4-(5-phenyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzoic acid | 1187209-20-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 4-(5-phenyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzoic acid
• 英文别名: Benzoic acid, 4-[1-[(4-methylphenyl)sulfonyl]-5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl]-；4-[1-(4-methylphenyl)sulfonyl-5-phenylpyrrolo[2,3-b]pyridin-3-yl]benzoic acid
• CAS: 1187209-20-6
• 化学式: C₂₇H₂₀N₂O₄S
• 分子量: 468.533
• InChiKey: WCTQIUMYFZZRQB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  97.6
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(5-phenyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzoic acid 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以1.13 g的产率得到4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)benzoic acid
  参考文献：
  名称：

  Design and synthesis of orally bioavailable serum and glucocorticoid-regulated kinase 1 (SGK1) inhibitors

  摘要：

  The lead serum and glucocorticoid-related kinase 1 (SGK1) inhibitors 4-(5-phenyl-1H-pyrrolo[2,3-b]pyridin-3-yl)benzoic acid (1) and {4-[5-(2-naphthalenyl)-1H-pyrrolo[2,3-b] pyridin-3-yl]phenyl}acetic acid (2) suffer from low DNAUC values in rat, due in part to formation and excretion of glucuronic acid conjugates. These PK/glucuronidation issues were addressed either by incorporating a substituent on the 3-phenyl ring ortho to the key carboxylate functionality of 1 or by substituting on the group in between the carboxylate and phenyl ring of 2. Three of these analogs have been identified as having good SGK1 inhibition potency and have DNAUC values suitable for in vivo testing. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.05.051
• 作为产物：
  描述：

  5-溴-3-碘-7-氮杂吲哚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 sodium hydride 、 potassium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 生成 4-(5-phenyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzoic acid
  参考文献：
  名称：

  Discovering novel 7-azaindole-based series as potent AXL kinase inhibitors

  摘要：

  AXL is a receptor tyrosine kinase that plays a key role in tumor growth and proliferation. The scientific community has validated AXL as therapeutic target in the treatment of cancers for several years now, and several AXL inhibitors have been developed but none of them are approved. In this context, we started to design new kinase inhibitors targeting AXL from the 7-azaindole scaffold well known to interact with the ATP binding site of the kinase. Focused screening and chemical diversification around 7-azaindole scaffold were developed, based on modeling studies and medicinal chemistry rational, leading to the discovery of a new family of hits with potent inhibitory activity against AXL. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2017.01.015
• 作为试剂：
  描述：

  二氯甲烷 、 3-溴-1-[(4-甲基苯基)磺酰基]-5-苯基-1H-吡咯并[2,3-b]吡啶 、 4-羧基苯硼酸 、 potassium carbonate 、 盐酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 氮气 、 乙酸乙酯 、 水 、 Sodium sulfate-III 、 4-(5-phenyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzoic acid 作用下， 以 水 、 dioxane-water 为溶剂， 反应 3.0h， 生成 4-(5-phenyl-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-3-yl)-benzoic acid
  参考文献：
  名称：

  1H-Pyrrolo[2,3-B]Pyridnes

  摘要：

  本文描述了用作SGK-1激酶抑制剂的吡咯并[2,3-b]吡啶衍生物。本发明还描述了含有吡咯并[2,3-b]吡啶衍生物的制药组合物以及使用吡咯并[2,3-b]吡啶衍生物和其制药组合物治疗由SGK-1介导的疾病的方法。

  公开号：

  US20090233955A1

文献信息

• 1H-Pyrrolo[2,3-B]Pyridines
  申请人：Frazee James S.

  公开号：US20120238588A1

  公开（公告）日：2012-09-20

  Derivatives of pyrrolo[2,3-b]pyridine which are useful as SGK-1 kinase inhibitors are described herein. The invention described herein also describes pharmaceutical compositions containing derivatives of pyrrolo[2,3-b]pyridine and methods of using pyrrolo[2,3-b]pyridine derivatives and pharmaceutical compositions thereof in the treatment of diseases mediated by SGK-1.

  本文描述了作为SGK-1激酶抑制剂有用的吡咯[2,3-b]吡啶衍生物。本发明还描述了含有吡咯[2,3-b]吡啶衍生物的制药组合物以及使用吡咯[2,3-b]吡啶衍生物和制药组合物治疗由SGK-1介导的疾病的方法。
• WO2006/63167
  申请人：——

  公开号：——

  公开（公告）日：——
• 1H-PYRROLO[2,3-BETA]PYRIDINES
  申请人：SMITHKLINE BEECHAM CORPORATION

  公开号：EP1828180A1

  公开（公告）日：2007-09-05
• [EN] 1H-PYRROLO[2,3-B]PYRIDINES<br/>[FR] 1H -PYRROLO[2,3-B]PYRIDINES
  申请人：SMITHKLINE BEECHAM CORP

  公开号：WO2006063167A1

  公开（公告）日：2006-06-15

  [EN] Derivatives of pyrrolo[2,3-b]pyridine which are useful as SGK-1 kinase inhibitors are described herein. The invention described herein also describes pharmaceutical compositions containing derivatives of pyrrolo[2,3-b]pyridine and methods of using pyrrolo[2,3-b]pyridine derivatives and pharmaceutical compositions thereof in the treatment of diseases mediated by SGK-1.
  [FR] L'invention concerne des dérivés de pyrrolo[2,3-b]pyridine utiles comme inhibiteurs de kinase SGK-1. Cette invention concerne également des compositions pharmaceutiques renfermant des dérivés de pyrrolo[2,3-b]pyridine et des méthodes d'utilisation de dérivés de pyrrolo[2,3-b]pyridine et de leurs compositions dans le traitement de maladies induites par SGK-1.