5-formyl-N,N-dimethyl-1H-indole-1-carboxamide | 1025763-25-0

• 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-formyl-N,N-dimethyl-1H-indole-1-carboxamide
• 英文别名: 5-formyl-N,N-dimethylindole-1-carboxamide
• CAS: 1025763-25-0
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: KNXPBUHPXWFIGJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  42.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-formyl-N,N-dimethyl-1H-indole-1-carboxamide 在 三氟化硼乙醚 、 sodium hydroxide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 二甲基亚砜 为溶剂， 生成 3-(1H-indol-5-yl)-2,2-dimethyl-3-phenylpropanoic acid
  参考文献：
  名称：

  Heterocyclic glucocorticoid receptor modulators with a 2,2-dimethyl-3-phenyl-N-(thiazol or thiadiazol-2-yl)propanamide core

  摘要：

  A series of heterocyclic glucocorticoid receptor (GR) modulators with 2,2-dimethyl-3-phenyl-N-(thiazol or thiadiazol-2-yl) propanamide core are described. Structure-activity relationships suggest a combination of H-bond acceptor and a 4-fluorophenyl moiety as being important structural components contributing to the glucocorticoid receptor binding and functional activity for this series of GR modulators. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.049
• 作为产物：
  描述：

  5-吲哚甲醛 、 二甲氨基甲酰氯 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以97%的产率得到5-formyl-N,N-dimethyl-1H-indole-1-carboxamide
  参考文献：
  名称：

  Heterocyclic glucocorticoid receptor modulators with a 2,2-dimethyl-3-phenyl-N-(thiazol or thiadiazol-2-yl)propanamide core

  摘要：

  A series of heterocyclic glucocorticoid receptor (GR) modulators with 2,2-dimethyl-3-phenyl-N-(thiazol or thiadiazol-2-yl) propanamide core are described. Structure-activity relationships suggest a combination of H-bond acceptor and a 4-fluorophenyl moiety as being important structural components contributing to the glucocorticoid receptor binding and functional activity for this series of GR modulators. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.08.049

文献信息

• Iron-Catalyzed Cross Dehydrogenative Coupling (CDC) of Indoles and Benzylic CH Bonds
  作者：Shuaibo Guo、Yaxuan Li、Yu Wang、Xin Guo、Xu Meng、Baohua Chen

  DOI：10.1002/adsc.201400938

  日期：2015.3.23

  An efficient method for the synthesis of 3‐alkylated indoles is described. The oxidative cross‐coupling reaction of diphenylmethane derivatives with indoles at the C‐3 position was achieved employing the N,N‐dimethylcarbamoyl moiety as an auxiliary group in the presence of iron(II) chloride (FeCl2) and 2,3‐dichloro‐5,6‐dicyanoquinone (DDQ).

  描述了一种合成3-烷基化吲哚的有效方法。在氯化铁（II）（FeCl 2）和2,3-二氯的存在下，使用N，N-二甲基氨基甲酰基部分作为辅助基团，实现了二苯基甲烷衍生物与吲哚在C-3位置的氧化交叉偶联反应。-5,6-二氰基醌（DDQ）。
• MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1, AND/OR NF-kB ACTIVITY AND USE THEREOF
  申请人：Sheppeck James E.

  公开号：US20100076014A1

  公开（公告）日：2010-03-25

  Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, and/or AP-1, and/or NF-κB activity including inflammatory and immune diseases, obesity and diabetes having the structure of formula (I), its enantiomers, diastereomers, or a pharmaceutically-acceptable salt, or hydrate, thereof, wherein (Ia) is heterocycle or heteroaryl; J, Ja, E, F, G, Ma, M, Q, Za and Z are as defined herein. Also provided are pharmaceutical compositions and methods of treating inflammatory- or immune-associated diseases and obesity and diabetes employing said compounds.

  提供了一些新型非类固醇化合物，其在治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节有关的疾病方面具有用途，包括炎症和免疫性疾病、肥胖和糖尿病，其结构为公式（I），其对映体、顺反异构体或其药学上可接受的盐或水合物，其中（Ia）为杂环或杂芳烃；J，Ja，E，F，G，Ma，M，Q，Za和Z的定义如本文所述。还提供了使用所述化合物治疗炎症或免疫相关疾病、肥胖和糖尿病的药物组合物和方法。
• Modulators of glucocorticoid receptor, AP-1, and/or NF-κB activity and use thereof
  申请人：Bristol-Myers Squibb Company

  公开号：US08067447B2

  公开（公告）日：2011-11-29

  Novel non-steroidal compounds are provided which are useful in treating diseases associated with modulation of the glucocorticoid receptor, and/or AP-1, and/or NF-κB activity including inflammatory and immune diseases, obesity and diabetes having the structure of formula (I), its enantiomers, diastereomers, or a pharmaceutically-acceptable salt, or hydrate, thereof, wherein (Ia) is heterocycle or heteroaryl; J, Ja, E, F, G, Ma, M, Q, Za and Z are as defined herein. Also provided are pharmaceutical compositions and methods of treating inflammatory- or immune-associated diseases and obesity and diabetes employing said compounds.

  提供了新型非甾体化合物，其有助于治疗与糖皮质激素受体、AP-1和/或NF-κB活性调节相关的疾病，包括炎症和免疫性疾病、肥胖和糖尿病，其结构式（I），其对映体，二对映异构体或其药学上可接受的盐或水合物，其中（Ia）是杂环或杂环芳基；J，Ja，E，F，G，Ma，M，Q，Za和Z如本文所定义。还提供了制药组合物和使用该化合物治疗炎症或免疫相关疾病以及肥胖和糖尿病的方法。
• WO2008/57856
  申请人：——

  公开号：——

  公开（公告）日：——
• MODULATORS OF GLUCOCORTICOID RECEPTOR, AP-1 AND/OR NF-KAPPAB ACTIVITY AND USE THEREOF
  申请人：Bristol-Myers Squibb Company

  公开号：EP2094692B1

  公开（公告）日：2012-11-28