4α-O-(2'',3''-bis(benzoxycarbonylamino)propanoyl)-podophyllotoxin | 1443511-06-5

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 木脂素内酯
• 英文名称: 4α-O-(2'',3''-bis(benzoxycarbonylamino)propanoyl)-podophyllotoxin
• 英文别名: [(5R,5aR,8aR,9R)-8-oxo-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl] 2,3-bis(phenylmethoxycarbonylamino)propanoate
• CAS: 1443511-06-5
• 化学式: C₄₁H₄₀N₂O₁₃
• 分子量: 768.774
• InChiKey: WDXJDCWYVBMDRX-IPKVDBHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  175
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  4α-O-(2'',3''-bis(benzoxycarbonylamino)propanoyl)-podophyllotoxin 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 生成 4α-O-(2'',3''-diaminopropanoyl)podophyllotoxin
  参考文献：
  名称：

  Synthesis and anticancer activity of dichloroplatinum(II) complexes of podophyllotoxin

  摘要：

  A series of dichloroplatinum(II) complexes of podophyllotoxin (PPT) were prepared, and their cytotoxicity against sensitive (A-549, HeLa, HCT-8, Hep-G2, K562) and resistant (ADM/K562) cell lines were evaluated. Complex cis-[4 alpha-O-(2 '',3 ''-diaminopropanoyl)-podophyllotoxin] dichloride platinum(II) (12) displayed most potent cytotoxicity with IC50 value in the range 0.071-2.98 mu M. Complex 12 induces cell cycle arrest in the G(2)/M phase, and inhibits the formation of microtubules in HeLa cells. Furthermore, this complex exhibits potent DNA cleavage capabilities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.089
• 作为产物：
  描述：

  (+/-)-N,N'-dicarbobenzyloxy-2,3-diaminopropanoic acid 、 鬼臼毒素 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以1.05 g的产率得到4α-O-(2'',3''-bis(benzoxycarbonylamino)propanoyl)-podophyllotoxin
  参考文献：
  名称：

  Synthesis and anticancer activity of dichloroplatinum(II) complexes of podophyllotoxin

  摘要：

  A series of dichloroplatinum(II) complexes of podophyllotoxin (PPT) were prepared, and their cytotoxicity against sensitive (A-549, HeLa, HCT-8, Hep-G2, K562) and resistant (ADM/K562) cell lines were evaluated. Complex cis-[4 alpha-O-(2 '',3 ''-diaminopropanoyl)-podophyllotoxin] dichloride platinum(II) (12) displayed most potent cytotoxicity with IC50 value in the range 0.071-2.98 mu M. Complex 12 induces cell cycle arrest in the G(2)/M phase, and inhibits the formation of microtubules in HeLa cells. Furthermore, this complex exhibits potent DNA cleavage capabilities. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.04.089