5-acetyl-3-(3,5-dimethylphenylsulfonyl)-indole-2-carboxyamide | 473257-95-3

• 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-acetyl-3-(3,5-dimethylphenylsulfonyl)-indole-2-carboxyamide
• 英文别名: 5-acetyl-3-(3,5-dimethylphenyl)sulfonyl-1H-indole-2-carboxamide
• CAS: 473257-95-3
• 化学式: C₁₉H₁₈N₂O₄S
• 分子量: 370.429
• InChiKey: CUCYAKKIDPRJAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-acetyl-3-(3,5-dimethylphenylsulfonyl)-indole-2-carboxyamide 在 sodium tetrahydroborate 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以83%的产率得到5-(1-hydroxyethyl)-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：

  3,5-二甲基苯硫酚 在 ammonium hydroxide 、 三氟化硼乙醚 、 氯化铵 、 间氯过氧苯甲酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 9.0h， 生成 5-acetyl-3-(3,5-dimethylphenylsulfonyl)-indole-2-carboxyamide
  参考文献：
  名称：

  Novel Indolyl Aryl Sulfones Active against HIV-1 Carrying NNRTI Resistance Mutations:  Synthesis and SAR Studies

  摘要：

  The potent anti-HIV-1 activities of L-737,126 (2) and PAS sulfones prompted us to design and test against HIV-1 in acutely infected MT-4 cells a number of novel 1- and 3-benzenesulfonylindoles. Indoles belonging to the 1-benzenesulfonyl series were found poorly or totally inactive. On the contrary, some of the 3-benzenesulfonyl derivatives turned out to be as potent as 2, being endowed with potencies in the low nanomolar concentration range. In particular, (2-methylphenyl)sulfonyl (72) and (3-methylphenyl)sulfonyl (73) derivatives showed EC50 values of 1 nM. Introduction of two methyl groups at positions 3 and 5 of the phenyl ring of 2 furnished derivatives (80 and 83) which showed very potent and selective anti-HIV-1 activity not only against the wt strain, but also against mutants carrying NNRTI-resistant mutations at positions 103 and 181 of the reverse transcriptase gene.

  DOI：

  10.1021/jm0211063

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。
• [EN] SUBSTITUTED PHENYLINDOLES FOR THE TREATMENT OF HIV<br/>[FR] PHENYLINDOLES SUBSTITUES DE TRAITEMENT DU VIH
  申请人：IDENIX CAYMAN LTD

  公开号：WO2004014364A1

  公开（公告）日：2004-02-19

  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, CF3, methoxy, CN, and NO2­.

  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。
• 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