N-(6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(3-cyanophenyl)-S-methylisothiourea | 1202523-62-3

• 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: N-(6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(3-cyanophenyl)-S-methylisothiourea
• 英文别名: methyl N'-(6-bromo-2,2-dimethyl-3,4-dihydrochromen-4-yl)-N-(3-cyanophenyl)carbamimidothioate
• CAS: 1202523-62-3
• 化学式: C₂₀H₂₀BrN₃OS
• 分子量: 430.368
• InChiKey: OJTPNKBZLKKMEM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  82.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  N-(6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(3-cyanophenyl)-S-methylisothiouronium hydroiodide 在 silica gel 作用下， 以 乙酸乙酯 、 Petroleum ether 为溶剂， 以0.041 g的产率得到N-(6-bromo-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(3-cyanophenyl)-S-methylisothiourea
  参考文献：
  名称：

  New R/S-3,4-dihydro-2,2-dimethyl-2H-1-benzopyrans as KATP channel openers: Modulation of the 4-position

  摘要：

  The present work aimed at exploring a series of diversely 4-arylthiourea-substituted R/S-3,4-dihydro-2,2-dimethyl- 6-halo-2H-1-benzopyrans structurally related to (+/-)-cromakalim. These new compounds were examined in vitro as putative potassium channel openers (PCOs) on rat pancreatic islets (inhibition of insulin release) as well as on rat aorta rings (relaxation of aorta ring) and their activity was compared to that of the reference K-ATP channel activators (+/-)-cromakalim, (+/-)-pinacidil, diazoxide and of previously reported cromakalim analogues. Structure-activity relationships indicated that the most pronounced inhibitory activity on the insulin secretory process was obtained with molecules bearing a strong metaor para-electron-withdrawing group (CN or NO2) on the phenyl ring of the arylthiourea moiety at the 4-position of the benzopyran nucleus (compounds 12-23). Among those, R/S-6-chloro-4-(4-cyanophenylaminothiocarbonylamino)-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (16) was found to be the most potent benzopyran-type inhibitor of insulin release ever described. Most of these original benzopyran derivatives show increased selectivity for pancreatic versus vascular tissue. Radioisotopic investigations indicated that these new compounds activated pancreatic KATP channels. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.041