2-pyridin-3-yl-1H-indole-3-carbonitrile

• 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-pyridin-3-yl-1H-indole-3-carbonitrile
• 化学式: C₁₄H₉N₃
• 分子量: 219.246
• InChiKey: DSPUSSUXDINQSS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 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：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-pyridin-3-yl-1H-indole-3-carbonitrile 在 N-氯代丁二酰亚胺 、 sodium hydride 作用下， 以 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 49.5h， 生成 6-chloro-2-pyridin-3-yl-1-methyl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Discovery of N-[5-(6-Chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-ethanesulfonamide, a Cortisol-Sparing CYP11B2 Inhibitor that Lowers Aldosterone in Human Subjects

  摘要：

  Human clinical studies conducted with LCI699 established aldosterone synthase (CYP11B2) inhibition as a promising novel mechanism to lower arterial blood pressure. However, LCI699's low CYP11B1/CYP11B2 selectivity resulted in blunting of adrenocorticotropic hormone-stimulated cortisol secretion. This property of LCI699 prompted its development in Cushing's disease, but limited more extensive clinical studies in hypertensive populations, and provided an impetus for the search for cortisol-sparing CYP11B2 inhibitors. This paper summarizes the discovery, pharmacokinetics, and pharmacodynamic data in predinical species and human subjects of the selective CYP11B2 inhibitor 8.

  DOI：

  10.1021/acs.jmedchem.5b01545
• 作为产物：
  描述：

  2-氨基苯乙腈 在 sodium hydride 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 mineral oil 为溶剂， 反应 34.0h， 生成 2-pyridin-3-yl-1H-indole-3-carbonitrile
  参考文献：
  名称：

  Discovery of N-[5-(6-Chloro-3-cyano-1-methyl-1H-indol-2-yl)-pyridin-3-ylmethyl]-ethanesulfonamide, a Cortisol-Sparing CYP11B2 Inhibitor that Lowers Aldosterone in Human Subjects

  摘要：

  Human clinical studies conducted with LCI699 established aldosterone synthase (CYP11B2) inhibition as a promising novel mechanism to lower arterial blood pressure. However, LCI699's low CYP11B1/CYP11B2 selectivity resulted in blunting of adrenocorticotropic hormone-stimulated cortisol secretion. This property of LCI699 prompted its development in Cushing's disease, but limited more extensive clinical studies in hypertensive populations, and provided an impetus for the search for cortisol-sparing CYP11B2 inhibitors. This paper summarizes the discovery, pharmacokinetics, and pharmacodynamic data in predinical species and human subjects of the selective CYP11B2 inhibitor 8.

  DOI：

  10.1021/acs.jmedchem.5b01545

文献信息

• ORGANIC COMPOUNDS
  申请人：Adams Christopher

  公开号：US20110082129A1

  公开（公告）日：2011-04-07

  The present invention provides novel organic compounds of Formula I: methods of use, and pharmaceutical compositions thereof.

  本发明提供了化合物I的新型有机化合物，使用方法和其药物组成物。
• Organic compounds
  申请人：Novartis AG

  公开号：US08030334B2

  公开（公告）日：2011-10-04

  The present invention provides novel organic compounds of Formula I: methods of use, and pharmaceutical compositions thereof.

  本发明提供了新型有机化合物I的方法：使用方法和药物组成物。
• [EN] ORGANIC COMPOUNDS<br/>[FR] COMPOSÉS ORGANIQUES
  申请人：NOVARTIS AG

  公开号：WO2009156462A3

  公开（公告）日：2010-05-27
• Efficient solid-phase synthesis of 2,3-substituted indoles
  作者：Dean A Wacker、Padmaja Kasireddy

  DOI：10.1016/s0040-4039(02)01025-0

  日期：2002.7

  The development of the solid-phase version of the modified Madelung indole synthesis is reported. The chemistry was initiated with the reductive amination of Bal resin using an ortho substituted aniline. The resin bound aniline was acylated with a variety of acid chlorides followed by cyclization with base to provide the desired indole after TFA-promoted cleavage from the resin. (C) 2002 Elsevier Science Ltd. All rights reserved.
• US8030334B2
  申请人：——

  公开号：US8030334B2

  公开（公告）日：2011-10-04