4-(N-acetylamino)-6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran | 226922-87-8

• 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: 4-(N-acetylamino)-6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran
• 英文别名: N-(6-bromo-2,2-dimethyl-3,4-dihydrochromen-4-yl)acetamide
• CAS: 226922-87-8
• 化学式: C₁₃H₁₆BrNO₂
• 分子量: 298.18
• InChiKey: FLDHNDTWLLJDJF-UHFFFAOYSA-N

物化性质

• 沸点：
  414.2±45.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(N-acetylamino)-6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran 在 盐酸 作用下， 生成 6-溴-3,4-二氢-2,2-二甲基-2H-1-苯并吡喃-4-胺
  参考文献：
  名称：

  4,6-Disubstituted 2,2-Dimethylchromans Structurally Related to the K_ATP Channel Opener Cromakalim: Design, Synthesis, and Effect on Insulin Release and Vascular Tone

  摘要：

  Five series (ureas, thioureas, carbamates, sulfonylureas, and amides) of 4,6-disubstituted-2,2dimethylchromans structurally related to cromakalim were prepared and evaluated, as putative ATP-sensitive potassium channel activators, on rat pancreatic islets and rat aorta rings. The biological data indicate that most compounds were, like the reference molecule cromakalim, more active on the vascular smooth muscle tissue (myorelaxant effect on 30 mM KCl induced contractions of rat aorta rings) than on the pancreatic tissue (inhibition of 16.7 mM glucose induced insulin release from rat pancreatic islets). However, some drugs (8h, 8i, 9f, 9g, 9h, and 9i) markedly inhibited insulin release and exhibited an activity equivalent or greater than that of diazoxide. Compounds 9h and 9i were also found to be more active on pancreatic beta-cells than on vascular smooth muscle cells. Last, the amide 6b was selected in order to examine its mechanism of action on vascular smooth muscle cells. Pharmacological results suggest that the compound acted as a K-ATP channel opener. In conclusion, the present data indicate that appropriate structural modifications can generate dimethylchromans with pharmacological profiles different from that of cromakalim.

  DOI：

  10.1021/jm040789e
• 作为产物：
  描述：

  6-溴-2,2-二甲基-4-二氢色原酮 在 sodium tetrahydroborate 、 硫酸 作用下， 以 甲醇 为溶剂， 生成 4-(N-acetylamino)-6-bromo-3,4-dihydro-2,2-dimethyl-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

文献信息

• Synthesis and Pharmacological Evaluation of K&lt;SUB&gt;ATP&lt;/SUB&gt;-channel Openers Related to Cromakalim: Introduction of Arylsulphonylurea Moieties
  作者：S. Khelili、P. Lebrun、J. Delarge、B. Pirotte

  DOI：10.1211/146080899128734587

  日期：1999.3.1
• 4,6-Disubstituted 2,2-Dimethylchromans Structurally Related to the K_ATP Channel Opener Cromakalim: Design, Synthesis, and Effect on Insulin Release and Vascular Tone
  作者：Sophie Sebille、Pascal de Tullio、Bénédicte Becker、Marie-Hélène Antoine、Stéphane Boverie、Bernard Pirotte、Philippe Lebrun

  DOI：10.1021/jm040789e

  日期：2005.1.1

  Five series (ureas, thioureas, carbamates, sulfonylureas, and amides) of 4,6-disubstituted-2,2dimethylchromans structurally related to cromakalim were prepared and evaluated, as putative ATP-sensitive potassium channel activators, on rat pancreatic islets and rat aorta rings. The biological data indicate that most compounds were, like the reference molecule cromakalim, more active on the vascular smooth muscle tissue (myorelaxant effect on 30 mM KCl induced contractions of rat aorta rings) than on the pancreatic tissue (inhibition of 16.7 mM glucose induced insulin release from rat pancreatic islets). However, some drugs (8h, 8i, 9f, 9g, 9h, and 9i) markedly inhibited insulin release and exhibited an activity equivalent or greater than that of diazoxide. Compounds 9h and 9i were also found to be more active on pancreatic beta-cells than on vascular smooth muscle cells. Last, the amide 6b was selected in order to examine its mechanism of action on vascular smooth muscle cells. Pharmacological results suggest that the compound acted as a K-ATP channel opener. In conclusion, the present data indicate that appropriate structural modifications can generate dimethylchromans with pharmacological profiles different from that of cromakalim.