13,18-Dibromo-2-oxapentacyclo[22.2.2.13,7.010,15.016,21]nonacosa-1(26),3,5,7(29),10,12,14,16(21),17,19,24,27-dodecaene-4,12,17-triol | 1366642-15-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: 13,18-Dibromo-2-oxapentacyclo[22.2.2.13,7.010,15.016,21]nonacosa-1(26),3,5,7(29),10,12,14,16(21),17,19,24,27-dodecaene-4,12,17-triol
• CAS: 1366642-15-0
• 化学式: C₂₈H₂₂Br₂O₄
• 分子量: 582.288
• InChiKey: LHGLJKZCTATRNZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  34
• 可旋转键数：
  0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  (2-甲酰基-6-甲氧基苯基)三氟甲磺酸酯 在 盐酸 、 N-溴代丁二酰亚胺(NBS) 、 四(三苯基膦)钯 、 18-冠醚-6 、 5%-palladium/activated carbon 、 水 、 氢气 、 三溴化硼 、 四氯化钛 、 sodium carbonate 、 potassium carbonate 、 三乙胺 、 锌 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 、 乙腈 为溶剂， -40.0~20.0 ℃ 、300.01 kPa 条件下， 反应 142.0h， 生成 18-Bromo-2-oxapentacyclo[22.2.2.13,7.010,15.016,21]nonacosa-1(26),3,5,7(29),10(15),11,13,16(21),17,19,24,27-dodecaene-4,12,17-triol 、 13,18-Dibromo-2-oxapentacyclo[22.2.2.13,7.010,15.016,21]nonacosa-1(26),3,5,7(29),10,12,14,16(21),17,19,24,27-dodecaene-4,12,17-triol
  参考文献：
  名称：

  Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents

  摘要：

  Based on the core skeleton of the total synthesized bisbibenzyl marchantin C, riccardin D and plagiochin E, a series of brominated and aminomethylated derivatives of above three bisbibenzyls have been synthesized and their cytotoxic activity against KB, MCF-7 and PC3 cell lines has been preliminary evaluated. The bio-test results revealed that the brominated derivatives 21, 22, 24, 25 and 28 exhibited excellent antiproliferative activity, with IC50 value lower than their parent compounds. As a most potent microtubule depolymerization agent, compound 28 was found to arrest cells at the G(2)/M phase of the cell cycle as determined by the flow cytometry assay in PC3 cell line. The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.004

文献信息

• Synthesis of macrocyclic bisbibenzyl derivatives and their anticancer effects as anti-tubulin agents
  作者：Juan Jiang、Bin Sun、Yan-yan Wang、Min Cui、Li Zhang、Chang-zhi Cui、Yan-feng Wang、Xi-gong Liu、Hong-xiang Lou

  DOI：10.1016/j.bmc.2012.02.004

  日期：2012.4

  Based on the core skeleton of the total synthesized bisbibenzyl marchantin C, riccardin D and plagiochin E, a series of brominated and aminomethylated derivatives of above three bisbibenzyls have been synthesized and their cytotoxic activity against KB, MCF-7 and PC3 cell lines has been preliminary evaluated. The bio-test results revealed that the brominated derivatives 21, 22, 24, 25 and 28 exhibited excellent antiproliferative activity, with IC50 value lower than their parent compounds. As a most potent microtubule depolymerization agent, compound 28 was found to arrest cells at the G(2)/M phase of the cell cycle as determined by the flow cytometry assay in PC3 cell line. The remarkable biological profile and novel structure of these bisbibenzyl derivatives make them possible as promising candidates for clinical development as chemotherapeutic agents. (C) 2012 Elsevier Ltd. All rights reserved.