9,12-Diazapentacyclo[11.6.1.02,10.03,8.016,20]icosa-1(19),2(10),3,5,7,16(20),17-heptaen-11-one | 1311994-08-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: 9,12-Diazapentacyclo[11.6.1.02,10.03,8.016,20]icosa-1(19),2(10),3,5,7,16(20),17-heptaen-11-one
• CAS: 1311994-08-7
• 化学式: C₁₈H₁₄N₂O
• 分子量: 274.322
• InChiKey: IOUUFOJANCGJSV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  7-溴-1-茚满酮 在 2-双环己基膦-2',6'-二甲氧基联苯 、 titanium(IV) isopropylate 、 1,1'-双(二苯基膦)二茂铁 、 sodium tetrahydroborate 、 乙醇 、 氨 、 palladium diacetate 、 sodium 、 三乙胺 、 cesium fluoride 、 三氟乙酸 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 乙醇 、 二氯甲烷 为溶剂， 反应 71.33h， 生成 9,12-Diazapentacyclo[11.6.1.02,10.03,8.016,20]icosa-1(19),2(10),3,5,7,16(20),17-heptaen-11-one
  参考文献：
  名称：

  Rigid Analogues of Antimitotic Indolobenzazepinones: New Insights into Tubulin Binding via Molecular Modeling

  摘要：

  Two rigid analogues of 5-ethylindolobenzazepinone 4, a potent c-ytotoxic agent and inhibitor of tubulin polymerization, were prepared. The first was the indane derivative 5, in which the ethyl group is attached to the benzo moiety. The second was the pyrrolidine analogue 6, in which the ethyl chain was bound to the lactam nitrogen. While both compounds were considerably less active inhibitors of KB cell growth as compared to 4, inhibition of tubulin polymerization was only moderately reduced. Tubulin docking studies indicated that the aR and aS atropoisomers of 5 and 6 occupy different binding pockets at the colchicine binding site. Conversely, both aS-5 and aS-6 occupy the same binding pocket as aSS-4 but do not benefit from the favorable hydrophobic interactions provided by the CS alkyl group of 4, thus possibly explaining their lower activities.

  DOI：

  10.1021/ml200024y