4-β-(2''-chloroacetamido)podophyllotoxin | 748151-22-6

• 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: 4-β-(2''-chloroacetamido)podophyllotoxin
• 英文别名: N-[(5S,5aS,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-chloroacetamide
• CAS: 748151-22-6
• 化学式: C₂₄H₂₄ClNO₈
• 分子量: 489.909
• InChiKey: WZDBPQCRVZJXEN-ITGOXPRASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  34
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  102
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-β-(2''-chloroacetamido)podophyllotoxin 在 溶剂黄146 、 硫脲 作用下， 反应 4.0h， 以82%的产率得到4β-amino-4-deoxypodophyllotoxin
  参考文献：
  名称：

  A novel, stereoselective and practical protocol for the synthesis of 4β-aminopodophyllotoxins

  摘要：

  摘要：使用氯乙腈与侧耳草毒素进行里特反应，然后在产生的氯乙酰胺中使用硫脲进行氯乙酰基的裂解，经典加热和超声波条件下均可有效地合成4β-氨基侧耳草毒素。一般来说，相对于经典加热反应，超声波反应的反应速率和收率都有显着的提高。

  DOI：

  10.2478/s11696-010-0020-z
• 作为产物：
  描述：

  氯乙腈 、 鬼臼毒素 在 alumina methanesulfonic acid 作用下， 反应 2.0h， 以80%的产率得到4-β-(2''-chloroacetamido)podophyllotoxin
  参考文献：
  名称：

  A novel, stereoselective and practical protocol for the synthesis of 4β-aminopodophyllotoxins

  摘要：

  摘要：使用氯乙腈对鬼臼毒素进行里特反应，并在所得的氯乙酰胺中使用硫脲裂解氯乙酰基团，经典加热和超声波条件下均可高效合成4β-氨基鬼臼毒素。一般来说，相对于经典加热反应，超声波反应的反应速率和收率都有显著的提高。

  DOI：

  10.2478/s11696-010-0020-z

文献信息

• Podophyllotoxin derivatives as antitumor agents
  申请人：Kamal Ahmed

  公开号：US20070066837A1

  公开（公告）日：2007-03-22

  This invention relates to podophyllotoxin derivatives, more particularly to 4β-amino and 4β-amido derivatives of podophyllotoxin and 4′-O-demethylepipodophyllotoxin, which are useful for the treatment of tumors. Processes for the preparation of the compounds disclosed herein, pharmaceutical compositions containing these compounds, and methods for treating tumors are provided. The invention further relates to stereoselective compounds of podophyllotoxin and 4′-O-demethylepipodophyllotoxin derivatives.

  本发明涉及足叶草毒素衍生物，更具体地涉及4β-氨基和4β-酰胺衍生物以及4'-O-去甲基表儿茶素，这些衍生物对肿瘤的治疗有用。本发明提供了制备所述化合物的方法，含有这些化合物的制药组合物以及治疗肿瘤的方法。本发明还涉及足叶草毒素和4'-O-去甲基表儿茶素衍生物的立体选择性化合物。
• Design, synthesis and potent cytotoxic activity of novel podophyllotoxin derivatives
  作者：Wen-Qun Li、Xu-Li Wang、Keduo Qian、Ying-Qian Liu、Chih-Ya Wang、Liu Yang、Jin Tian、Susan L. Morris-Natschke、Xing-Wen Zhou、Kuo-Hsiung Lee

  DOI：10.1016/j.bmc.2013.01.069

  日期：2013.4

  Twenty new acyl thiourea derivatives of podophyllotoxin and 4'-demethylepipodophyllotoxin were prepared and screened for their cytotoxicity against four human tumor cell lines, A-549, DU-145, KB, and KBvin. With IC50 values of 0.098-1.13 mu M, compounds 13b, 13c, and 13o displayed much better cytotoxic activity than the control etoposide. Most importantly, 13b and 13o exhibited promising cytotoxicity against the drug resistant tumor cell line KBvin with IC50 values of 0.098 and 0.13 mu M, respectively, while etoposide lost activity completely. Structure-activity relationship (SAR) correlations of the new derivatives have been established. Compounds 13b and 13o merit further development as a new generation of epipodophyllotoxin-derived antitumor clinical trial candidates. (C) 2013 Elsevier Ltd. All rights reserved.
• A novel, stereoselective and practical protocol for the synthesis of 4β-aminopodophyllotoxins
  作者：Ying-Qian Liu、Lin-Hai Li、Liu Yang、Hong-Yu Li

  DOI：10.2478/s11696-010-0020-z

  日期：2010.1.1

  Ritter reaction of podophyllotoxins with chloroacetonitrile and subsequent cleavage of the chloroacetyl group in the resulting chloroacetamide with thiourea under both classical heating and ultrasonic conditions is an efficient procedure for the synthesis of 4β-aminopodophyllotoxins. In general, significant improvements in the rates of reaction and yields of the sonochemical reactions relative to the classical heating reactions were observed.

  摘要：使用氯乙腈对鬼臼毒素进行里特反应，并在所得的氯乙酰胺中使用硫脲裂解氯乙酰基团，经典加热和超声波条件下均可高效合成4β-氨基鬼臼毒素。一般来说，相对于经典加热反应，超声波反应的反应速率和收率都有显著的提高。