8-Chloro-2-thiophen-3-yl-5-oxa-1,3,3a-triaza-cyclopenta[a]naphthalen-4-one

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 芳基卤化物
• 英文名称: 8-Chloro-2-thiophen-3-yl-5-oxa-1,3,3a-triaza-cyclopenta[a]naphthalen-4-one
• 英文别名: 9-Chloro-2-thiophen-3-yl-[1,2,4]triazolo[1,5-c][1,3]benzoxazin-5-one
• 化学式: C₁₃H₆ClN₃O₂S
• 分子量: 303.729
• InChiKey: OYEGDCHEZJHTAL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  20
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  85.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  三光气 、 4-Chloro-2-(5-thiophen-3-yl-2H-[1,2,4]triazol-3-yl)-phenol 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 以86%的产率得到8-Chloro-2-thiophen-3-yl-5-oxa-1,3,3a-triaza-cyclopenta[a]naphthalen-4-one
  参考文献：
  名称：

  Synthesis of Some 2-Aryl-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones as Tools To Define the Essential Pharmacophoric Descriptors of a Benzodiazepine Receptor Ligand

  摘要：

  The synthesis and benzodiazepine receptor (BZR) affinity of some 1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones, 2-22, are reported. Compounds 2-22 are devoid of the proton donor group, which according to a BZR schematic model was one of the pharmacophoric descriptors for receptor-ligand interaction. The binding data show that 2-(2-fluorophenyl)-9-chloro-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-one (12) and some other compounds display nanomolar BZR affinity, indicating that the hydrogen donor group is not essential for the anchoring of 6,6,5-tricyclic systems to the BZR but only affects the potency of a ligand.

  DOI：

  10.1021/jm00012a020

文献信息

• Synthesis of Some 2-Aryl-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones as Tools To Define the Essential Pharmacophoric Descriptors of a Benzodiazepine Receptor Ligand
  作者：Daniela Catarzi、Lucia Cecchi、Vittoria Colotta、Guido Filacchioni、Flavia Varano、Claudia Martini、Laura Giusti、Antonio Lucacchini

  DOI：10.1021/jm00012a020

  日期：1995.6

  The synthesis and benzodiazepine receptor (BZR) affinity of some 1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-ones, 2-22, are reported. Compounds 2-22 are devoid of the proton donor group, which according to a BZR schematic model was one of the pharmacophoric descriptors for receptor-ligand interaction. The binding data show that 2-(2-fluorophenyl)-9-chloro-1,2,4-triazolo[1,5-c][1,3]benzoxazin-5-one (12) and some other compounds display nanomolar BZR affinity, indicating that the hydrogen donor group is not essential for the anchoring of 6,6,5-tricyclic systems to the BZR but only affects the potency of a ligand.