2-(7-(2-tetrahydropyranyloxy)-3(Z)-hepten-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-(7-(2-tetrahydropyranyloxy)-3(Z)-hepten-1,5-diynyl)benzonitrile
• 英文别名: 2-(7-(tetrahydropyranyloxy)-3-(Z)-hepten-1,5-diynyl)-benzonitrile；2-[(Z)-7-(oxan-2-yloxy)hept-3-en-1,5-diynyl]benzonitrile
• 化学式: C₁₉H₁₇NO₂
• 分子量: 291.349
• InChiKey: FHNFIYJZXHGKDR-UPHRSURJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(7-(2-tetrahydropyranyloxy)-3(Z)-hepten-1,5-diynyl)benzonitrile 在 sodium methylate 、 二甲基亚砜 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以21%的产率得到1-(Tetrahydro-pyran-2-yloxymethyl)-5H-phenanthridin-6-one
  参考文献：
  名称：

  Anionic Cycloaromatization of 1-Aryl-3-hexen-1,5-diynes Initiated by Methoxide Addition:  Synthesis of Phenanthridinones, Benzo[c]phenanthridinones, and Biaryls

  摘要：

  Treatment of 2-((Z)-6-substituted-3-hexene-1,5-diynyl)benzonitriles with sodium methoxide in refluxing methanol in the presence of a polar aprotic solvent, such as DMSO, HMPA, THF, or 18-crown-6, gave phenanthridinones in 21-77% yields. In these cases, addition of 10% DMSO into the reaction mixture gave the highest yield. On the other hand, methanolysis of 2-(2-(2-dalkynylphenyl)ethynyl)benzonitriles under the same reaction conditions gave benzo[c]phenanthridinones in 31-57% yields. Methanolysis of (Z)-1-aryl-3-hexen-1,5-diynes in the presence of 2 equiv of tetrabutylammonium iodide gave biaryls in 14-64% yields. It is found that the reactions with aryl groups bearing electron-withdrawing groups proceeded at greater rates and gave better yields.

  DOI：

  10.1021/jo010693h
• 作为产物：
  描述：

  2-乙炔基苯甲腈 、 (Z)-1-choro-5-<(2-tetrahydropyranyl)oxy>-1-penten-3-yne 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， 生成 2-(7-(2-tetrahydropyranyloxy)-3(Z)-hepten-1,5-diynyl)benzonitrile
  参考文献：
  名称：

  Pharmaceutical compositions comprising aryl-substituted acyclic enediyne compounds

  摘要：

  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。

  公开号：

  US20050004211A1

文献信息

• Aryl-substituted acyclic enediyne compounds
  申请人：Wu Ming-Jung

  公开号：US20050004212A1

  公开（公告）日：2005-01-06

  This invention provides aryl-substituted acyclic enediyne compounds of formula (I): or a pharmaceutically acceptable salt or solvate 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 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 compounds of formula (I) are found to have inhibitory activities against topoisomerase I or act as a S phase or G2/M phase blocker.

  本发明提供了式（I）的芳基取代的无环炔二烯化合物或其药学上可接受的盐或溶剂，其中R1═R2═H；或R1和R2结合形成由式表示的基团R3，其中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基团；而R代表具有3-30个碳原子的取代或未取代的芳基基团；但是当R1═R2═H且R4为o-氰基苯基时，R3不是丁基，戊基，四氢吡喃氧甲基，四氢吡喃氧丙基或苯基；而当R1═R2═H且R4为苯基时，R3不是丁基。发现式（I）的化合物具有抑制拓扑异构酶I的活性或作为S期或G2/M期阻滞剂的活性。
• A Series of Enediynes as Novel Inhibitors of Topoisomerase I
  作者：Chi-Fong Lin、Pei-Chen Hsieh、Wen-Der Lu、Huey-Fen Chiu、Ming-Jung Wu

  DOI：10.1016/s0968-0896(01)00081-5

  日期：2001.7

  A series of acyclic enediynes, 2-((6-substituted)-3-hexen- 1,5-diynyl)benzonitriles (8-11), display potent inhibition against topoisomerase I without the formation of active biradical intermediates and show inhibitory activity against topoisomerase I at 10 muM, which is five times that of camptothecin from the results of agarose gel electrophoresis. (C) 2001 Elsevier Science Ltd. All rights reserved.
• US7332623B2
  申请人：——

  公开号：US7332623B2

  公开（公告）日：2008-02-19