(-)-2-[(4aS,8aR)-4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)octahydroquinoxalin-1(2H)-yl]-6,7-dimethoxyquinazolin-4-amine | 1174122-39-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: (-)-2-[(4aS,8aR)-4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)octahydroquinoxalin-1(2H)-yl]-6,7-dimethoxyquinazolin-4-amine
• 英文别名: cyclodoxazosin；[(4aR,8aS)-4-(4-amino-6,7-dimethoxyquinazolin-2-yl)-2,3,4a,5,6,7,8,8a-octahydroquinoxalin-1-yl]-(2,3-dihydro-1,4-benzodioxin-3-yl)methanone
• CAS: 1174122-39-4
• 化学式: C₂₇H₃₁N₅O₅
• 分子量: 505.574
• InChiKey: RZKGYUBITDXCBT-ZJWBFHOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  37
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2,3-二氢-1,4-苯并二英-2-碳酰氯 、 6,7-dimethoxy-2-cis-perhydro-1-quinoxalinyl-4-quinazolinamine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 生成 (-)-2-[(4aS,8aR)-4-(2,3-dihydro-1,4-benzodioxin-2-ylcarbonyl)octahydroquinoxalin-1(2H)-yl]-6,7-dimethoxyquinazolin-4-amine
  参考文献：
  名称：

  Doxazosin-Related α₁-Adrenoceptor Antagonists With Prostate Antitumor Activity

  摘要：

  Doxazosin analogues 1-3 and 1 a were synthesized and investigated at alpha(1)-adrenoceptors and PC-3, DU-145, and LNCaP human prostate cancer cells. Compound 1 (cyclodoxazosin) was a potent alpha(1B)-adrenoceptor antagonist displaying anti proliferative activity higher than that of doxazosin in cancer cells in vitro and in vivo, respectively. Because of its antitumor efficacy at low concentrations, lower apoptotic activity in NHDF vs tumor cells, and antiangiogenetic effect, 1 showed a better therapeutic profile relative to doxazosin.

  DOI：

  10.1021/jm8016046

文献信息

• Doxazosin-Related α₁-Adrenoceptor Antagonists With Prostate Antitumor Activity
  作者：Dario Giardinà、Daniele Martarelli、Gianni Sagratini、Piero Angeli、Dario Ballinari、Ugo Gulini、Carlo Melchiorre、Elena Poggesi、Pierluigi Pompei

  DOI：10.1021/jm8016046

  日期：2009.8.13

  Doxazosin analogues 1-3 and 1 a were synthesized and investigated at alpha(1)-adrenoceptors and PC-3, DU-145, and LNCaP human prostate cancer cells. Compound 1 (cyclodoxazosin) was a potent alpha(1B)-adrenoceptor antagonist displaying anti proliferative activity higher than that of doxazosin in cancer cells in vitro and in vivo, respectively. Because of its antitumor efficacy at low concentrations, lower apoptotic activity in NHDF vs tumor cells, and antiangiogenetic effect, 1 showed a better therapeutic profile relative to doxazosin.