1-(2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)uracil | 1051366-27-8

• 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: 1-(2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)uracil
• CAS: 1051366-27-8
• 化学式: C₁₀H₁₂N₂O₅
• 分子量: 240.216
• InChiKey: WWGREOJPJFNOAP-OOZYFLPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.66
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104.55
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  三苯基氯甲烷 、 1-(2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)uracil 在 吡啶 、 4-二甲氨基吡啶 作用下， 以75%的产率得到1-(2,3-dideoxy-6-O-trityl-α-D-erythro-hex-2-enopyranosyl)uracil
  参考文献：
  名称：

  Synthesis and molecular modelling of unsaturated exomethylene pyranonucleoside analogues with antitumor and antiviral activities

  摘要：

  This report describes the total and facile synthesis of the unsaturated keto and exomethylene pyranonucleoside analogues, 1-(2,3,4-trideoxy-4-methylene-6-O-trityl-alpha-D-glycero-hex-2-enopyranosyl)uracil (10), 1-(2,3-dideoxy-alpha-D-glycero-hex-2-enopyranosyl-4-ulose)uracil (17) and 1-(2,3,4-trideoxy-4-methylene-alpha-D-glycero-hex-2-enopyranosyl)uracil (18). Commercially available 1,2,3,4,6-penta-O-acetyl-alpha-D-mannopyranose (1) was condensed with silylated uracil, deacetylated and acetalated to afford 1-(2,3-O-isopropylidene-alpha-D-mannopyranosyl)uracil (4). Two different synthetic routes were investigated for the conversion of 4 into the olefinic derivative 1-(2,3,4-trideoxy-4-methylene-6-O-trityl-alpha-D-glycero-hex-2-enopyranosyl)uracil (10). Although the two procedures are quite similar with respect to yields and final products, the second also leads to the keto-2',3'-unsaturated analogue (17). The new analogues were evaluated for their anticancer and antiviral activities using several tumor cell lines and gastrointestinal rotavirus. All of the compounds showed direct antiviral effect against rotavirus infectivity in Caco-2 cell line. Moreover, 1-(2,3,4-trideoxy-4-methylene-6-O-trityl-alpha-D-glycero-hex-2-enopyranosyl)uracil (10) was found to be potent in MCF-7 breast carcinoma cell line. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.014
• 作为产物：
  描述：

  1-(4',6'-O-diacetyl-2',3'-dideoxy-α-D-erythro-hex-2-enopyranosyl)uracil 在 氨 作用下， 以 甲醇 为溶剂， 以64%的产率得到1-(2,3-dideoxy-α-D-erythro-hex-2-enopyranosyl)uracil
  参考文献：
  名称：

  Synthesis and molecular modelling of unsaturated exomethylene pyranonucleoside analogues with antitumor and antiviral activities

  摘要：

  This report describes the total and facile synthesis of the unsaturated keto and exomethylene pyranonucleoside analogues, 1-(2,3,4-trideoxy-4-methylene-6-O-trityl-alpha-D-glycero-hex-2-enopyranosyl)uracil (10), 1-(2,3-dideoxy-alpha-D-glycero-hex-2-enopyranosyl-4-ulose)uracil (17) and 1-(2,3,4-trideoxy-4-methylene-alpha-D-glycero-hex-2-enopyranosyl)uracil (18). Commercially available 1,2,3,4,6-penta-O-acetyl-alpha-D-mannopyranose (1) was condensed with silylated uracil, deacetylated and acetalated to afford 1-(2,3-O-isopropylidene-alpha-D-mannopyranosyl)uracil (4). Two different synthetic routes were investigated for the conversion of 4 into the olefinic derivative 1-(2,3,4-trideoxy-4-methylene-6-O-trityl-alpha-D-glycero-hex-2-enopyranosyl)uracil (10). Although the two procedures are quite similar with respect to yields and final products, the second also leads to the keto-2',3'-unsaturated analogue (17). The new analogues were evaluated for their anticancer and antiviral activities using several tumor cell lines and gastrointestinal rotavirus. All of the compounds showed direct antiviral effect against rotavirus infectivity in Caco-2 cell line. Moreover, 1-(2,3,4-trideoxy-4-methylene-6-O-trityl-alpha-D-glycero-hex-2-enopyranosyl)uracil (10) was found to be potent in MCF-7 breast carcinoma cell line. (c) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.10.014

文献信息

• Investigation of The Kinetics of Degradation of Hexopyranosylated Cytosine Nucleosides Using Liquid Chromatography
  作者：Grace N. Thoithi、Ann Van Schepdael、Roger Busson、Gerard Janssen、Arthur Van Aerschot、Piet Herdewijn、EugÈNe Roets、Jos Hoogmartens

  DOI：10.1080/15257770008033003

  日期：2000.1

  Abstract Liquid chromatography was used to follow the degradation of hexopyranosylated cytosine nucleosides in buffers of acid, neutral and alkaline pH and of constant ionic strength. The compounds were found to degrade by hydrolysis to cytosine and/or by deamination to the corresponding uracil nucleosides. Degradation in acid is influenced by the number of sugar hydroxyl groups, presence of sugar double

  摘要在酸性，中性和碱性pH值和恒定离子强度的缓冲液中，采用液相色谱法跟踪六吡喃糖基化胞嘧啶核苷的降解情况。发现该化合物通过水解成胞嘧啶和/或通过脱氨基成相应的尿嘧啶核苷而降解。酸的降解受糖羟基数量，糖双键的存在和端基异构体类型的影响。将某些化合物的稳定性与相关胸腺嘧啶核苷的稳定性进行了比较。温度研究支持在pH 1.22下水解的单分子机理。