2-[4-(methylsulfonyl)phenyl]-1H-indole | 203198-46-3

• 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: 2-[4-(methylsulfonyl)phenyl]-1H-indole
• 英文别名: 2-[4-(methylsulfonyl)phenyl]indole；2-(4-methylsulfonylphenyl)-1H-indole
• CAS: 203198-46-3
• 化学式: C₁₅H₁₃NO₂S
• 分子量: 271.34
• InChiKey: ABMIPIMSKSYQKK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  58.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-[4-(methylsulfonyl)phenyl]-1H-indole 在 4-二甲氨基吡啶 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 生成 2-amino-4-(2-(4-(methylsulfonyl)phenyl)-1H-indol-3-yl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile
  参考文献：
  名称：

  Microwave-assisted synthesis of 3′-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity

  摘要：

  A new series of indole-based chromene derivatives 4a-4p has been synthesized by one pot cyclocondensation reaction of 2-phenyl-1H-indole-3-carbaldehyde 1a-1h; malononitrile 2; and 1,3-cyclohexanedione/dimedone 3a/b under microwave irradiation catalyzed by an organocatalyst 4-(N,N-dimethylamino) pyridine. Easy experimental procedure, high yield, selectivity, and shorter reaction time are the imperative features of this method. All the compounds were screened against a representative panel of bacteria and fungi. Some of the compounds are found to be equipotent or more potent than that of standard drugs as evident from SAR study.

  DOI：

  10.1007/s00044-011-9861-4
• 作为产物：
  描述：

  4-甲砜基苯乙酮 在 polyphosphoric acid 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 生成 2-[4-(methylsulfonyl)phenyl]-1H-indole
  参考文献：
  名称：

  Microwave-assisted synthesis of 3′-indolyl substituted 4H-chromenes catalyzed by DMAP and their antimicrobial activity

  摘要：

  A new series of indole-based chromene derivatives 4a-4p has been synthesized by one pot cyclocondensation reaction of 2-phenyl-1H-indole-3-carbaldehyde 1a-1h; malononitrile 2; and 1,3-cyclohexanedione/dimedone 3a/b under microwave irradiation catalyzed by an organocatalyst 4-(N,N-dimethylamino) pyridine. Easy experimental procedure, high yield, selectivity, and shorter reaction time are the imperative features of this method. All the compounds were screened against a representative panel of bacteria and fungi. Some of the compounds are found to be equipotent or more potent than that of standard drugs as evident from SAR study.

  DOI：

  10.1007/s00044-011-9861-4

文献信息

• Rh-catalyzed intramolecular sp2 C–H bond difluoromethylenation
  作者：Yajun Li、Jiangtao Zhu、Haibo Xie、Shan Li、Dongjie Peng、Zhengke Li、Yongming Wu、Yuefa Gong

  DOI：10.1039/c2cc30207a

  日期：——

  A new Rh-catalyzed intramolecular coupling reaction of a CF2Br group with a 2-aryl of indole or pyrrolevia C–H bond activation is presented. This reaction represents a new way of incorporating difluoromethylene groups into organic compounds. Preliminary mechanistic studies suggest that this reaction might not occur via a conventional free radical pathway.

  一种新的Rh催化的CF2Br基团与吲哚或吡咯的2-芳基间的分子内偶联反应被提出，经过C–H键活化。该反应代表了将二氟亚甲基团引入有机化合物的新方式。初步的机理研究表明，该反应可能不是通过传统的自由基途径进行的。
• Design and Synthesis of Some 5-Substituted-2-(4-(azido or methylsulfonyl) phenyl)-1H-indole Derivatives as Selective Cyclooxygenase (COX-2) Inhibitors
  作者：Afshin Zarghi

  DOI：10.3797/scipharm.0805-20

  日期：——

  A group of 5-substituted-2-(4-azido or (methylsulfonyl)phenyl)-1H-indoles were designed and synthesized as selective cyclooxygenase (COX-2) inhibitors. In vitro COX-1 and COX-2 isozyme inhibition studies were carried out to investigate the effect of different substituents (H, F, Cl, Me, OMe) at C-5 position and different pharmacophore groups (azido or methylsulfonyl) at para position of phenyl ring at C-2 position of the 1H-indole ring on COX-2 selectivity and potency. The structure-activity relationship study of these compounds indicated that the introduction of a methoxy substituent at C-5 position and 4-(methylsulfonyl) phenyl group at C-2 position of the 1H-indole ring (compound 4e) had the best COX-2 selectivity (S.I= 291.2). A molecular modeling study where 4e was docked in the binding site of COX-2 showed that the methylsulfonyl group at para position of phenyl ring is oriented in the vicinity of the COX-2 secondary pocket.

  设计并合成了一组 5-取代-2-(4-叠氮基或(甲基磺酰基)苯基)-1H-吲哚作为选择性环氧合酶 (COX-2) 抑制剂。进行体外COX-1和COX-2同工酶抑制研究，以研究C-5位不同取代基（H、F、Cl、Me、OMe）和对位不同药效基团（叠氮基或甲磺酰基）的影响1H-吲哚环 C-2 位上的苯环对 COX-2 选择性和效力的影响。这些化合物的构效关系研究表明，在1H-吲哚环的C-5位引入甲氧基取代基和在1H-吲哚环的C-2位引入4-(甲基磺酰基)苯基(化合物4e)具有最佳的COX- 2 选择性（S.I=291.2）。 4e 对接在 COX-2 结合位点的分子模型研究表明，苯环对位的甲基磺酰基定向在 COX-2 二级口袋附近。
• Bimetallic Catalyzed Synthesis of 2-Arylindoles
  作者：M. Manuel B. Marques、Rita Ferro、Nuno Viduedo、A. Sofia Santos、Artur M. S. Silva、Beatriz Royo

  DOI：10.1055/a-2035-6420

  日期：——

  A bimetallic synthesis of 2-arylindoles from alcohols and anilines is described. The dehydrogenation or oxidation of a secondary alcohol was performed by Ni- or Mn-catalyzed reactions, respectively. The formed ketone was converted into an imine intermediate that was later cyclized to the corresponding 2-arylindole by a Pd-catalyzed oxidative cyclization. A series of 2-arylindoles were prepared without

  描述了从醇和苯胺双金属合成 2-芳基吲哚。仲醇的脱氢或氧化分别通过 Ni 或 Mn 催化的反应进行。形成的酮转化为亚胺中间体，随后通过 Pd 催化的氧化环化反应生成相应的 2-芳基吲哚。在不分离产生的中间体的情况下制备了一系列 2-芳基吲哚。研究了催化剂的相容性，优化后的方案为整合地球上丰富的金属和钯配合物开辟了空间，以提高 N-杂环合成的可持续性。
• 1,2-DIARYLINDOLES EN TANT QU'INHIBITEURS DE COX-2
  申请人：LABORATOIRES UPSA

  公开号：EP0915848A1

  公开（公告）日：1999-05-19
• US5723485A
  申请人：——

  公开号：US5723485A

  公开（公告）日：1998-03-03