6-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol | 226922-89-0

• 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-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol
• 英文别名: 6-amino-2,2-dimethyl-3,4-dihydrochromen-4-ol
• CAS: 226922-89-0
• 化学式: C₁₁H₁₅NO₂
• 分子量: 193.246
• InChiKey: FNWFVHPYOCTQHB-UHFFFAOYSA-N

物化性质

• 沸点：
  340.7±42.0 °C(Predicted)
• 密度：
  1.171±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.86
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  55.48
• 氢给体数：
  2.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  6-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol 在 盐酸 、 过氧乙酸 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 反应 11.33h， 生成 4-(benzenesulphonylaminocarbonylamino)3,4-dihydro-2,2-dimethyl-6-nitro-2H-1-benzopyran
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of K<SUB>ATP</SUB>-channel Openers Related to Cromakalim: Introduction of Arylsulphonylurea Moieties

  摘要：

  DOI：

  10.1211/146080899128734587
• 作为产物：
  描述：

  4'-甲氧基乙酰苯胺 在 四氢吡咯 、 sodium hydroxide 、 sodium tetrahydroborate 、 三氯化铝 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 6-amino-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-ol
  参考文献：
  名称：

  Synthesis and Pharmacological Evaluation of K<SUB>ATP</SUB>-channel Openers Related to Cromakalim: Introduction of Arylsulphonylurea Moieties

  摘要：

  DOI：

  10.1211/146080899128734587

文献信息

• Identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives as potassium channel activators and anti-inflammatory agents
  作者：Mohsina Bano、Kuldipsinh P. Barot、Shailesh V. Jain、Manjunath D. Ghate

  DOI：10.1007/s00044-015-1344-6

  日期：2015.7

  The present study described the design, synthesis and identification of 3-hydroxy-4[3,4-dihydro-3-oxo-2H-1,4-benzoxazin-4-yl]-2,2-dimethyldihydro-2H-benzopyran derivatives. Their biological activity was tested for K-ATP channel opener as antihypertensives, COX-1 and COX-2 activity. The results were compared with the activity of cromakalim, ibuprofen and celecoxib. The study aimed at exploring the influence of introduction of a benzoxazine substituent at position 6 of various derivatives of benzopyrans in order to improve biological activity. Several compounds were found to be equipotent or even more potent than cromakalim. Out of these nitro-substituted benzopyrans, nitro substitution at benzoxazino group possessed potent antihypertensive activity in the R/S isomers. With amino derivatives, activity remains constant when compared with standard cromakalim. Similarly, compounds 17b, 17c, 17e and 17h have exhibited around 40 % inhibition of COX-1 as compared to the inhibition of COX-2. Only two compounds 17g and 17i exhibited effective inhibition more than 50 % of COX-2 compared with the inhibition of COX-1 at a concentration of 0.3 mg/ml.