4-[5-cyano-2-(4-fluorophenyl)-1H-indol-3-yl]butanoic acid | 475287-14-0

• 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: 4-[5-cyano-2-(4-fluorophenyl)-1H-indol-3-yl]butanoic acid
• CAS: 475287-14-0
• 化学式: C₁₉H₁₅FN₂O₂
• 分子量: 322.339
• InChiKey: OORIBYAWEGARTK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  76.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[5-cyano-2-(4-fluorophenyl)-1H-indol-3-yl]butanoic acid 在 4-二甲氨基吡啶 、 磺酰胺 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 N-(aminosulfonyl)-4-[5-cyano-2-(4-fluorophenyl)-1H-indol-3-yl]butanamide
  参考文献：
  名称：

  Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor

  摘要：

  A series of novel acylsulfonamide, acylsulfamide, and sulfonylurea bioisosteres of carboxylic acids were prepared as CXCR2 antagonists. Structure-activity relationships are reported for these series. One potent orally bioavailable inhibitor had excellent PK properties and was active in a lung injury model in hyperoxia-exposed newborn rats. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.127
• 作为产物：
  描述：

  4-[5-bromo-2-(4-fluorophenyl)-1H-indol-3-yl]butanoic acid 、 氰化亚铜 以 N-甲基吡咯烷酮 为溶剂， 生成 4-[5-cyano-2-(4-fluorophenyl)-1H-indol-3-yl]butanoic acid
  参考文献：
  名称：

  Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor

  摘要：

  A series of novel acylsulfonamide, acylsulfamide, and sulfonylurea bioisosteres of carboxylic acids were prepared as CXCR2 antagonists. Structure-activity relationships are reported for these series. One potent orally bioavailable inhibitor had excellent PK properties and was active in a lung injury model in hyperoxia-exposed newborn rats. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2008.01.127

文献信息

• 5-cyano-1h-indole derivatives as antagonist of the inerleukine-8 receptors
  申请人：Barth Martine

  公开号：US20050100902A1

  公开（公告）日：2005-05-12

  The present invention relates to derivatives of 5-cyano-1H-indole of formula (I): in which R 1 , R 2 , X and n are as defined in claim 1, as well as to their pharmaceutically acceptable salts, solvates and hydrates. Pharmaceutical compositions containing them, as well as their use for the preparation of medicaments intended for the preventative or curative treatment of illnesses which are dependent upon the activation of the interleukin CXCR2 receptor and of the chemokines of the same family, are also subjects of the invention.

  本发明涉及式（I）的 5-氰基-1H-吲哚衍生物： 其中 R 1 , R 2 、X 和 n 如权利要求 1 所定义，以及它们的药学上可接受的盐、溶液和水合物。含有它们的药物组合物，以及它们在制备用于预防或治疗依赖于白细胞介素 CXCR2 受体和同族趋化因子激活的疾病的药物中的用途，也是本发明的主题。
• Carboxylic acid bioisosteres acylsulfonamides, acylsulfamides, and sulfonylureas as novel antagonists of the CXCR2 receptor
  作者：Michael P. Winters、Carl Crysler、Nalin Subasinghe、Declan Ryan、Lynette Leong、Shuyuan Zhao、Robert Donatelli、Edward Yurkow、Marie Mazzulla、Lisa Boczon、Carl L. Manthey、Christopher Molloy、Holly Raymond、Lynne Murray、Laura McAlonan、Bruce Tomczuk

  DOI：10.1016/j.bmcl.2008.01.127

  日期：2008.3

  A series of novel acylsulfonamide, acylsulfamide, and sulfonylurea bioisosteres of carboxylic acids were prepared as CXCR2 antagonists. Structure-activity relationships are reported for these series. One potent orally bioavailable inhibitor had excellent PK properties and was active in a lung injury model in hyperoxia-exposed newborn rats. (C) 2008 Elsevier Ltd. All rights reserved.