| 1431705-85-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• CAS: 1431705-85-9
• 化学式: C₄₁H₅₁NO₈
• 分子量: 685.858
• InChiKey: ANEOPWBNBLWZMR-FXQOQPJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.48
• 重原子数：
  50.0
• 可旋转键数：
  12.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.51
• 拓扑面积：
  115.54
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  在 palladium on activated charcoal 、 氢气 、 三乙胺 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 8.0h， 生成 N-[4-hydroxy-2-[4-[(1S,3R,5R,9R,13R)-9-(hydroxymethyl)-16,16-dimethyl-7,11-dioxo-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecan-3-yl]butyl]phenyl]acetamide
  参考文献：
  名称：

  Structure–activity studies on the side chain of a simplified analog of aplysiatoxin (aplog-1) with anti-proliferative activity

  摘要：

  We have recently developed a simplified analog of aplysiatoxin (aplog-1) as an activator of protein kinase C (PKC) with anti-proliferative activity like bryostain 1. To identify sites in aplog-1 that could be readily modified to optimize therapeutic performance and to develop a molecular probe for examining the analog's mode of action, substituent effects on the phenol ring were systematically examined. Whereas hydrophilic acetamido derivatives were less active than aplog-1 in inhibiting cancer cell growth and binding to PKCS, introduction of hydrophobic bromine and iodine atoms enhanced both biological activities. The anti-proliferative activity was found to correlate closely with molecular hydrophobicity, and maximal activity was observed at a log P value of 4.0-4.5. On the other hand, an induction test with Epstein-Barr virus early antigen demonstrated that these derivatives have less tumor-promoting activity in vitro than aplog-1 regardless of the hydrophobicity of their substituents. These results would facilitate rapid preparation of molecular probes to examine the mechanism of the unique biological activities of aplog-1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.013
• 作为产物：
  描述：

  (1S,3R,5R,9R,13R)-16,16-dimethyl-9-(phenylmethoxymethyl)-3-[4-(3-phenylmethoxyphenyl)butyl]-2,6,10,17-tetraoxatricyclo[11.3.1.11,5]octadecane-7,11-dione 在 sodium tetrahydroborate 、 18-冠醚-6 、 nickel(II) chloride hexahydrate 、 四丁基硝酸铵 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  Structure–activity studies on the side chain of a simplified analog of aplysiatoxin (aplog-1) with anti-proliferative activity

  摘要：

  We have recently developed a simplified analog of aplysiatoxin (aplog-1) as an activator of protein kinase C (PKC) with anti-proliferative activity like bryostain 1. To identify sites in aplog-1 that could be readily modified to optimize therapeutic performance and to develop a molecular probe for examining the analog's mode of action, substituent effects on the phenol ring were systematically examined. Whereas hydrophilic acetamido derivatives were less active than aplog-1 in inhibiting cancer cell growth and binding to PKCS, introduction of hydrophobic bromine and iodine atoms enhanced both biological activities. The anti-proliferative activity was found to correlate closely with molecular hydrophobicity, and maximal activity was observed at a log P value of 4.0-4.5. On the other hand, an induction test with Epstein-Barr virus early antigen demonstrated that these derivatives have less tumor-promoting activity in vitro than aplog-1 regardless of the hydrophobicity of their substituents. These results would facilitate rapid preparation of molecular probes to examine the mechanism of the unique biological activities of aplog-1. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.03.013