gossypol bis(anhydro oxime)tetraacatate | 103068-43-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: gossypol bis(anhydro oxime)tetraacatate
• 英文别名: [7-Acetyloxy-12-(6,7-diacetyloxy-11-methyl-8-propan-2-yl-2-oxa-3-azatricyclo[7.3.1.05,13]trideca-1(12),3,5,7,9(13),10-hexaen-12-yl)-11-methyl-8-propan-2-yl-2-oxa-3-azatricyclo[7.3.1.05,13]trideca-1(12),3,5,7,9(13),10-hexaen-6-yl] acetate
• CAS: 103068-43-5
• 化学式: C₃₈H₃₆N₂O₁₀
• 分子量: 680.711
• InChiKey: SUVHSROODDFYMO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7
• 重原子数：
  50
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  gossypol bis(anhydro oxime)tetraacatate 在 水 、 乙酸酐 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 8,8'-二氰基-6,6',7,7'-四羟基-3,3'-二甲基-5,5'-二(丙烷-2-基)-2,2'-联萘-1,1'-二基二乙酸酯
  参考文献：
  名称：

  Biologically active derivatives of gossypol: synthesis and antimalarial activities of peri-acylated gossylic nitriles

  摘要：

  A series of peri-acylated gossylic nitriles were synthesized from gossypol dioxime by treatment of the dioxime with the appropriate acid anhydride and its salt. The reaction pathway was elucidated by isolation and characterization of intermediates. Peri-acylated gossylic nitriles (acyl = acetyl, propionyl, butyryl, and valeryl) were compared with gossypol for activity against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. The gossylic nitriles all retain activity, with activity increasing with the length of the peri-acyl group. Gossylic nitrile 1,1'-divalerate shows antimalarial activity comparable to gossypol itself. The peri-acylated gossylic nitriles are strong inhibitors of parasite lactate dehydrogenase.

  DOI：

  10.1021/jm00159a043
• 作为产物：
  描述：

  gossypol dioxime 在 乙酸酐 作用下， 反应 8.0h， 生成 gossypol bis(anhydro oxime)tetraacatate
  参考文献：
  名称：

  Biologically active derivatives of gossypol: synthesis and antimalarial activities of peri-acylated gossylic nitriles

  摘要：

  A series of peri-acylated gossylic nitriles were synthesized from gossypol dioxime by treatment of the dioxime with the appropriate acid anhydride and its salt. The reaction pathway was elucidated by isolation and characterization of intermediates. Peri-acylated gossylic nitriles (acyl = acetyl, propionyl, butyryl, and valeryl) were compared with gossypol for activity against both chloroquine-sensitive and chloroquine-resistant strains of Plasmodium falciparum. The gossylic nitriles all retain activity, with activity increasing with the length of the peri-acyl group. Gossylic nitrile 1,1'-divalerate shows antimalarial activity comparable to gossypol itself. The peri-acylated gossylic nitriles are strong inhibitors of parasite lactate dehydrogenase.

  DOI：

  10.1021/jm00159a043

文献信息

• JAGT, DAVID L. JANDER;ROYER, ROBERT E.
  作者：JAGT, DAVID L. JANDER、ROYER, ROBERT E.

  DOI：——

  日期：——
• SMALL MOLECULE ANTAGONISTS OF BCL-2 FAMILY PROTEINS
  申请人：Wang Shaomeng

  公开号：US20090082424A1

  公开（公告）日：2009-03-26

  The present invention relates to naturally occurring and chemically synthesized small molecule antagonists of Bcl-2 family proteins. In particular, the present invention provides gossypol compounds (e.g., isomers, enantiomers, racemic compounds, metabolites, derivatives, pharmaceutically acceptable salts, in combination with acids or bases, and the like) and methods of using these compounds as antagonists of the anti-apoptotic effects of Bcl-2 family member proteins (e.g., Bcl-2, Bcl-X L , and the like). The present invention also provides compositions comprising gossypol compounds and optionally one or more additional therapeutic agents (e.g., anticancer/chemotherapeutic agents). The present invention also provides methods for treating diseases and pathologies (e.g., neoplastic diseases) comprising administering a composition comprising gossypol compounds and optionally one or more additional therapeutic agents (e.g., anticancer/chemotherapeutic agents) and/or techniques (e.g., radiation therapies, surgical interventions, and the like) to a subject or in vitro cells, tissues, and organs.
• SMALL MOLECULE ANTAGONISTS OF BCL2 FAMILY PROTEINS
  申请人：Wang Shaomeng

  公开号：US20100069344A1

  公开（公告）日：2010-03-18

  The present invention relates to naturally occurring and chemically synthesized small molecule antagonists of Bcl-2 family proteins. In particular, the present invention provides gossypol compounds (e.g., isomers, enantiomers, racemic compounds, metabolites, derivatives, pharmaceutically acceptable salts, in combination with acids or bases, and the like) and methods of using these compounds as antagonists of the anti-apoptotic effects of Bcl-2 family member proteins (e.g., Bcl-2, Bcl-X L, and the like). The present invention also provides compositions comprising gossypol compounds and optionally one or more additional therapeutic agents (e.g., anticancer/chemotherapeutic agents). The present invention also provides methods for treating diseases and pathologies (e.g., neoplastic diseases) comprising administering a composition comprising gossypol compounds and optionally one or more additional therapeutic agents (e.g., anticancer/chemotherapeutic agents) and/or techniques (e.g., radiation therapies, surgical interventions, and the like) to a subject or in vitro cells, tissues, and organs.
• US7432304B2
  申请人：——

  公开号：US7432304B2

  公开（公告）日：2008-10-07
• US8163805B2
  申请人：——

  公开号：US8163805B2

  公开（公告）日：2012-04-24