5-Chloro-2-(1H-indol-2-yl)-phenylamine | 174785-05-8

• 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-Chloro-2-(1H-indol-2-yl)-phenylamine
• 英文别名: 5-chloro-2-(1H-indol-2-yl)aniline
• CAS: 174785-05-8
• 化学式: C₁₄H₁₁ClN₂
• 分子量: 242.708
• InChiKey: OOTXVOYFJNCKFK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.8
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-Chloro-2-(1H-indol-2-yl)-phenylamine 在 溶剂黄146 、 sodium nitrite 作用下， 以 水 为溶剂， 反应 4.0h， 生成 3-Chloro-11H-indolo[3,2-c]cinnoline
  参考文献：
  名称：

  Indolo[3,2- c ]cinnolines with antiproliferative, antifungal, and antibacterial activity

  摘要：

  A series of indolo[3,2-c]cinnoline derivatives was prepared and tested to evaluate their biological activity. Most of them inhibited the proliferation of leukemia, lymphoma and solid tumor-derived cell lines at micromolar concentrations, whereas none of the compounds were active against HIV-1. With the exception of 7g, all title compounds showed antibacterial activity against grampositive bacteria, being up to 200 times more potent than the reference drug streptomycin. Some of the indolo[3,2-c]cinnolines were also endowed with good antifungal activity, particularly against Cryptococcus neoformans. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(99)00096-6
• 作为产物：
  描述：

  4-氯-2-硝基苯甲酰氯 在 吡啶 、 potassium tert-butylate 、 铁粉 、 溶剂黄146 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 13.5h， 生成 5-Chloro-2-(1H-indol-2-yl)-phenylamine
  参考文献：
  名称：

  Cirrincione; Almerico; Diana, Il Farmaco, 1995, vol. 50, # 12, p. 849 - 852

  摘要：

  DOI：

文献信息

• Derivatives of the New Ring System Indolo[1,2-<i>c</i>]benzo[1,2,3]triazine with Potent Antitumor and Antimicrobial Activity
  作者：Girolamo Cirrincione、Anna Maria Almerico、Paola Barraja、Patrizia Diana、Antonino Lauria、Alessandra Passannanti、Chiara Musiu、Alessandra Pani、Paola Murtas、Carla Minnei、M. Elena Marongiu、Paolo La Colla

  DOI：10.1021/jm9806087

  日期：1999.7.1

  Derivatives of the new ring system indolo[1,2-c]benzo[1,2,3]triazine 5 were synthesized by diazotization of substituted 2-(2-aminophenyl)indoles followed by an intramolecular coupling reaction of the diazonium group with the indole nitrogen. To obtain the indolobenzotriazine system it was necessary to protect the 3 position of the indole nucleus to avoid cyclization into the indolo[3,2-c]cinnoline

  新的环系统吲哚[1,2-c]苯并[1,2,3]三嗪5的衍生物是通过将取代的2-（2-氨基苯基）吲哚重氮化，然后将重氮基团与环己基进行分子内偶联反应而合成的。吲哚氮。为了获得吲哚并苯并三嗪系统，必须保护吲哚核的3位以避免环化成吲哚并[3,2-c] cinnoline系统4。在体外评估了吲哚并三嗪5a-g对一组白血病的抗肿瘤活性。 -，淋巴瘤，癌和神经母细胞瘤衍生的细胞系。一些化合物在亚微摩尔浓度下抑制T和B细胞系的增殖，而它们对实体肿瘤细胞系的活性则在微摩尔范围内。当评估其5a，d的抗真菌潜力可抑制某些测试的真菌，尽管浓度非常接近抑制人细胞增殖的浓度。相反，所有吲哚苯并三嗪被证明是相当有效和选择性的链球菌和葡萄球菌抑制剂。特别地，5b，c，g的效力比参考药物链霉素高80倍，并且以远低于对动物细胞的细胞毒性的浓度抑制上述革兰氏阳性细菌的生长。
• 2-(Aminoaryl)indoles and indolines, a process for their preparation and their use as medicaments
  申请人：HOECHST-ROUSSEL PHARMACEUTICALS INCORPORATED

  公开号：EP0406734A2

  公开（公告）日：1991-01-09

  There are described compounds of the formula where A is CH or N; X is hydrogen, loweralkyl, halogen, trifluromethyl, loweralkoxy, arylloweralkoxy, hydroxy or phenylamino; Y is hydrogen, loweralkyl, halogen, loweralkoxy, arylloweralkoxy or hydroxy; R1 is hydrogen or loweralkyl; R2 is hydrogen, loweralkyl, formyl, alkylcarbonyl, arylloweralkylcarbonyl, arylcarbonyl, alkoxycarbonyl, arylloweralkoxycarbonyl or aryloxycarbonyl; R3 is hydrogen, alkyl, alkylcarbonyl, arylloweralkylcarbonyl, arylcarbonyl, alkoxycarbonyl, arylloweralkoxycarbonyl, aryloxycarbonyl or -CH2CO2C2H5; which compounds are useful as topical antiinflammatory agents for the treatment of skin disorders, and a process for their preparation.

  所述化合物的化学式为 式中 A 是 CH 或 N X 是氢、低级烷基、卤素、三氟甲基、低级烷氧基、芳基低级烷氧基、羟基或苯基氨基； Y 是氢、低级烷基、卤素、低级烷氧基、芳基低级烷氧基或羟基； R1 是氢或低级烷基 R2 是氢、低级烷基、甲酰基、烷基羰基、芳基低级烷基羰基、芳基羰基、烷氧基羰基、芳基低级烷氧基羰基或芳基氧基羰基； R3 是氢、烷基、烷基羰基、芳低级烷基羰基、芳基羰基、烷氧基羰基、芳低级烷氧基羰基、芳氧基羰基或 -CH2CO2C2H5； 这些化合物可用作治疗皮肤病的局部消炎剂，以及制备这些化合物的工艺。
• US5166170A
  申请人：——

  公开号：US5166170A

  公开（公告）日：1992-11-24
• US5214059A
  申请人：——

  公开号：US5214059A

  公开（公告）日：1993-05-25
• Indolo[3,2- c ]cinnolines with antiproliferative, antifungal, and antibacterial activity
  作者：Paola Barraja、Patrizia Diana、Antonino Lauria、Alessandra Passannanti、Anna Maria Almerico、Carla Minnei、Silvia Longu、Donatella Congiu、Chiara Musiu、Paolo La Colla

  DOI：10.1016/s0968-0896(99)00096-6

  日期：1999.8

  A series of indolo[3,2-c]cinnoline derivatives was prepared and tested to evaluate their biological activity. Most of them inhibited the proliferation of leukemia, lymphoma and solid tumor-derived cell lines at micromolar concentrations, whereas none of the compounds were active against HIV-1. With the exception of 7g, all title compounds showed antibacterial activity against grampositive bacteria, being up to 200 times more potent than the reference drug streptomycin. Some of the indolo[3,2-c]cinnolines were also endowed with good antifungal activity, particularly against Cryptococcus neoformans. (C) 1999 Elsevier Science Ltd. All rights reserved.