8-bromo-6-chlorochroman-4-one O-methyl oxime | 890839-49-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 8-bromo-6-chlorochroman-4-one O-methyl oxime
• CAS: 890839-49-3
• 化学式: C₁₀H₉BrClNO₂
• 分子量: 290.544
• InChiKey: RYGSPJFCFMROOV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.24
• 重原子数：
  15.0
• 可旋转键数：
  1.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  30.82
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  8-bromo-6-chlorochroman-4-one O-methyl oxime 在 tris-(dibenzylideneacetone)dipalladium(0) 、 palladium 10% on activated carbon 、 氨 、 氢气 、 R-(+)-1,1'-联萘-2,2'-双二苯膦 、 sodium t-butanolate 作用下， 以 1,4-二氧六环 、 甲醇 为溶剂， 50.0~170.0 ℃ 、413.7 kPa 条件下， 反应 18.5h， 生成 8-(piperidin-1-yl)chroman-4-amine
  参考文献：
  名称：

  Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists

  摘要：

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.056
• 作为产物：
  描述：

  6-氯-4-二氢色原酮 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 硫酸 作用下， 反应 27.0h， 生成 8-bromo-6-chlorochroman-4-one O-methyl oxime
  参考文献：
  名称：

  Chroman and tetrahydroquinoline ureas as potent TRPV1 antagonists

  摘要：

  Novel chroman and tetrahydroquinoline ureas were synthesized and evaluated for their activity as TRPV1 antagonists. It was found that aryl substituents on the 7- or 8-position of both bicyclic scaffolds imparted the best in vitro potency at TRPV1. The most potent chroman ureas were assessed in chronic and acute pain models, and compounds with the ability to cross the blood-brain barrier were shown to be highly efficacious. The tetrahydroquinoline ureas were found to be potent CYP3A4 inhibitors, but replacement of bulky substituents at the nitrogen atom of the tetrahydroisoquinoline moiety with small groups such as methyl can minimize the inhibition. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.01.056

文献信息

• Chromanylurea compounds that inhibit vanilloid receptor subtype 1 (VR1) receptor and uses thereof
  申请人：Gomtsyan Arthur

  公开号：US20060128689A1

  公开（公告）日：2006-06-15

  Compounds that are antagonists of the VR1 receptor, having formula (I) or a pharmaceutically acceptable salt, prodrug, or salt of a prodrug thereof, wherein A 1 , A 2 , A 3 , A 4 , R 7 , R 8 , R 9 , X, Y, Z, L, n, and m, are as defined herein, and are useful in disorders prevented or ameliorated by inhibiting the VR1 receptor.

  对VR1受体拮抗剂，其化学式为(I)或其药用可接受的盐、前药或前药的盐，其中A1、A2、A3、A4、R7、R8、R9、X、Y、Z、L、n和m的定义如本文所述，并且在通过抑制VR1受体预防或改善的疾病中具有用处。