ethyl 3-[3-(C-ethylsulfanylcarbonimidoyl)phenyl]benzenecarboximidothioate | 127907-49-7

• 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: ethyl 3-[3-(C-ethylsulfanylcarbonimidoyl)phenyl]benzenecarboximidothioate
• CAS: 127907-49-7
• 化学式: C₁₈H₂₀N₂S₂
• 分子量: 328.502
• InChiKey: XCNKFRSFLONFDU-UHFFFAOYSA-N

物化性质

• 沸点：
  488.8±55.0 °C(Predicted)
• 密度：
  1.14±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  98.3
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  ethyl 3-[3-(C-ethylsulfanylcarbonimidoyl)phenyl]benzenecarboximidothioate 在 氯化铵 作用下， 以 乙醇 为溶剂， 反应 6.0h， 以38%的产率得到3,3'-diamidinobiphenyl
  参考文献：
  名称：

  S-Adenosylmethionine decarboxylase inhibitors: new aryl and heteroaryl analogs of methylglyoxal bis(guanylhydrazone)

  摘要：

  A series of 3-acylbenzamidine (amidino)hydrazones 7a-h, the corresponding (hetero)aromatic congeners 7i-p, and 3,3'-bis-amidino-biaryls 25a-e were synthesized. The hydrazones 7a-p were prepared by conversion of the corresponding acyl nitriles 1a,c-di,n-p to the imido esters 3a,c-d,i and the amidines 5a,c-d,h-i, followed by a reaction with aminoguanidine, or vice versa. Similarly, the biaryl 3,3'-dinitriles 23a-e were converted, via the imino esters 24a-c or the imino thioesters 27d-e, to the diamidines 25a-e. These new products are conformationally constrained analogues of methylglyoxal bis(guanylhydrazone)(MGBG). They are up to 100 times more potent as inhibitors of rat liver S-adenosylmethionine decarboxylase (SAMDC) and generally low potent inhibitors of rat small intestine diamine oxidase (DAO) than MGBG. Some of these SAMDC inhibitors, eg., compounds 7a, 7e, 7i, 25a, and 25d, have shown antiproliferative effects against T24 human bladder carcinoma cells. These products, whose structure-activity relationships are discussed, are of interest as potential anticancer agents and drugs for the treatment of protozoal and Pneumocystis carinii infections.

  DOI：

  10.1021/jm00053a007
• 作为产物：
  描述：

  联苯-3,3-二甲腈 在 硫化氢 、 三乙胺 作用下， 以 吡啶 、 二氯甲烷 为溶剂， 反应 24.0h， 生成 ethyl 3-[3-(C-ethylsulfanylcarbonimidoyl)phenyl]benzenecarboximidothioate
  参考文献：
  名称：

  S-Adenosylmethionine decarboxylase inhibitors: new aryl and heteroaryl analogs of methylglyoxal bis(guanylhydrazone)

  摘要：

  A series of 3-acylbenzamidine (amidino)hydrazones 7a-h, the corresponding (hetero)aromatic congeners 7i-p, and 3,3'-bis-amidino-biaryls 25a-e were synthesized. The hydrazones 7a-p were prepared by conversion of the corresponding acyl nitriles 1a,c-di,n-p to the imido esters 3a,c-d,i and the amidines 5a,c-d,h-i, followed by a reaction with aminoguanidine, or vice versa. Similarly, the biaryl 3,3'-dinitriles 23a-e were converted, via the imino esters 24a-c or the imino thioesters 27d-e, to the diamidines 25a-e. These new products are conformationally constrained analogues of methylglyoxal bis(guanylhydrazone)(MGBG). They are up to 100 times more potent as inhibitors of rat liver S-adenosylmethionine decarboxylase (SAMDC) and generally low potent inhibitors of rat small intestine diamine oxidase (DAO) than MGBG. Some of these SAMDC inhibitors, eg., compounds 7a, 7e, 7i, 25a, and 25d, have shown antiproliferative effects against T24 human bladder carcinoma cells. These products, whose structure-activity relationships are discussed, are of interest as potential anticancer agents and drugs for the treatment of protozoal and Pneumocystis carinii infections.

  DOI：

  10.1021/jm00053a007

文献信息

• S-Adenosylmethionine decarboxylase inhibitors: new aryl and heteroaryl analogs of methylglyoxal bis(guanylhydrazone)
  作者：Jaroslav Stanek、Giorgio Caravatti、Hans Georg Capraro、Pascal Furet、Helmut Mett、Peter Schneider、Urs Regenass

  DOI：10.1021/jm00053a007

  日期：1993.1

  A series of 3-acylbenzamidine (amidino)hydrazones 7a-h, the corresponding (hetero)aromatic congeners 7i-p, and 3,3'-bis-amidino-biaryls 25a-e were synthesized. The hydrazones 7a-p were prepared by conversion of the corresponding acyl nitriles 1a,c-di,n-p to the imido esters 3a,c-d,i and the amidines 5a,c-d,h-i, followed by a reaction with aminoguanidine, or vice versa. Similarly, the biaryl 3,3'-dinitriles 23a-e were converted, via the imino esters 24a-c or the imino thioesters 27d-e, to the diamidines 25a-e. These new products are conformationally constrained analogues of methylglyoxal bis(guanylhydrazone)(MGBG). They are up to 100 times more potent as inhibitors of rat liver S-adenosylmethionine decarboxylase (SAMDC) and generally low potent inhibitors of rat small intestine diamine oxidase (DAO) than MGBG. Some of these SAMDC inhibitors, eg., compounds 7a, 7e, 7i, 25a, and 25d, have shown antiproliferative effects against T24 human bladder carcinoma cells. These products, whose structure-activity relationships are discussed, are of interest as potential anticancer agents and drugs for the treatment of protozoal and Pneumocystis carinii infections.