acids. Discovery of Potent Inhibitors of HIV-1 Non-Nucleoside Wild Type and Resistant Mutant Strains Reverse Transcriptase and Coxsackie B4 Virus

  摘要：

  New potent indolylarylsulfone (IAS) HIV-I NNRTIs were obtained by coupling natural and unnatural amino acids to the 2-carboxamide and introducing different electron-withdrawing substituents at position 4 and 5 of the indole nucleus. The new IASs inhibited the HIV-1 replication in human T-lymphocyte (CEM) cells at low/subnanomolar concentration and were weakly cytostatic. Against the mutant L100I, K103N, and Y181C RT HIV-1 strains in CEM cells, sulfones 3, 4, 19, 27, and 31 were comparable to EFV. The new IASs were inhibitors to Coxsackie B4 virus at low micromolar (2-9 mu M) concentrations. Superimposition of PLANTS docked conformations of IASs 19 and 9 revealed different hydrophobic interactions of the 3,5-dimethylphenyl group, for which a staking interaction with Tyr181 aromatic side chain was observed. The binding mode of 19 was not affected by the L100I mutation and was consistent with the interactions reported for the WT strain.

  DOI：

  10.1021/jm801470b
• 作为产物：
  描述：

  5-硝基吲哚-2-羧酸乙酯 、 1-(3,5-dimethylphenylthio)pyrrolidine-2,5-dione 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以53%的产率得到ethyl 3-[(3,5-dimethylphenyl)thio]-5-nitro-1H-indole-2-carboxylate
  参考文献：
  名称：

  Indolylarylsulfones Bearing Natural and Unnatural Amino Acids. Discovery of Potent Inhibitors of HIV-1 Non-Nucleoside Wild Type and Resistant Mutant Strains Reverse Transcriptase and Coxsackie B4 Virus

  摘要：

  New potent indolylarylsulfone (IAS) HIV-I NNRTIs were obtained by coupling natural and unnatural amino acids to the 2-carboxamide and introducing different electron-withdrawing substituents at position 4 and 5 of the indole nucleus. The new IASs inhibited the HIV-1 replication in human T-lymphocyte (CEM) cells at low/subnanomolar concentration and were weakly cytostatic. Against the mutant L100I, K103N, and Y181C RT HIV-1 strains in CEM cells, sulfones 3, 4, 19, 27, and 31 were comparable to EFV. The new IASs were inhibitors to Coxsackie B4 virus at low micromolar (2-9 mu M) concentrations. Superimposition of PLANTS docked conformations of IASs 19 and 9 revealed different hydrophobic interactions of the 3,5-dimethylphenyl group, for which a staking interaction with Tyr181 aromatic side chain was observed. The binding mode of 19 was not affected by the L100I mutation and was consistent with the interactions reported for the WT strain.

  DOI：

  10.1021/jm801470b

文献信息

• Phenylindoles for the treatment of HIV
  申请人：——

  公开号：US20020193415A1

  公开（公告）日：2002-12-19

  The invention as disclosed herein is a method and composition for the treatment of HIV in humans and other host animals, that includes the administration of an effective HIV treatment amount of a phenylindole as described herein or a pharmaceutically acceptable salt or prodrug thereof, optionally in a pharmaceutically acceptable carrier. The compounds of this invention either possess antiviral (i.e., anti-HIV) activity, or are metabolized to a compound that exhibits such activity.

  本发明公开了一种用于治疗人类和其他宿主动物体内的HIV的方法和组合物，包括根据本文所述的给予有效的HIV治疗量的苯基吲哚或其药学上可接受的盐或前药，可选地在药学上可接受的载体中。本发明的化合物具有抗病毒（即抗HIV）活性，或者经代谢后形成具有该活性的化合物。
• PHENYLINDOLES FOR THE TREATMENT OF HIV
  申请人：Idenix (Cayman) Limited

  公开号：EP1390029A1

  公开（公告）日：2004-02-25
• EP1390029A4
  申请人：——

  公开号：EP1390029A4

  公开（公告）日：2005-11-30
• US6710068B2
  申请人：——

  公开号：US6710068B2

  公开（公告）日：2004-03-23
• [EN] PHENYLINDOLES FOR THE TREATMENT OF HIV<br/>[FR] PHENYLINDOLES POUR LE TRAITEMENT DE L'INFECTION PAR LE VIH
  申请人：IDENIX CAYMAN LTD

  公开号：WO2002083126A1

  公开（公告）日：2002-10-24

  The invention as disclosed herein is a method and composition for the treatment of HIV in humans and other host animals, that includes the administration of an effective HIV treatment amount of a phenylindole as described herein or a pharmaceutically acceptable salt or prodrug thereof, optionally in a pharmaceutically acceptable carrier. The compounds of this invention either possess antiviral (i.e., anti-HIV) activity, or are metabolized to a compound that exhibits such activity.