[(1S,3S,7S,8E,11S,12S,13E,15S,17R,21R,23R)-11,21-dihydroxy-17-(hydroxymethyl)-13-(2-methoxy-2-oxoethylidene)-10,10-dimethyl-19,25-dioxo-6,18,27,28,29-pentaoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate | 1041849-45-9

• 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: [(1S,3S,7S,8E,11S,12S,13E,15S,17R,21R,23R)-11,21-dihydroxy-17-(hydroxymethyl)-13-(2-methoxy-2-oxoethylidene)-10,10-dimethyl-19,25-dioxo-6,18,27,28,29-pentaoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate
• CAS: 1041849-45-9
• 化学式: C₃₈H₅₈O₁₄
• 分子量: 738.87
• InChiKey: MZJWHSNTFZRLAG-RPEIDPBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  52
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  194
• 氢给体数：
  3
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  、 Octanoic acid (2S,3S,6S)-6-[(R)-3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-2-((E)-1,1-dimethyl-4-oxo-but-2-enyl)-2-hydroxy-4-[1-methoxycarbonyl-meth-(E)-ylidene]-tetrahydro-pyran-3-yl ester 在 2,6-二甲基吡啶 、 叔丁基二甲硅基三氟甲磺酸酯 、 水 、 potassium carbonate 作用下， 以 二氯甲烷 、 甲醇 为溶剂， 反应 22.5h， 以38%的产率得到[(1S,3S,7S,8E,11S,12S,13E,15S,17R,21R,23R)-11,21-dihydroxy-17-(hydroxymethyl)-13-(2-methoxy-2-oxoethylidene)-10,10-dimethyl-19,25-dioxo-6,18,27,28,29-pentaoxatetracyclo[21.3.1.13,7.111,15]nonacos-8-en-12-yl] octanoate
  参考文献：
  名称：

  The Design, Synthesis, and Evaluation of C7 Diversified Bryostatin Analogs Reveals a Hot Spot for PKC Affinity

  摘要：

  The first series of systematically varied C7-functionalized bryostatin analogs (12 members in all) have been synthesized through an efficient and convergent route. A new hotspot for PKC affinity, not present in the natural products, has been discovered, allowing for affinity control and potentially for selective regulation of PKC isozymes. Several analogs exhibit single-digit nanomolar affinity to PKC and display superior activity compared to bryostatin against the leukemia cell line K562.

  DOI：

  10.1021/ol801235h

文献信息

• The Design, Synthesis, and Evaluation of C7 Diversified Bryostatin Analogs Reveals a Hot Spot for PKC Affinity
  作者：Paul A. Wender、Vishal A. Verma

  DOI：10.1021/ol801235h

  日期：2008.8.7

  The first series of systematically varied C7-functionalized bryostatin analogs (12 members in all) have been synthesized through an efficient and convergent route. A new hotspot for PKC affinity, not present in the natural products, has been discovered, allowing for affinity control and potentially for selective regulation of PKC isozymes. Several analogs exhibit single-digit nanomolar affinity to PKC and display superior activity compared to bryostatin against the leukemia cell line K562.