2-(3-hexen-1,5-diynyl)benzonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-hexen-1,5-diynyl)benzonitrile
• 英文别名: 2-(3-hexen-1,5-diyne)benzonitrile；2-[(Z)-hex-3-en-1,5-diynyl]benzonitrile
• 化学式: C₁₃H₇N
• 分子量: 177.205
• InChiKey: ZZLUAXYMBKYWII-ARJAWSKDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  23.8
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-(3-hexen-1,5-diynyl)benzonitrile 、 2-碘吡啶 在 四(三苯基膦)钯 copper(l) iodide 、 正丁胺 作用下， 以 乙醚 为溶剂， 反应 6.0h， 以50%的产率得到2-(6-(2-pyridinyl)-3-hexen-1,5-diynyl)benzonitrile
  参考文献：
  名称：

  Remarkable G2/M phase arrest and apoptotic effect performed by 2-(6-aryl-3-hexen-1,5-diynyl) benzonitrile antitumor agents

  摘要：

  2-(6-aryl-3-hexen-1,5-diynyl)benzonitriles 3a-j showed growth inhibition effects on a full panel of 60 human cancer cell lines in low micro-concentrations, in which compounds 3c,d displayed a significant G2/M arrest in the cell growth cycle compared with other derivatives and an apoptotic progress induction were also shown by 3a-d. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.014
• 作为产物：
  描述：

  2-乙炔基苯甲腈 在 四(三苯基膦)钯 copper(l) iodide 、 四丁基氟化铵 、 正丁胺 作用下， 以 四氢呋喃 、 乙醚 为溶剂， 反应 6.0h， 生成 2-(3-hexen-1,5-diynyl)benzonitrile
  参考文献：
  名称：

  Remarkable G2/M phase arrest and apoptotic effect performed by 2-(6-aryl-3-hexen-1,5-diynyl) benzonitrile antitumor agents

  摘要：

  2-(6-aryl-3-hexen-1,5-diynyl)benzonitriles 3a-j showed growth inhibition effects on a full panel of 60 human cancer cell lines in low micro-concentrations, in which compounds 3c,d displayed a significant G2/M arrest in the cell growth cycle compared with other derivatives and an apoptotic progress induction were also shown by 3a-d. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2003.12.014

文献信息

• Pharmaceutical compositions comprising aryl-substituted acyclic enediyne compounds
  申请人：Wu Ming-Jung

  公开号：US20050004211A1

  公开（公告）日：2005-01-06

  A pharmaceutical compositions comprises a compound of formula (I): or a pharmaceutically acceptable salt thereof: wherein R 1 ═R 2 ═H; or R 1 and R 2 together form a moiety represented by the formula R 3 represents a substituted or unsubstituted alkyl having 4-30 carbon atoms, or a substituted or unsubstituted aryl group having 3-30 carbon atoms; and R 4 represents a substituted or unsubstituted aryl group having 3-30 carbon atoms; with the proviso that R 3 is not butyl, pentyl, tetrahydropyranyloxymethyl, tetrahydropyranyloxypropyl or phenyl when R 1 ═R 2 ═H and R 4 is o-cyanophenyl,; and with the proviso that R 3 is not butyl when R 1 ═R 2 ═H and R 4 is phenyl. The pharmaceutical composition may be used to treat a subject afflicted with a tumor/cancer by inhibiting topoisomerase I activities or blocking the S phase or G 2 /M phase of the tumor/cancer cells.

  一种药物组合物包括化合物的结构式(I)：或其药用可接受的盐：其中R1=R2=H；或R1和R2一起形成由结构式表示的基团R3代表具有4-30个碳原子的取代或未取代的烷基，或具有3-30个碳原子的取代或未取代的芳基；和R4代表具有3-30个碳原子的取代或未取代的芳基；但R3不是丁基、戊基、四氢吡喃氧甲基、四氢吡喃氧丙基或苯基，当R1=R2=H和R4是邻氰基苯基时；且R3不是丁基，当R1=R2=H和R4是苯基时。该药物组合物可用于通过抑制拓扑异构酶I活性或阻断肿瘤/癌细胞的S期或G2/M期治疗患有肿瘤/癌症的受试者。
• US7332623B2
  申请人：——

  公开号：US7332623B2

  公开（公告）日：2008-02-19