schweinfurthin B | 217476-93-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: schweinfurthin B
• 英文别名: (2S,3R,4aR,9aR)-7-[(E)-2-[4-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5-dihydroxyphenyl]ethenyl]-5-methoxy-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,3-diol
• CAS: 217476-93-2
• 化学式: C₃₅H₄₆O₆
• 分子量: 562.747
• InChiKey: UPTXDGJFJGCFDE-NASSATPLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  41
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.49
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (2S,3R,4aR,9aR)-7-[(E)-2-[4-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5-bis(methoxymethoxy)phenyl]ethenyl]-5-methoxy-2-(methoxymethoxy)-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthen-3-ol 在 对甲苯磺酸 作用下， 以 甲醇 为溶剂， 反应 46.0h， 以55%的产率得到schweinfurthin B
  参考文献：
  名称：

  （+）-Schweinfurthins B和E的全合成

  摘要：

  已经完成了（+）-schweinfurthin B（一种有效且具有差异活性的细胞毒剂）的第一个全合成。从市售的香兰素完成最长的线性序列仅需完成16个步骤即可完成合成。关键的合成转化包括Shi环氧化和通过用BF 3 ·OEt 2处理所得的环氧化物引发的有效级联环化。此外，使用甲醚作为苄醇的稳定保护基团可以显着提高整个序列的效率。苄基醚可以通过用DDQ氧化从富电子芳族体系中除去，从而以定量收率提供所需的醛中间体，并缩短了合成顺序。然后通过所需的顺式立体化学引入A-环二醇成为可能，这是通过与苯甲醛进行醛醇缩合缩合以在C-3位置引入作为潜在羰基的烯烃而突出的短序列。这种合成首次建立了天然产物的绝对立体化学，并提供了可促进生物学研究的规模的材料。

  DOI：

  10.1021/jo901161m

文献信息

• [EN] SCHWEINFURTHIN ANALOGUES<br/>[FR] ANALOGUES DE LA SCHWEINFURTHINE
  申请人：UNIV IOWA RES FOUND

  公开号：WO2009158516A1

  公开（公告）日：2009-12-30

  The invention provides fluorescent schweinfurthin analogs of formula(I) which are useful as probes and for the treatment of cancer and other diseases.

  该发明提供了公式(I)的荧光施文富尔汀类似物，可用作探针，用于治疗癌症和其他疾病。
• OSW-1 ANALOGS AND CONJUGATES, AND USES THEREOF
  申请人：Shair Matthew D.

  公开号：US20140135279A1

  公开（公告）日：2014-05-15

  Provided are a number of compounds structurally related to OSW-1, a natural compound that binds OSBPs. Also provided are pharmaceutical compositions comprising the OSW-1 analogs, as well as methods for use of these OSW-1 analogs, or pharmaceutically acceptable salts, enantiomers, or stereoisomers thereof in the treatment of atherosclerosis. Alzheimer's disease, and cancer, including p21-deficient cancer. Conjugates of OSW-1 analogs with monoclonal antibodies, including monoclonal antibodies targeted to cancer cells, are also provided. Also provided are pharmaceutical compositions comprising the conjugates, as well as methods for use of these conjugates, in the treatment of cancer, including p21-deficient cancer.

  提供了一些结构与OSW-1相似的化合物，OSW-1是一种与OSBPs结合的天然化合物。还提供了包含OSW-1类似物的制药组合物，以及使用这些OSW-1类似物或其药学上可接受的盐、对映体或立体异构体治疗动脉粥样硬化、阿尔茨海默病和癌症，包括p21缺陷癌症的方法。还提供了与单克隆抗体结合的OSW-1类似物共轭物，包括针对癌细胞的单克隆抗体。还提供了包含这些共轭物的制药组合物，以及使用这些共轭物治疗癌症，包括p21缺陷癌症的方法。
• SCHWEINFURTHIN ANALOGUES
  申请人：Wiemer David F.

  公开号：US20080227852A1

  公开（公告）日：2008-09-18

  Methods and intermediates for preparing enantiomerically enriched Schweinfurthin analogs which are useful for the treatment of cancer, as well as novel Schweinfurthin analogs having anti-cancer activity, compositions comprising such analogs and therapeutic methods comprising administering such analogs.

  本发明涉及用于治疗癌症的对映富集的Schweinfurthin类似物的制备方法和中间体，以及具有抗癌活性的新型Schweinfurthin类似物、包含这种类似物的组合物和包括给予这种类似物的治疗方法。
• SCHWEINFURTHINS AND USES THEREOF
  申请人：The U.S.A. as represented by the Secretary, Department of Health and Human Services

  公开号：EP2432466B1

  公开（公告）日：2018-03-28
• Compounds That Bind Oxysterol Binding Proteins, and Methods of Use Thereof
  申请人：Shair Matthew D.

  公开号：US20110319352A1

  公开（公告）日：2011-12-29

  The invention relates in part to the discovery that certain CRAMs, such as schweinfurthin A, target OSBPs (a family of oxysterol binding proteins). Because OSBPs have been shown to be integral to atherosclerosis and Alzheimer's disease (AD), one aspect of the invention relates to the use of CRAMs, or a pharmaceutically acceptable salt, biologically active metabolite, solvate, hydrate, prodrug, enantiomer or stereoisomer thereof, in the treatment and/or prevention of atherosclerosis, Alzheimer's disease and related disorders. Another aspect of the invention relates to novel derivatives of CRAMs, or a pharmaceutically acceptable salt, biologically active metabolite, solvate, hydrate, prodrug, enantiomer or stereoisomer thereof, for the treatment and/or prevention of atherosclerosis, Alzheimer's disease and related disorders. Another aspect of the invention relates to the use of an immobilized CRAMs, such as OSW-I, to aid in screening of compounds to identify additional OSBP binders. Other aspects of the invention relate to the use of CRAMs to treat cancer, such as p21-deficient cancers.

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