2-methyl-3-(1-imidazolyl)-2,3-dihydro-6-carboxy-4H-1-benzopyran-4-ol | 85928-52-5

• 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: 2-methyl-3-(1-imidazolyl)-2,3-dihydro-6-carboxy-4H-1-benzopyran-4-ol
• 英文别名: 4-hydroxy-3-imidazol-1-yl-2-methyl-3,4-dihydro-2H-chromene-6-carboxylic acid
• CAS: 85928-52-5
• 化学式: C₁₄H₁₄N₂O₄
• 分子量: 274.276
• InChiKey: ZWARBBSBGDGGIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  84.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-methyl-3-(1-imidazolyl)-2,3-dihydro-6-carboxy-4H-1-benzopyran-4-ol 在 palladium on activated charcoal 盐酸 、 硫酸 、 氢气 、 溶剂黄146 作用下， 以 乙醇 、 溶剂黄146 为溶剂， 25.0~100.0 ℃ 、344.73 kPa 条件下， 反应 16.0h， 生成 (2R,3R)-3-Imidazol-1-yl-2-methyl-chroman-6-carboxylic acid; hydrochloride
  参考文献：
  名称：

  N-imidazolyl derivatives of the napththalene and chroman rings as thromboxane A2 synthase inhibitors

  摘要：

  A series of N-imidazol-1-yl derivatives of 1,2-dihydronaphthalene, 1,2,3,4-tetrahydronaphthalene, 2H-1-benzopyran and some related compounds were synthesized and tested as inhibitors of thromboxane A2 synthase in ex vivo experiments with orally treated rats. Some compounds showed good activity which was confirmed in experiments in vitro in rabbit whole blood. Some structural requirements for significant TxA2 synthase inhibitory activity are discussed. The selected 5,6-Dihydro-7-(H-1-imidazol-1-yl)-2-naphthalene-carboxylic acid (compound 7) was conformationally analysed using the Sybyl molecular model system in comparison with dazoxiben. Compound 7 was further pharmacologically investigated and on the basis of its interesting activities in vitro, ex vivo and in vivo and its low toxicity was selected for clinical investigation.

  DOI：

  10.1016/0223-5234(91)90103-t

文献信息

• US4492707A
  申请人：——

  公开号：US4492707A

  公开（公告）日：1985-01-08
• US4588738A
  申请人：——

  公开号：US4588738A

  公开（公告）日：1986-05-13