4β-N-[2'',3''-bis(tert-butoxycarbonylamino)propanoyl]-4'-O-demethyl-podophyllotoxin | 1443511-08-7

• 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: 4β-N-[2'',3''-bis(tert-butoxycarbonylamino)propanoyl]-4'-O-demethyl-podophyllotoxin
• 英文别名: tert-butyl N-[1-[[(5S,5aS,8aR,9R)-9-(4-hydroxy-3,5-dimethoxyphenyl)-8-oxo-5a,6,8a,9-tetrahydro-5H-[2]benzofuro[5,6-f][1,3]benzodioxol-5-yl]amino]-3-[(2-methylpropan-2-yl)oxycarbonylamino]-1-oxopropan-2-yl]carbamate
• CAS: 1443511-08-7
• 化学式: C₃₄H₄₃N₃O₁₂
• 分子量: 685.728
• InChiKey: KGBMDXMTJWQDIQ-LLSXRHJJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  189
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  4β-N-[2'',3''-bis(tert-butoxycarbonylamino)propanoyl]-4'-O-demethyl-podophyllotoxin 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成
  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：

  (5R,5aR,8aS,9S)-9-amino-5-(4-hydroxy-3,5-dimethoxyphenyl)-5,5a,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6(8H)-one 、 N,N'-双(叔丁氧基羰基)-2,3-二氨基丙酸 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 以87%的产率得到4β-N-[2'',3''-bis(tert-butoxycarbonylamino)propanoyl]-4'-O-demethyl-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

文献信息

• Synthesis and anticancer activity of dichloroplatinum(II) complexes of podophyllotoxin
  作者：Xuan Liu、Lin-Lin Zhang、Xiao-Hui Xu、Lin Hui、Jin-Bang Zhang、Shi-Wu Chen

  DOI：10.1016/j.bmcl.2013.04.089

  日期：2013.7

  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.