4-[5-(methyloxycarbonyl)-pentylamino]-1-(benzyloxy)-2(1H)-pyrimidinone | 189497-16-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-[5-(methyloxycarbonyl)-pentylamino]-1-(benzyloxy)-2(1H)-pyrimidinone
• 英文别名: 4-[5-(methoxycarbonyl)pentylamino]-1-(benzyloxy)pyrimidin-2(1H)-one；4-{[5-(methoxycarbonyl)pentyl]amino}-1-(benzyloxy)-2(1H)-pyrimidinone；Methyl 6-[(2-oxo-1-phenylmethoxypyrimidin-4-yl)amino]hexanoate
• CAS: 189497-16-3
• 化学式: C₁₈H₂₃N₃O₄
• 分子量: 345.398
• InChiKey: XXXPEOOHQPDMKZ-UHFFFAOYSA-N

物化性质

• 熔点：
  150-152 °C(Solv: methanol (67-56-1); ethyl ether (60-29-7))
• 沸点：
  465.3±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  25
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  80.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-[5-(methyloxycarbonyl)-pentylamino]-1-(benzyloxy)-2(1H)-pyrimidinone 在 sodium hydroxide 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.0h， 生成 4-[5-(carboxy)pentylamino]-1-(benzyloxy)pyrimidin-2(1H)-one-O-succinimide
  参考文献：
  名称：

  Masuda, Takeshi; Hayashi, Jun-Ichiro; Tamagaki, Seizo, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 1, p. 161 - 167

  摘要：

  DOI：
• 作为产物：
  描述：

  N-(苄氧基)脲 在 sodium 、 三乙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 为溶剂， 反应 92.0h， 生成 4-[5-(methyloxycarbonyl)-pentylamino]-1-(benzyloxy)-2(1H)-pyrimidinone
  参考文献：
  名称：

  Novel Iron Sequestering Agents:  Synthesis and Iron-Chelating Properties of Hexadentate Ligands Composed of 1-Hydroxy-2(1H)-pyrimidinone, ω-Amino Carboxylic Acid, and Tris(2-aminoethyl)amine

  摘要：

  Novel heterocyclic hexadentate ligands (3HOPY(n): n = 5-7), in which three units of 1-hydroxy-2(1H)-pyrimidinone are linked to tris(2-aminoethyl)amine through an amide bond by an alkyl chain, were synthesized, and their iron-chelating properties were investigated. The stability of their iron complexes (25 to 27 in log K) was significantly larger than that of pyrazinone-containing ligands by virtue of higher pK(a) values. On kinetic evaluation of iron removal from human transferrin, 3HOPY(5) showed remarkable efficiency over five times as much as commercially available desferrioxamine B. The conformational analysis of the corresponding Ga(III) complex of Fe(opy(5)) by H-1 NMR and by MM and MD calculations are also discussed.

  DOI：

  10.1021/jo961901m

文献信息

• New hydroxypyrimidinone-containing sulfonamides as carbonic anhydrase inhibitors also acting as MMP inhibitors
  作者：M. Alexandra Esteves、Osvaldo Ortet、Anabela Capelo、Claudiu T. Supuran、Sérgio M. Marques、M. Amélia Santos

  DOI：10.1016/j.bmcl.2010.04.109

  日期：2010.6

  (BSA) derivatives bearing a hydroxypyrimidinone (HPM) moiety were synthesized and investigated for their inhibitory activity against several carbonic anhydrase (CA, EC 4.2.1.1) isozymes. They all revealed to be very potent inhibitors (nanomolar order) of the cytosolic CA I and II isozymes, but especially of the transmembrane, tumor-associated CA IX isozyme, a beneficial feature for a potential antitumor

  合成了一组带有羟基嘧啶酮（HPM）部分的苯磺酰胺（BSA）衍生物，并研究了它们对几种碳酸酐酶（CA，EC 4.2.1.1）同工酶的抑制活性。它们都显示出是胞质CA I和II同工酶的非常有效的抑制剂（纳摩尔级），但尤其是跨膜的，与肿瘤相关的CA IX同工酶，对这些化合物具有潜在的抗肿瘤作用是有益的。旨在改善CA抑制特异性和增强其基质金属蛋白酶（MMP）抑制活性的进一步结构优化也可能导致具有抗肿瘤剂双重作用机理的新型化合物。
• Novel Iron Sequestering Agents:  Synthesis and Iron-Chelating Properties of Hexadentate Ligands Composed of 1-Hydroxy-2(1<i>H</i>)-pyrimidinone, ω-Amino Carboxylic Acid, and Tris(2-aminoethyl)amine
  作者：Junko Ohkanda、Jun Kamitani、Takeshi Tokumitsu、Yoko Hida、Takeo Konakahara、Akira Katoh

  DOI：10.1021/jo961901m

  日期：1997.5.1

  Novel heterocyclic hexadentate ligands (3HOPY(n): n = 5-7), in which three units of 1-hydroxy-2(1H)-pyrimidinone are linked to tris(2-aminoethyl)amine through an amide bond by an alkyl chain, were synthesized, and their iron-chelating properties were investigated. The stability of their iron complexes (25 to 27 in log K) was significantly larger than that of pyrazinone-containing ligands by virtue of higher pK(a) values. On kinetic evaluation of iron removal from human transferrin, 3HOPY(5) showed remarkable efficiency over five times as much as commercially available desferrioxamine B. The conformational analysis of the corresponding Ga(III) complex of Fe(opy(5)) by H-1 NMR and by MM and MD calculations are also discussed.
• Masuda, Takeshi; Hayashi, Jun-Ichiro; Tamagaki, Seizo, Journal of the Chemical Society. Perkin Transactions 2 (2001), 2000, # 1, p. 161 - 167
  作者：Masuda, Takeshi、Hayashi, Jun-Ichiro、Tamagaki, Seizo

  DOI：——

  日期：——