2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyloxy>-1,3-propanediyl dibenzoate | 103824-50-6

• 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-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyloxy>-1,3-propanediyl dibenzoate
• 英文别名: 1-[2-benzoyloxy-1-(benzoyl-oxymethyl)ethoxymethyl]cytosine；2-[(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyloxy]-1,3-propanediyl dibenzoate；[2-[(4-Amino-2-oxopyrimidin-1-yl)methoxy]-3-benzoyloxypropyl] benzoate
• CAS: 103824-50-6
• 化学式: C₂₂H₂₁N₃O₆
• 分子量: 423.425
• InChiKey: AKUULGFZFSUFDO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  31
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyloxy>-1,3-propanediyl dibenzoate 在 sodium hydroxide 、 碳酸氢钠 作用下， 以 四氢呋喃 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 28.0h， 生成 <(4-(((benzyloxy)carbonyl)amino)-1,2-dihydro-2-oxo-1-pyrimidinyl)methoxy>-1,3-propanediyl bis-L-valinate
  参考文献：
  名称：

  An Efficient Synthesis of 2-[(4-Amino∼1,2-dihyro-2-oxo-1- pyrimidinyl)methoxyi-l,3-propanediyl-di-L-valinate an Anti-cytomegalovirus Agent

  摘要：

  An efficient synthesis for large scale preparation of the titled compound, a prodrug for the anti-HCMV agent 1-[2-hydroxy-1-(hydroxymethyl)ethoxyl]cytosine, 9, has been developed. The product of each step is easily purified by either distillation or recrystallization and the final product is obtained in a high overall yield.

  DOI：

  10.1080/15257779508009494
• 作为产物：
  描述：

  2-(甲氧基甲氧基)-1,3-丙烷二基二苯甲酸酯 在 三甲基溴硅烷 、 硫酸 作用下， 以 二氯甲烷 为溶剂， 生成 2-<(4-amino-1,2-dihydro-2-oxo-1-pyrimidinyl)methyloxy>-1,3-propanediyl dibenzoate
  参考文献：
  名称：

  An Efficient Synthesis of 2-[(4-Amino∼1,2-dihyro-2-oxo-1- pyrimidinyl)methoxyi-l,3-propanediyl-di-L-valinate an Anti-cytomegalovirus Agent

  摘要：

  An efficient synthesis for large scale preparation of the titled compound, a prodrug for the anti-HCMV agent 1-[2-hydroxy-1-(hydroxymethyl)ethoxyl]cytosine, 9, has been developed. The product of each step is easily purified by either distillation or recrystallization and the final product is obtained in a high overall yield.

  DOI：

  10.1080/15257779508009494

文献信息

• Effect of Various Pyrimidines Possessing the 1-[(2-Hydroxy-1-(hydroxymethyl)ethoxy)methyl] Moiety, Able To Mimic Natural 2‘-Deoxyribose, on Wild-type and Mutant Hepatitis B Virus Replication
  作者：Rakesh Kumar、Wassila Semaine、Monika Johar、D. Lorne J. Tyrrell、Babita Agrawal

  DOI：10.1021/jm060102l

  日期：2006.6.1

  glycosyl moiety at the N-1 position, that have the ability to mimic the natural 2'-deoxyribosyl moiety. Some of these potential antiviral compounds included variations at both C-5 and C-6 positions of the uracil base. Other variations of the uracil derivatives were the 6-aza congeners. 4-Amino and 4-methoxy pyrimidine derivatives were also made. Compounds in which the base moiety was substituted by 5-chloro-

  乙型肝炎病毒（HBV）是全世界慢性肝病的最常见原因。由于长期使用和停止治疗后病毒DNA反弹，对临床抗HBV药物拉米夫定产生的耐药性已成为当前疗法的主要挫折。我们合成了一系列嘧啶核苷，它们在C-5位具有多个取代基，在N-1位具有1-[（（2-羟基-1-（羟甲基）乙氧基）甲基]柔性无环糖基部分，具有模仿天然2'-脱氧核糖基部分的能力。这些潜在的抗病毒化合物中的一些在尿嘧啶碱基的C-5和C-6位置均包含变异。尿嘧啶衍生物的其他变体是6-氮杂同源物。还制备了4-氨基和4-甲氧基嘧啶衍生物。碱基部分被5-氯-（25），5-（2-溴乙烯基）-（32）或5-溴-6-甲基-（37）基团取代的化合物对鸭HBV具有显着的活性，野生型人HBV（2.2.15个细胞）和抗拉米夫定的HBV，其中包含单突变和双突变。直至测试的最高浓度，在宿主HepG2和Vero细胞中均未见细胞毒性。与相应的嘌呤核苷更昔洛韦相比，化合物
• Antiviral compounds, treatment and formulations
  申请人：THE WELLCOME FOUNDATION LIMITED

  公开号：EP0167385B1

  公开（公告）日：1992-03-18
• Efficient synthesis of 1,2-seco and 1,2-seco 2-nor pyrimidine and purine nucleosides
  作者：Muhammad Azymah、Claude Chavis、Marc Lucas、Jean-Louis Imbach

  DOI：10.1016/s0040-4039(01)93332-5

  日期：——
• AZYMAH, MUHAMMAD;CHAVIS, CLAUDE;LUCAS, MARC;IMBACH, JEAN-LOUIS, TETRAHEDRON LETT., 30,(1989) N5, C. 6165-6168
  作者：AZYMAH, MUHAMMAD、CHAVIS, CLAUDE、LUCAS, MARC、IMBACH, JEAN-LOUIS

  DOI：——

  日期：——
• An Efficient Synthesis of 2-[(4-Amino∼1,2-dihyro-2-oxo-1- pyrimidinyl)methoxyi-l,3-propanediyl-di-L-valinate an Anti-cytomegalovirus Agent
  作者：Nabih Ghal、Barbara Johnston、Lilia Beauchamp、Taj Naseree、Tracy Scott、Roy Flanagan、Martha Rodriguez

  DOI：10.1080/15257779508009494

  日期：1995.9

  An efficient synthesis for large scale preparation of the titled compound, a prodrug for the anti-HCMV agent 1-[2-hydroxy-1-(hydroxymethyl)ethoxyl]cytosine, 9, has been developed. The product of each step is easily purified by either distillation or recrystallization and the final product is obtained in a high overall yield.