(E)-4,4'-(but-2-ene-1,4-diylbis(oxy))dibenzonitrile | 101716-60-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (E)-4,4'-(but-2-ene-1,4-diylbis(oxy))dibenzonitrile
• 英文别名: 4,4'-but-2t-enediyldioxy-di-benzonitrile；4,4'-But-2t-endiyldioxy-di-benzonitril；4-[(E)-4-(4-cyanophenoxy)but-2-enoxy]benzonitrile
• CAS: 101716-60-3
• 化学式: C₁₈H₁₄N₂O₂
• 分子量: 290.321
• InChiKey: WSEJGSYXBRTHMO-OWOJBTEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  66
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (E)-4,4'-(but-2-ene-1,4-diylbis(oxy))dibenzonitrile 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 以59%的产率得到(E)-4,4'-(but-2-ene-1,4-diylbis(oxy))dibenzimidamide
  参考文献：
  名称：

  Discovery of decamidine as a new and potent PRMT1 inhibitor

  摘要：

  这份报告介绍了十甲胺作为蛋白质精氨酸甲基转移酶1（PRMT1）的有效抑制剂的合成和评价。

  DOI：

  10.1039/c6md00573j
• 作为产物：
  描述：

  反式-1,4-二氯-2-丁烯 、 4-羟基苯甲腈 在 乙醇 、 sodium 作用下， 生成 (E)-4,4'-(but-2-ene-1,4-diylbis(oxy))dibenzonitrile
  参考文献：
  名称：

  Pentamidine Congeners. 2. 2-Butene-Bridged Aromatic Diamidines and Diimidazolines as Potential Anti-Pneumocystis carinii Pneumonia Agents

  摘要：

  We have synthesized cis and trans geometric isomers 1-8 as semirigid congeners of pentamidine. Compounds 1-4 were more potent than pentamidine in treating Pneumocystis carinii pneumonia in immunosuppressed rats. These compounds also demonstrated no clinical toxicity or histopathologic abnormalities. Introduction of methoxy substituents meta to the amidine or imidazoline groups of the phenyl rings as in compounds 5-8 generally resulted in compounds with decreased anti-P. carinii activity and increased toxicity to the host. Compounds 1-4 were evaluated as DNA binders. These compounds showed greater affinity for poly(dA).poly(dT) than for calf thymus DNA. The cis isomers, 1 and 2, demonstrated greater affinity for DNA than their trans counterparts 3 and 4. This difference in DNA binding affinity, however, did not reflect in a corresponding difference in the anti-P. carinii activity of these compounds.

  DOI：

  10.1021/jm00052a014

文献信息

• 316. The search for chemotherapeutic amidines. Part XIII. αω-Di-p-amidinophenoxy-alkenes and -alkynes
  作者：J. N. Ashley、R. D. MacDonald

  DOI：10.1039/jr9570001668

  日期：——
• Discovery of decamidine as a new and potent PRMT1 inhibitor
  作者：Jing Zhang、Kun Qian、Chunli Yan、Maomao He、Brenson A. Jassim、Ivaylo Ivanov、Yujun George Zheng

  DOI：10.1039/c6md00573j

  日期：——

  This report presents the synthesis and evaluation of compound decamidine as a potent inhibitor for protein arginine methyltransferase 1 (PRMT1).

  这份报告介绍了十甲胺作为蛋白质精氨酸甲基转移酶1（PRMT1）的有效抑制剂的合成和评价。
• Pentamidine Congeners. 2. 2-Butene-Bridged Aromatic Diamidines and Diimidazolines as Potential Anti-Pneumocystis carinii Pneumonia Agents
  作者：Isaac O. Donkor、Richard R. Tidwell、Susan K. Jones

  DOI：10.1021/jm00052a014

  日期：1994.12

  We have synthesized cis and trans geometric isomers 1-8 as semirigid congeners of pentamidine. Compounds 1-4 were more potent than pentamidine in treating Pneumocystis carinii pneumonia in immunosuppressed rats. These compounds also demonstrated no clinical toxicity or histopathologic abnormalities. Introduction of methoxy substituents meta to the amidine or imidazoline groups of the phenyl rings as in compounds 5-8 generally resulted in compounds with decreased anti-P. carinii activity and increased toxicity to the host. Compounds 1-4 were evaluated as DNA binders. These compounds showed greater affinity for poly(dA).poly(dT) than for calf thymus DNA. The cis isomers, 1 and 2, demonstrated greater affinity for DNA than their trans counterparts 3 and 4. This difference in DNA binding affinity, however, did not reflect in a corresponding difference in the anti-P. carinii activity of these compounds.