5-苯基-1H-吲哚-7-羧酰胺 | 860625-06-5

• 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
• 中文名称: 5-苯基-1H-吲哚-7-羧酰胺
• 英文名称: 5-phenyl-1H-indole-7-carboxamide
• CAS: 860625-06-5
• 化学式: C₁₅H₁₂N₂O
• 分子量: 236.273
• InChiKey: IOAHDHUZGJTQFJ-UHFFFAOYSA-N

物化性质

• 沸点：
  505.3±38.0 °C(Predicted)
• 密度：
  1.271±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  5-苯基-1H-吲哚-7-羧酰胺 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 3-iodo-5-phenyl-1H-indole-7-carboxamide
  参考文献：
  名称：

  [EN] INDOLE DERIVATIVES AND USE THEREOF AS KINASE INHIBITORS IN PARTICULAR IKK2 INHIBITORS
  [FR] DERIVES D'INDOLE ET UTILISATION DE CEUX-CI COMME INHIBITEURS DE KINASE, NOTAMMENT DES INHIBITEURS DE IKK2

  摘要：

  提供式(I)的吲哚羧酰胺化合物作为激酶活性的抑制剂，特别是IKK2活性的抑制剂，以及含有它们的组合物和药物，用于炎症和组织修复障碍的治疗。

  公开号：

  WO2005067923A1
• 作为产物：
  描述：

  1-(1,1-dimethylethyl) 7-ethyl 2,3-dihydro-1H-indole-1,7-dicarboxylate 在 potassium phosphate 、 N-溴代丁二酰亚胺(NBS) 、 2'-(dimethylamino)-2-biphenylyl-palladium(II) chloride dinorbornylphosphine complex 、 氨 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium hydroxide 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 71.0h， 生成 5-苯基-1H-吲哚-7-羧酰胺
  参考文献：
  名称：

  3,5-Disubstituted-indole-7-carboxamides as IKKβ Inhibitors: Optimization of Oral Activity via the C3 Substituent

  摘要：

  I kappa B kinase beta (IKK beta or IKK2) is a key regulator of nuclear factor kappa B (NF-kappa B) and has received attention as a therapeutic target. Herein we report on the optimization of a series of 3,5-disubstituted-indole-7-carboxamides for oral activity. In doing so, we focused attention on potency, ligand efficiency (LE), and physicochemical properties and have identified compounds 24 and (R)-28 as having robust in vivo activity.

  DOI：

  10.1021/acsmedchemlett.8b00291

文献信息

• Chemical Compounds
  申请人：Kerns K. Jeffrey

  公开号：US20070254873A1

  公开（公告）日：2007-11-01

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及新型吲哚羧酰胺衍生物。具体而言，本发明涉及公式I所示的化合物：其中R1，R2，R3，U和V如下所定义，及其药学上可接受的盐。本发明的化合物是IKK2的抑制剂，可用于治疗与不适当的IKK2（也称为IKKβ）活性有关的疾病，如类风湿性关节炎、哮喘和COPD（慢性阻塞性肺疾病）。因此，本发明还涉及包含本发明化合物的药物组合物。本发明还进一步涉及使用本发明化合物或包含本发明化合物的药物组合物来抑制IKK2活性和治疗与此相关的疾病的方法。
• Indole Derivatives and Use Thereof as Kinase Inhibitors in Particular Ikk2 Inhibitors
  申请人：Baldwin Ian Robert

  公开号：US20080269200A1

  公开（公告）日：2008-10-30

  Indole carboxamide compounds of Formula (I): are provided as inhibitors of kinase activity, in particular IKK2 activity as well as compositions and medicaments containing them, for use in inflammatory and tissue repair disorders.

  提供一种式子为(I)的吲哚羧酰胺化合物，作为激酶活性的抑制剂，特别是IKK2活性的抑制剂，并提供包含它们的组合物和药物，用于治疗炎症和组织修复性疾病。
• Chemical compounds
  申请人：Glaxo Group Limited

  公开号：US07858796B2

  公开（公告）日：2010-12-28

  The invention is directed to novel indole carboxamide derivatives. Specifically, the invention is directed to compounds according to formula I: where R1, R2, R3, U and V are defined below and to pharmaceutically acceptable salts thereof. The compounds of the invention are inhibitors of IKK2 and can be useful in the treatment of disorders associated with inappropriate IKK2 (also known as IKKβ) activity, such as rheumatoid arthritis, asthma, and COPD (chronic obstructive pulmonary disease). Accordingly, the invention is further directed to pharmaceutical compositions comprising a compound of the invention. The invention is still further directed to methods of inhibiting IKK2 activity and treatment of disorders associated therewith using a compound of the invention or a pharmaceutical composition comprising a compound of the invention.

  本发明涉及新型吲哚羧酰胺衍生物。具体而言，本发明涉及公式I所示的化合物，其中R1、R2、R3、U和V的定义如下，以及其药学上可接受的盐。本发明的化合物是IKK2的抑制剂，可用于治疗与不适当IKK2（也称为IKKβ）活性相关的疾病，如类风湿性关节炎、哮喘和COPD（慢性阻塞性肺疾病）。因此，本发明还涉及包含该化合物的制药组合物。本发明还进一步涉及使用该化合物或包含该化合物的制药组合物来抑制IKK2活性和治疗与之相关的疾病的方法。
• [EN] CHEMICAL COMPOUNDS<br/>[FR] COMPOSES CHIMIQUES
  申请人：GLAXO GROUP LTD

  公开号：WO2006034317A3

  公开（公告）日：2007-04-19
• 3,5-Disubstituted-indole-7-carboxamides: The discovery of a novel series of potent, selective inhibitors of IKK-β
  作者：David D. Miller、Paul Bamborough、John A. Christopher、Ian R. Baldwin、Aurelie C. Champigny、Geoffrey J. Cutler、Jeffrey K. Kerns、Timothy Longstaff、Geoffrey W. Mellor、James V. Morey、Mary A. Morse、Hong Nie、William L. Rumsey、John J. Taggart

  DOI：10.1016/j.bmcl.2011.02.107

  日期：2011.4

  The discovery and hit-to-lead exploration of a novel series of selective IKK-beta kinase inhibitors is described. The initial lead fragment 3 was identified by pharmacophore-directed virtual screening. Homology model-driven SAR exploration of the template led to potent inhibitors, such as 12, which demonstrate efficacy in cellular assays and possess encouraging developability profiles. (C) 2011 Elsevier Ltd. All rights reserved.