5-(chloroethyl)-1-(3,5-di-O-p-toluoyl-2-deoxyribofuraanosyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2-one | 194596-15-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: 5-(chloroethyl)-1-(3,5-di-O-p-toluoyl-2-deoxyribofuraanosyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2-one
• 英文别名: 5-(2-chloroethyl) 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-ribofuranosyl]-4-(1H-1,2,4-triazol-1-yl)pyrimidin-1(1H)-one；[(2R,3S,5R)-5-[5-(2-chloroethyl)-2-oxo-4-(1,2,4-triazol-1-yl)pyrimidin-1-yl]-3-(4-methylbenzoyl)oxyoxolan-2-yl]methyl 4-methylbenzoate
• CAS: 194596-15-1
• 化学式: C₂₉H₂₈ClN₅O₆
• 分子量: 578.024
• InChiKey: LIXSAHZWXSXNRD-ISJGIBHGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  41
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(chloroethyl)-1-(3,5-di-O-p-toluoyl-2-deoxyribofuraanosyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2-one 在 肼 作用下， 以 吡啶 、 乙腈 为溶剂， 反应 4.0h， 生成 8-(2-chloroethyl)-6-(3,5-di-O-p-toluoyl-2-deoxy-β-D-ribofuranosyl)-3-methyl-1,2,4-triazolo[4,3-c]pyrimidin-5-one
  参考文献：
  名称：

  The Syntheses of Pyrimido-pyridazinone and Pyrrolidino-pyrimidinone 2′-Deoxynucleoside Derivatives

  摘要：

  Nucleosides that have ambivalent tautomeric properties have value in a variety of nucleic-acid hybridisation applications and as mutagenic agents. We describe here synthetic studies directed to stable derivatives based on N-4-aminocytosine. Treatment of the 5-(chloroethyl)-4-(triazol-1-yl)pyrimidine-nucleoside derivative 1 with benzylhydrazine leads to the formation of the 6,6-bicyclic pyrimido-pyridazin-7-one 6, in addition to the 5,6-bicyclic derivative 7. The 6,6-bicyclic benzyl derivative 6 was converted to its 5'-triphosphate for studies with DNA polymerases. Reaction of the triazole 1 with hydrazine, followed by acetylation,led to the desired acetylated 6,6-bicyclic derivative 12. However, the latter compound undergoes acyl migration followed by ring contraction to the 5,6-bicyclic compound 13 on treatment with base.

  DOI：

  10.1002/1522-2675(20000809)83:8<1693::aid-hlca1693>3.0.co;2-e
• 作为产物：
  描述：

  1H-1,2,4-三唑 、 5-(2-chloroethyl)-1-(2-deoxy-3,5-di-O-p-toluoyl-β-D-erythro-pentofuranosyl)-1H,3H-pyrimidine-2,4-dione 在 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 以86%的产率得到5-(chloroethyl)-1-(3,5-di-O-p-toluoyl-2-deoxyribofuraanosyl)-4-(1,2,4-triazol-1-yl)pyrimidin-2-one
  参考文献：
  名称：

  The Synthesis of BicyclicN4-Amino-2′-deoxycytidine Derivatives

  摘要：

  Nucleosides which have ambivalent tautomeric properties have value in a variety of nucleic acid hybridization applications, and as mutagenic agents. We describe here synthetic studies directed to stable derivatives of this kind of nucleoside based on N-4-aminocytosine. Treatment of the 4-(1H-1,2,4-triazol-1-yl)-5-(chloroethyl)pyrimidinone nucleoside derivative 5 with hydrazine leads to formation of the 6,6-bicyclic pyrimido-pyridazin-7-one 3, and with methylhydrazine to the corresponding fixed tautomeric I-methyl derivative 7 (Scheme 1). If these cyclization reactions are carried out in the presence of a base, the 6-ring bicyclic derivatives undergo rearrangement to their corresponding 5-ring pyrrolo-pyrimidin-2-one analogues 8 (Scheme 2). In the reaction of the triazolyl derivative 5 with 1-[(benzyloxy)carbonyl]-2-methylhydrazine, spontaneous cyclization gives the 5-ring derivative 13 related to 8 rather than the open-chain product 12 (Scheme 4). Reaction of an acetylated analogue of triazolyl derivative 5 with 1,1-dimethylhydrazine gives rise to some of the open-chain product 9, but it too cyclizes to a product that we have assigned the structure of the 6,6-ring quaternary ammonium salt 11 (Scheme 3).

  DOI：

  10.1002/(sici)1522-2675(19991110)82:11<2028::aid-hlca2028>3.0.co;2-e