3-demethoxycarbonyl-3-(4'-methoxybenzoylamino)methylvinorelbine | 1415687-27-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 3-demethoxycarbonyl-3-(4'-methoxybenzoylamino)methylvinorelbine
• 英文别名: methyl (12S,14R)-12-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-[[(4-methoxybenzoyl)amino]methyl]-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-16-ethyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaene-12-carboxylate
• CAS: 1415687-27-2
• 化学式: C₅₂H₆₁N₅O₈
• 分子量: 884.085
• InChiKey: XGBCJYWRRCXFRC-RYKMDJAISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  65
• 可旋转键数：
  12
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  146
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  methyl (13S,15R)-13-[(1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-10-hydroxy-5-methoxy-10-[[(4-methoxybenzoyl)amino]methyl]-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraen-4-yl]-17-ethyl-1,11-diazatetracyclo[13.3.1.04,12.05,10]nonadeca-4(12),5,7,9,16-pentaene-13-carboxylate 在 N-溴代丁二酰亚胺(NBS) 、 二乙胺 、 三氟乙酸 、 silver tetrafluoroborate 作用下， 以 二氯甲烷 、 四氢呋喃 、 水 为溶剂， 反应 3.0h， 生成 3-demethoxycarbonyl-3-(4'-methoxybenzoylamino)methylvinorelbine
  参考文献：
  名称：

  Synthesis and structure–activity relationship studies of cytotoxic vinorelbine amide analogues

  摘要：

  A series of 3-demethoxycarbonyl-3-acylamide methyl vinorelbine derivatives (compounds 7a-7z) were designed, synthesized, and evaluated for their inhibition activities against human non-small cell lung cancer cell line (A549). Most of the amide derivatives exhibited potent cytotoxicity, with the size of the introduced substituents being the foremost factor in determining the resultant cytotoxic activity. Test results in vivo against nude mice bearing A549 xenografts indicated that 7y showed comparable activities compared to the parent NVB. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.10.024