schweinfurthin A | 217476-92-1

• 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 A
• 英文别名: (2S,3R,4aR,9aR)-7-[(E)-2-[4-[(2E)-3,7-dimethylocta-2,6-dienyl]-3,5-dihydroxyphenyl]ethenyl]-1,1,4a-trimethyl-3,4,9,9a-tetrahydro-2H-xanthene-2,3,5-triol
• CAS: 217476-92-1
• 化学式: C₃₄H₄₄O₆
• 分子量: 548.72
• InChiKey: HSDZWMOBUPRZEU-LXYWBZBZSA-N

物化性质

• 沸点：
  732.4±60.0 °C(Predicted)
• 密度：
  1.201±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  110
• 氢给体数：
  5
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  [3-Bromo-4-(phenylmethoxymethoxy)phenyl]methanol 在 manganese(IV) oxide 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 正丁基锂 、 四丙基高钌酸铵 、 四甲基乙二胺 、 cerium(III) chloride heptahydrate 、 三氟化硼乙醚 、 水 、 sodium hydride 、 对甲苯磺酸 、 N-甲基吗啉氧化物 、 二异丙胺 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 potassium hydroxide 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 hexanes 、 乙醚 、 乙醇 、 二氯甲烷 、 水 、 mineral oil 、 叔丁醇 为溶剂， -78.0~20.0 ℃ 、101.33 kPa 条件下， 反应 209.88h， 生成 schweinfurthin A
  参考文献：
  名称：

  Exploration of Cascade Cyclizations Terminated by Tandem Aromatic Substitution: Total Synthesis of (+)-Schweinfurthin A

  摘要：

  The termination of epoxide-initiated cascade cyclizations with a range of "protected" phenols is described. When the protecting group can be lost as a stabilized electrophile, the cascade process continues beyond ring closure to afford products which have undergone a tandem electrophilic aromatic substitution. A number of groups have proven viable in this process and the regiochemistry of their substitution reactions has been studied. Application of this methodology in the first total synthesis of (+)-schweinfurthin A, a potent antiproliferative agent, has been achieved.

  DOI：

  10.1021/jo1022102

文献信息

• 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：University of Iowa Research Foundation

  公开号：EP2310380B1

  公开（公告）日：2013-04-17
• 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.
• METHODS AND MATERIALS FOR TREATING CANCER
  申请人：The Penn State Research Foundation

  公开号：US20200405688A1

  公开（公告）日：2020-12-31

  This document provides methods and materials for treating cancer. For example, methods and materials for using one or more schweinfurthin compounds and one or more immune-checkpoint inhibitors to treat a mammal having cancer are provided.

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