8,8'-Bis-[1,3]dithian-2-yl-6,7,6',7'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,4,1',4'-tetraone | 609848-53-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 8,8'-Bis-[1,3]dithian-2-yl-6,7,6',7'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,4,1',4'-tetraone
• 英文别名: 8-(1,3-dithian-2-yl)-2-[8-(1,3-dithian-2-yl)-6,7-dihydroxy-3-methyl-1,4-dioxo-5-propan-2-ylnaphthalen-2-yl]-6,7-dihydroxy-3-methyl-5-propan-2-ylnaphthalene-1,4-dione
• CAS: 609848-53-5
• 化学式: C₃₆H₃₈O₈S₄
• 分子量: 726.957
• InChiKey: DIEGIYGSKZUDGT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.58
• 重原子数：
  48.0
• 可旋转键数：
  5.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  149.2
• 氢给体数：
  4.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  8,8'-Bis-[1,3]dithian-2-yl-6,7,6',7'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,4,1',4'-tetraone 在 nitrosonium tetrafluoroborate 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 96.0h， 以40%的产率得到棉子酚酛
  参考文献：
  名称：

  New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents

  摘要：

  New dithiane or dithiolane derivatives of gossypol and gossypolone were synthesized with dithiolethane or dithiolpropane in the presence of BF3/Et2O. These thioderivatives exhibited low toxicity on KB cells (human epidermoid carcinoma cells of the mouth). They react easily with electrophiles in aprotic solvents to regenerate gossypolone or to form dehydrogossypoldithianes and dehydrogossypoldithiolanes, which display higher toxicity on KB cells. In addition, the low toxicity of gossypol thioderivatives was reversed by nitric oxide donors in physiological media. These experiments suggest that gossypol and gossypolone dithianes and dithiolanes can be used as prodrugs that target tumor cells surrounded by high concentrations of nitric oxide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00066-x
• 作为产物：
  描述：

  1,3-丙二硫醇 、 棉子酚酛 在 三氟化硼乙醚 作用下， 以 氯仿 为溶剂， 反应 1.0h， 以89%的产率得到8,8'-Bis-[1,3]dithian-2-yl-6,7,6',7'-tetrahydroxy-5,5'-diisopropyl-3,3'-dimethyl-[2,2']binaphthalenyl-1,4,1',4'-tetraone
  参考文献：
  名称：

  New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents

  摘要：

  New dithiane or dithiolane derivatives of gossypol and gossypolone were synthesized with dithiolethane or dithiolpropane in the presence of BF3/Et2O. These thioderivatives exhibited low toxicity on KB cells (human epidermoid carcinoma cells of the mouth). They react easily with electrophiles in aprotic solvents to regenerate gossypolone or to form dehydrogossypoldithianes and dehydrogossypoldithiolanes, which display higher toxicity on KB cells. In addition, the low toxicity of gossypol thioderivatives was reversed by nitric oxide donors in physiological media. These experiments suggest that gossypol and gossypolone dithianes and dithiolanes can be used as prodrugs that target tumor cells surrounded by high concentrations of nitric oxide. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(03)00066-x

文献信息

• 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
• New thioderivatives of gossypol and gossypolone, as prodrugs of cytotoxic agents
  作者：Vi-Thuy Dao、Michael K. Dowd、Christiane Gaspard、Marie-Thérèse Martin、Julie Hémez、Olivier Laprévote、Michel Mayer、Robert J. Michelot

  DOI：10.1016/s0968-0896(03)00066-x

  日期：2003.5

  New dithiane or dithiolane derivatives of gossypol and gossypolone were synthesized with dithiolethane or dithiolpropane in the presence of BF3/Et2O. These thioderivatives exhibited low toxicity on KB cells (human epidermoid carcinoma cells of the mouth). They react easily with electrophiles in aprotic solvents to regenerate gossypolone or to form dehydrogossypoldithianes and dehydrogossypoldithiolanes, which display higher toxicity on KB cells. In addition, the low toxicity of gossypol thioderivatives was reversed by nitric oxide donors in physiological media. These experiments suggest that gossypol and gossypolone dithianes and dithiolanes can be used as prodrugs that target tumor cells surrounded by high concentrations of nitric oxide. (C) 2003 Elsevier Science Ltd. All rights reserved.