6,7,8,9-Tetrahydropyrido[1,2-a]indol-7-yl methanesulfonate | 1218918-63-8

• 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: 6,7,8,9-Tetrahydropyrido[1,2-a]indol-7-yl methanesulfonate
• 英文别名: 6,7,8,9-tetrahydropyrido[1,2-a]indol-7-yl methanesulfonate
• CAS: 1218918-63-8
• 化学式: C₁₃H₁₅NO₃S
• 分子量: 265.333
• InChiKey: GTLWXIFCXHUNAR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  56.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6,7,8,9-Tetrahydropyrido[1,2-a]indol-7-yl methanesulfonate 在 4-二甲氨基吡啶 、 sodium azide 、 palladium on carbon 、 氢气 、 sodium hydride 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 31.0h， 生成 (+/-) 4-fluoro-N-methyl-N-(6,7,8,9-tetrahydropyrido[1,2-a]indol-7-yl)benzenesulfonamide
  参考文献：
  名称：

  New indole amide derivatives as potent CRTH2 receptor antagonists

  摘要：

  A new series of indole amide acting as hCRTH2 receptor ligands had been explored and are described herein. Several amide derivatives displaying low nanomolar activity in hCRTH2 binding and whole blood assays were identified. They were found to behave as a full antagonists, exhibiting good selectivity over related prostaglandin receptors. Also, prototypical compounds in this novel series which displayed acceptable CYP profiles and were orally bioavailable in rats were identified. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.085
• 作为产物：
  描述：

  1H-吲哚-2-甲醛 在 sodium tetrahydroborate 、 palladium on carbon 、 potassium tert-butylate 、 氢气 、 silica gel 、 caesium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -40.0~60.0 ℃ 、101.33 kPa 条件下， 反应 65.5h， 生成 6,7,8,9-Tetrahydropyrido[1,2-a]indol-7-yl methanesulfonate
  参考文献：
  名称：

  New indole amide derivatives as potent CRTH2 receptor antagonists

  摘要：

  A new series of indole amide acting as hCRTH2 receptor ligands had been explored and are described herein. Several amide derivatives displaying low nanomolar activity in hCRTH2 binding and whole blood assays were identified. They were found to behave as a full antagonists, exhibiting good selectivity over related prostaglandin receptors. Also, prototypical compounds in this novel series which displayed acceptable CYP profiles and were orally bioavailable in rats were identified. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.03.085

文献信息

• [EN] INDOLE DERIVATIVES AS CRTH2 RECEPTOR ANTAGONISTS<br/>[FR] DÉRIVÉS D'INDOLE UTILISABLES EN TANT QU'ANTAGONISTES DU RÉCEPTEUR CRTH2
  申请人：MERCK FROSST CANADA LTD

  公开号：WO2010031182A1

  公开（公告）日：2010-03-25

  The compound (+) 7R-[[(4-fluorophenyl)sulfonyl](methyl)ammo]-6,7,8,9-tetrahydropyrido[1,2-a]mdol-10-yl}acetic acid and pharmaceutically acceptable salts thereof are antagonists of the PGD2 receptor, CRTH2, and as such are useful in the treatment and/or prevention of CRTH2-meidated diseases such as asthma.

  (+)7R-[[(4-氟苯基)磺酰](甲基)氨基]-6,7,8,9-四氢吡啶并[1,2-a]吲哚-10-基}乙酸及其药用盐是PGD2受体CRTH2的拮抗剂，因此在治疗和/或预防CRTH2介导的疾病如哮喘中是有用的。
• TRICYCLIC COMPOUNDS AS ANTAGONISTS OF PROSTAGLANDIN D2 RECEPTORS
  申请人：Stearns Brian Andrew

  公开号：US20120004233A1

  公开（公告）日：2012-01-05

  Described herein are antagonists of PGD 2 receptors. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such antagonists of PGD 2 receptors, alone and in combination with other compounds, for treating respiratory, cardiovascular, and other PGD 2 -dependent or PGD 2 -mediated conditions or diseases.

  本文描述了PGD2受体拮抗剂。还描述了包括本文所述化合物的制药组合物和药物，以及使用这些PGD2受体拮抗剂的方法，单独或与其他化合物结合，用于治疗呼吸系统、心血管系统和其他PGD2依赖性或PGD2介导的疾病或病症。
• WO2007/19675
  申请人：——

  公开号：——

  公开（公告）日：——
• New indole amide derivatives as potent CRTH2 receptor antagonists
  作者：Helmi Zaghdane、Michael Boyd、John Colucci、Daniel Simard、Carl Berthelette、Yves Leblanc、Zhaoyin Wang、Robert Houle、Jean François Lévesque、Carmela Molinaro、Martine Hamel、Rino Stocco、Nicole Sawyer、Susan Sillaots、François Gervais、Michel Gallant

  DOI：10.1016/j.bmcl.2011.03.085

  日期：2011.6

  A new series of indole amide acting as hCRTH2 receptor ligands had been explored and are described herein. Several amide derivatives displaying low nanomolar activity in hCRTH2 binding and whole blood assays were identified. They were found to behave as a full antagonists, exhibiting good selectivity over related prostaglandin receptors. Also, prototypical compounds in this novel series which displayed acceptable CYP profiles and were orally bioavailable in rats were identified. (C) 2011 Elsevier Ltd. All rights reserved.