[4,4']Bipyridinyl-2,2'-dicarboximidic acid dimethyl ester | 145276-26-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: [4,4']Bipyridinyl-2,2'-dicarboximidic acid dimethyl ester
• 英文别名: methyl 4-[2-(C-methoxycarbonimidoyl)pyridin-4-yl]pyridine-2-carboximidate
• CAS: 145276-26-2
• 化学式: C₁₄H₁₄N₄O₂
• 分子量: 270.291
• InChiKey: LMCPSNRPGBKXMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  91.9
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  [4,4']Bipyridinyl-2,2'-dicarboximidic acid dimethyl ester 在 氨 、 氯化铵 作用下， 以 甲醇 、 乙醇 为溶剂， 反应 1.0h， 生成 2,2'-diamidino-4,4'-bipyridine
  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：

  百草枯 在 高氯酸 、 水 、 sodium methylate 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 97.0h， 生成 [4,4']Bipyridinyl-2,2'-dicarboximidic acid dimethyl ester
  参考文献：
  名称：

  新型手性恶唑啉配体在 Rh(I) 催化的对映选择性氢化硅烷化中具有潜在的电荷转移效应

  摘要：

  新型 2-(4,4'-bipyridin-2-yl) 恶唑啉具有手性恶唑啉部分，从 4,4'-联吡啶开始合成，并在 N'-位选择性地单甲基化。在与铑配位后，这些缺电子配体应该在 Rh(I) 催化的对映选择性氢化硅烷化中表现出与供电子底物的电荷转移效应（见下一篇出版物）。与铑络合后，4,4'-联吡啶和吡嗪-双恶唑啉也有类似的效果。为了比较，合成了 2-(4-苯基吡啶-2-基)恶唑啉配体。制备并表征了选定配体的 Rh(I)-配合物，包括 X 射线结构分析。

  DOI：

  10.1002/(sici)1099-0682(199806)1998:6<771::aid-ejic771>3.0.co;2-y

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.
• Novel Chiral Oxazoline Ligands for Potential Charge-Transfer Effects in the Rh(I)-Catalysed Enantioselective Hydrosilylation
  作者：Henri Brunner、Reinhard Störiko、Frank Rominger

  DOI：10.1002/(sici)1099-0682(199806)1998:6<771::aid-ejic771>3.0.co;2-y

  日期：1998.6

  electron-poor ligands are supposed to exhibit charge-transfer effects with electron-donating substrates in the Rh(I)-catalysed enantioselective hydrosilylation (see next publication). Similar effects were expected from 4,4′-bipyridine- and pyrazine-bisoxazolines after complexation with rhodium. For comparison 2-(4-phenylpyridin-2-yl)oxazoline ligands were synthesised. Rh(I)-complexes of selected ligands were

  新型 2-(4,4'-bipyridin-2-yl) 恶唑啉具有手性恶唑啉部分，从 4,4'-联吡啶开始合成，并在 N'-位选择性地单甲基化。在与铑配位后，这些缺电子配体应该在 Rh(I) 催化的对映选择性氢化硅烷化中表现出与供电子底物的电荷转移效应（见下一篇出版物）。与铑络合后，4,4'-联吡啶和吡嗪-双恶唑啉也有类似的效果。为了比较，合成了 2-(4-苯基吡啶-2-基)恶唑啉配体。制备并表征了选定配体的 Rh(I)-配合物，包括 X 射线结构分析。