5-phenanthren-2-yl-isoxazole-3-carboxylic acid | 1314023-85-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 菲及其衍生物
• 英文名称: 5-phenanthren-2-yl-isoxazole-3-carboxylic acid
• CAS: 1314023-85-2
• 化学式: C₁₈H₁₁NO₃
• 分子量: 289.29
• InChiKey: GKPYCHIMYXWVCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  22.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  63.33
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  5-phenanthren-2-yl-isoxazole-3-carboxylic acid 、 3-苯基-1-丙胺 在 1-羟基苯并三唑 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.75h， 以72%的产率得到5-(phenanthr-2-yl)-N-(3-phenylpropyl)isoxazole-5-carboxamide
  参考文献：
  名称：

  New FAAH inhibitors based on 3-carboxamido-5-aryl-isoxazole scaffold that protect against experimental colitis

  摘要：

  Growing evidence suggests a role for the endocannabinoid (EC) system, in intestinal inflammation and compounds inhibiting anandamide degradation offer a promising therapeutic option for the treatment of inflammatory bowel diseases. In this paper, we report the first series of carboxamides derivatives possessing FAAH inhibitory activities. Among them, compound 39 displayed significant inhibitory FAAH activity (IC50 = 0.088 mu M) and reduced colitis induced by intrarectal administration of TNBS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.057
• 作为产物：
  描述：

  2-hydroxy-4-oxo-4-(2-phenanthryl)but-2-enoic acid ethyl ester 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 乙醇 为溶剂， 反应 26.0h， 生成 5-phenanthren-2-yl-isoxazole-3-carboxylic acid
  参考文献：
  名称：

  New FAAH inhibitors based on 3-carboxamido-5-aryl-isoxazole scaffold that protect against experimental colitis

  摘要：

  Growing evidence suggests a role for the endocannabinoid (EC) system, in intestinal inflammation and compounds inhibiting anandamide degradation offer a promising therapeutic option for the treatment of inflammatory bowel diseases. In this paper, we report the first series of carboxamides derivatives possessing FAAH inhibitory activities. Among them, compound 39 displayed significant inhibitory FAAH activity (IC50 = 0.088 mu M) and reduced colitis induced by intrarectal administration of TNBS. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.04.057