6-hydroxy-5-methyl<1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one | 79572-25-1

• 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: 6-hydroxy-5-methyl<1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one
• 英文别名: 6-hydroxy-5-methyl-2H-chromeno[2,3-d]triazol-9-one
• CAS: 79572-25-1
• 化学式: C₁₀H₇N₃O₃
• 分子量: 217.184
• InChiKey: CJKACXCDWARJGM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  88.1
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-hydroxy-5-methyl<1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one 在 potassium carbonate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.5h， 生成 6-[3-[4-[(4-chlorophenyl)methyl]piperazin-1-yl]propoxy]-5-methyl-2-tritylchromeno[2,3-d]triazol-9-one
  参考文献：
  名称：

  Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties

  摘要：

  Several N-benzylpiperazino derivatives of [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one and its 5-methyl homologue have been prepared and evaluated for H1-antihistamine activity on guinea pig ileum. The most potent compounds were also evaluated for their ability to stabilize mast cells in the rat passive peritoneal anaphylaxis (PPA) system and were shown to inhibit histamine release at concentrations below those required to inhibit extravasation, suggesting that this might be relevant to their antianaphylactic activity in this system. The compound tested with the most potent H1-antihistamine activity was 6-[3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy][1]benzopyrano[2,3- d]-1,2,3-triazol-9(1H)-one, 28, which had a pA2 of 9.1 against histamine on guinea pig ileum, comparable to that of mepyramine, and inhibited histamine release in the rat PPA system with an IC50 value of 5.4 X 10(-6) M.

  DOI：

  10.1021/jm00161a022
• 作为产物：
  描述：

  2-甲基-3-甲氧基苯酚 在 palladium on activated charcoal 磷酸酐 、 sodium hydroxide 、 甲烷磺酸 、 氢气 、 sodium hydride 、 乙硫醇 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0~115.0 ℃ 、6.89 MPa 条件下， 反应 31.0h， 生成 6-hydroxy-5-methyl<1>benzopyrano<2,3-d>-1,2,3-triazol-9(1H)-one
  参考文献：
  名称：

  对三唑的研究。7.抗过敏的9-氧代-1H，9H-苯并吡喃并[2，3-d] -v-三唑。

  摘要：

  通过环合适当的5-（芳氧基）-v-三唑-4-羧酸制备一系列少量化合物，并通过大鼠被动皮肤过敏反应（PCA）筛选评估其抗过敏活性。最有效的化合物是6-（甲氧基）-9-氧代-1H，9H-苯并吡喃并[2,3-d] -v-三唑及其5-甲基同系物，其效力比色甘酸二钠强十倍。二烷基衍生物，尤其是在C-5和C-6或C-6和C-7取代的那些，以及6-甲氧基化合物也是更有效的化合物。进一步评估了一种化合物6,7-二甲基-9-氧代-1H，9H-苯并吡喃并[2,3-d] -v-三唑，并经口服证明是有效的大鼠PCA抑制剂。

  DOI：

  10.1021/jm00356a025

文献信息

• BUCKLE, D. R.;OUTRED, D. J.;ROCKELL, C. J. M.;SMITH, H.;SPICER, B. A., J. MED. CHEM., 1983, 26, N 2, 251-254
  作者：BUCKLE, D. R.、OUTRED, D. J.、ROCKELL, C. J. M.、SMITH, H.、SPICER, B. A.

  DOI：——

  日期：——
• BUCKLE D. R.; ROCKELL C. J. M.; SMITH H.; SPICER B. A., J. MED. CHEM., 29,(1986) N 11, 2262-2267
  作者：BUCKLE D. R.、 ROCKELL C. J. M.、 SMITH H.、 SPICER B. A.

  DOI：——

  日期：——
• Studies on v-triazoles. 7. Antiallergic 9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazoles
  作者：Derek R. Buckle、D. James Outred、Caroline J. M. Rockell、Harry Smith、Barbara A. Spicer

  DOI：10.1021/jm00356a025

  日期：1983.2

  6-(mesyloxy)-9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazole and its 5-methyl homologue, which were some tenfold more potent than disodium cromoglycate. Dialkyl derivatives, especially those substituted at C-5 and C-6 or C-6 and C-7, and 6-methoxy compounds were also among the more potent compounds. One compound, 6,7-dimethyl-9-oxo-1H,9H-benzopyrano[2,3-d]-v-triazole, was further evaluated and shown to be

  通过环合适当的5-（芳氧基）-v-三唑-4-羧酸制备一系列少量化合物，并通过大鼠被动皮肤过敏反应（PCA）筛选评估其抗过敏活性。最有效的化合物是6-（甲氧基）-9-氧代-1H，9H-苯并吡喃并[2,3-d] -v-三唑及其5-甲基同系物，其效力比色甘酸二钠强十倍。二烷基衍生物，尤其是在C-5和C-6或C-6和C-7取代的那些，以及6-甲氧基化合物也是更有效的化合物。进一步评估了一种化合物6,7-二甲基-9-氧代-1H，9H-苯并吡喃并[2,3-d] -v-三唑，并经口服证明是有效的大鼠PCA抑制剂。
• Studies on 1,2,3-triazoles. 13. (Piperazinylalkoxy)-[1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-ones with combined H1-antihistamine and mast cell stabilizing properties
  作者：Derek R. Buckle、Caroline J. M. Rockell、Harry Smith、Barbara A. Spicer

  DOI：10.1021/jm00161a022

  日期：1986.11

  Several N-benzylpiperazino derivatives of [1]benzopyrano[2,3-d]-1,2,3-triazol-9(1H)-one and its 5-methyl homologue have been prepared and evaluated for H1-antihistamine activity on guinea pig ileum. The most potent compounds were also evaluated for their ability to stabilize mast cells in the rat passive peritoneal anaphylaxis (PPA) system and were shown to inhibit histamine release at concentrations below those required to inhibit extravasation, suggesting that this might be relevant to their antianaphylactic activity in this system. The compound tested with the most potent H1-antihistamine activity was 6-[3-[4-(4-chlorobenzyl)-1-piperazinyl]propoxy][1]benzopyrano[2,3- d]-1,2,3-triazol-9(1H)-one, 28, which had a pA2 of 9.1 against histamine on guinea pig ileum, comparable to that of mepyramine, and inhibited histamine release in the rat PPA system with an IC50 value of 5.4 X 10(-6) M.