N-(3-Cyano-phenyl)-2-{4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-adamantan-1-yl]-phenoxy}-acetamide | 1192322-70-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 四氢异喹啉
• 英文名称: N-(3-Cyano-phenyl)-2-{4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-adamantan-1-yl]-phenoxy}-acetamide
• 英文别名: N-(3-cyanophenyl)-2-[4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-1-adamantyl]phenoxy]acetamide
• CAS: 1192322-70-5
• 化学式: C₃₇H₃₉N₃O₅
• 分子量: 605.734
• InChiKey: AELBOLRAJBHJSP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  45
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  101
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  {4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-adamantan-1-yl]-phenoxy}-ethanoic acid 、 间氨基苯甲腈 在 sodium cyanide 、 1-丙基磷酸酐 、 三乙胺 作用下， 生成 N-(3-Cyano-phenyl)-2-{4-[3-(6,7-dimethoxy-3,4-dihydro-1H-isoquinoline-2-carbonyl)-adamantan-1-yl]-phenoxy}-acetamide
  参考文献：
  名称：

  A novel class of highly potent multidrug resistance reversal agents: Disubstituted adamantyl derivatives

  摘要：

  Novel disubstituted adamantyl derivatives were synthesized and evaluated in a P-glycoprotein dependent multidrug resistance cancer cell line. The hit to lead optimization provided potent MDR reversal agents. Some potent adamantyl derivatives were more than 10-fold more potent than verapamil without considerable intrinsic cytotoxicity. The 3-trifluorophenyl derivative 14f did not affect the metabolism of CYP450 3A4, whereas most of MDR revertants had a weak inhibitory effect. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.07.127

文献信息

• A novel class of highly potent multidrug resistance reversal agents: Disubstituted adamantyl derivatives
  作者：Kyung Hoon Min、Yan Xia、Eun Kyung Kim、Yinglan Jin、Navneet Kaur、Eun Seon Kim、Dae Kyong Kim、Hwa Young Jung、Yongseok Choi、Mi-Kyung Park、Yong Ki Min、Kiho Lee、Kyeong Lee

  DOI：10.1016/j.bmcl.2009.07.127

  日期：2009.9

  Novel disubstituted adamantyl derivatives were synthesized and evaluated in a P-glycoprotein dependent multidrug resistance cancer cell line. The hit to lead optimization provided potent MDR reversal agents. Some potent adamantyl derivatives were more than 10-fold more potent than verapamil without considerable intrinsic cytotoxicity. The 3-trifluorophenyl derivative 14f did not affect the metabolism of CYP450 3A4, whereas most of MDR revertants had a weak inhibitory effect. (C) 2009 Elsevier Ltd. All rights reserved.