3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxamide | 473257-94-2

• 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: 3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxamide
• 英文别名: 5-nitro-3-(3,5-dimethylphenylsulfonyl)-indole-2-carboxyamide；3-(3,5-dimethylphenyl)sulfonyl-5-nitro-1H-indole-2-carboxamide
• CAS: 473257-94-2
• 化学式: C₁₇H₁₅N₃O₅S
• 分子量: 373.389
• InChiKey: QERPCLSNHCDPDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  147
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxamide 在 platinum(IV) oxide 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 5-amino-3-(3,5-dimethylphenylsulfonyl)-indole-2-carboxyamide
  参考文献：
  名称：

  [EN] SUBSTITUTED PHENYLINDOLES FOR THE TREATMENT OF HIV
  [FR] PHENYLINDOLES SUBSTITUES DE TRAITEMENT DU VIH

  摘要：

  这项发明涉及苯基吲哚领域，用于治疗HIV感染，特别是对抗HIV耐药菌株具有显著活性的苯基吲哚。这些苯基吲哚在吲哚功能的苯环上至少有两个取代基，除了氢，最好在4'和5'、5'和6'或5'和7'位置，可选地与化合物的苯环上的3'和5'位置二取代结合，并且在化合物的吲哚基团的2号位置含有羧酰胺基团。甲基是苯环上取代的首选基团。吲哚功能的苯环的首选取代基包括但不限于氯、氟、溴、碘、CF3、甲氧基、CN和NO2。

  公开号：

  WO2004014364A1
• 作为产物：
  描述：

  ethyl 3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxylate 在 ammonium hydroxide 、 氯化铵 、 水 作用下， 反应 0.25h， 以60%的产率得到3-[(3,5-dimethylphenyl)sulfonyl]-5-nitro-1H-indole-2-carboxamide
  参考文献：
  名称：

  Indolylarylsulfones as HIV-1 Non-Nucleoside Reverse Transcriptase Inhibitors: New Cyclic Substituents at Indole-2-carboxamide

  摘要：

  New indolylarylsulfone derivatives bearing cyclic substituents at indole-2-carboxamide linked through a methylene/ethylene spacer were potent inhibitors of the WT HIV-1 replication in CEM and PBMC cells with inhibitory concentrations in the low nanomolar range. Against the mutant L100I and K103N RT HIV-1 strains in MT-4 cells, compounds 20, 24-26, 36, and 40 showed antiviral potency superior to that of NVP and EFV. Against these mutant strains, derivatives 20, 24-26, and 40 were equipotent to ETV. Molecular docking experiments on this novel series of IAS analogues have also suggested that the H-bond interaction between the nitrogen atom in the carboxamide chain of IAS and Glu138:B is important in the binding of these compounds. These results are in accordance with the experimental data obtained on the WT and on the mutant HIV-1 strains tested.

  DOI：

  10.1021/jm101614j

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。
• Substituted phenylindoles for the treatment of HIV
  申请人：——

  公开号：US20040180945A1

  公开（公告）日：2004-09-16

  This invention is in the area of phenylindoles that are useful for the treatment of HIV infection, and, in particular, phenylindoles that exhibit significant activity against resistant strains of HIV. The phenylindoles have at least two substituents other than hydrogen on the benzo ring of the indole function, preferably at the 4′ and 5′, 5′ and 6′ or the 5′ and 7′ positions, optionally in combination with disubstitution at positions 3″ and 5″ on the phenyl ring of the compound, and carboxamide containing moieties at position-2 on the indole group of the compound. Methyl is a preferred group for substitution on the phenyl ring. Preferred substituents for the benzo ring of the indole function include but are not limited to chlorine, fluorine, bromine, iodine, CF 3 , methoxy, CN, and NO 2 .

  本发明涉及苯基吲哚领域，其可用于治疗HIV感染，特别是对抗耐药性HIV的苯基吲哚。苯基吲哚在吲哚功能的苯环上至少有两个取代基，优选在4'和5'、5'和6'或5'和7'位置，可选地与化合物的苯环上的3''和5''位置的二取代结合，以及在化合物的吲哚基团的位置-2上含有羧酰胺基团。甲基是苯环取代的首选基团。吲哚功能的苯环的优选取代基包括但不限于氯、氟、溴、碘、CF3、甲氧基、CN和NO2。
• 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
• SUBSTITUTED PHENYLINDOLES FOR THE TREATMENT OF HIV
  申请人：Idenix (Cayman) Limited

  公开号：EP1545510A1

  公开（公告）日：2005-06-29