methyl (2E)-2-[(1R,3S,7S,8E,11S,12S,15S,17R,21R,23S)-12-acetyloxy-11,21-dihydroxy-10,10-dimethyl-19-oxo-17-[(1R)-1-phenylmethoxyethyl]-6,18,27,28,29-pentaoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-13-ylidene]acetate | 304429-13-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: methyl (2E)-2-[(1R,3S,7S,8E,11S,12S,15S,17R,21R,23S)-12-acetyloxy-11,21-dihydroxy-10,10-dimethyl-19-oxo-17-[(1R)-1-phenylmethoxyethyl]-6,18,27,28,29-pentaoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-13-ylidene]acetate
• CAS: 304429-13-8
• 化学式: C₄₀H₅₆O₁₃
• 分子量: 744.877
• InChiKey: PDDMUHFUYZYGKF-AARLTUTGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  53
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  166
• 氢给体数：
  2
• 氢受体数：
  13

反应信息

• 作为反应物：
  描述：

  methyl (2E)-2-[(1R,3S,7S,8E,11S,12S,15S,17R,21R,23S)-12-acetyloxy-11,21-dihydroxy-10,10-dimethyl-19-oxo-17-[(1R)-1-phenylmethoxyethyl]-6,18,27,28,29-pentaoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-13-ylidene]acetate 在 palladium dihydroxide 氢气 作用下， 以 乙酸乙酯 为溶剂， 以93%的产率得到methyl (2E)-2-[(1R,3S,7S,8E,11S,12S,15S,17R,21R,23S)-12-acetyloxy-11,21-dihydroxy-17-[(1R)-1-hydroxyethyl]-10,10-dimethyl-19-oxo-6,18,27,28,29-pentaoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-13-ylidene]acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of bryostatin analogues: the role of the C20 substituent in protein kinase C binding

  摘要：

  The synthesis and biological assay of a new series of designed bryostatin analogues modified at the C20 position are described. These compounds are found to bind to protein kinase C with affinities of up to 1.5 nM, demonstrating that variations at C20 can indeed be used to tune affinity and potentially function. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01100-x
• 作为产物：
  描述：

  [(2S,3S,6S)-3-Acetoxy-6-[(2R,3R)-3-benzyloxy-2-(4-methoxy-phenoxy)-butyl]-2-((E)-4,4-dimethoxy-1,1-dimethyl-but-2-enyl)-2-methoxy-tetrahydro-pyran-(4E)-ylidene]-acetic acid methyl ester 在 amberlyst-15 resin 、 氢氟酸 、 水 、 氟化氢吡啶 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 methyl (2E)-2-[(1R,3S,7S,8E,11S,12S,15S,17R,21R,23S)-12-acetyloxy-11,21-dihydroxy-10,10-dimethyl-19-oxo-17-[(1R)-1-phenylmethoxyethyl]-6,18,27,28,29-pentaoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-13-ylidene]acetate
  参考文献：
  名称：

  Synthesis and biological evaluation of a new class of bryostatin analogues: the role of the C20 substituent in protein kinase C binding

  摘要：

  The synthesis and biological assay of a new series of designed bryostatin analogues modified at the C20 position are described. These compounds are found to bind to protein kinase C with affinities of up to 1.5 nM, demonstrating that variations at C20 can indeed be used to tune affinity and potentially function. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)01100-x

文献信息

• BRYOSTATIN ANALOGUES, SYNTHETIC METHODS AND USES
  申请人：Wender Paul A.

  公开号：US20100280262A1

  公开（公告）日：2010-11-04

  Biologically active compounds related to the bryostatin family of compounds, having simplified spacer domains and/or improved recognition domains are disclosed, including methods of preparing and utilizing the same.