2-(2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione | 221171-45-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三嗪类
• 英文名称: 2-(2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione
• 英文别名: 2-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)-3-methylideneoxolan-2-yl]-1,2,4-triazine-3,5-dione
• CAS: 221171-45-5
• 化学式: C₉H₁₁N₃O₅
• 分子量: 241.203
• InChiKey: PPBOTHZLKFODPD-MHSYXAOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-(2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione 在 吡啶 、 甲醇 、 氯化亚砜 、 氨 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 为溶剂， 反应 6.0h， 生成 2-(2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)-5-amino-1,2,4-triazine-3(2H)-one
  参考文献：
  名称：

  Synthesis of 2′-Methylene-Substituted 5-Azapyrimidine, 6-Azapyrimidine, and 3-Deazaguanine Nucleoside Analogues as Potential Antitumor/Antiviral Agents

  摘要：

  2'-Deoxy-2'-methylene-6-azauridine (5) and 2'-deoxy-2'-methylene-6-azacytidine (8) have been synthesized via a multi-step procedure from 6-azauridine. 2'-Deoxy-2'-methylene-5-azacytidine (14a) and 2'-deoxy-2'-methylene-3-deazaguanosine (19a) and their corresponding alpha-anomers (14b and 19b) have been synthesized by the transglycosylation of 3',5'-O-(1,1,3,3- tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-methyleneu ridine (12) with silylated 5-azacytosine and silylated N2-palmitoyl-3-deazaguanine, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst in anhydrous dichloroethane, followed by separation of the isomers and deprotection of the blocking groups. These compounds were tested for cytotoxicity against B16F10, L1210, and CCRF-CEM tumor cell lines and for antiviral activity against HIV-1, HSV-1, and HSV-2.

  DOI：

  10.1080/07328319908045594
• 作为产物：
  描述：

  2-<3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-2-deoxy-2-methylene-β-D-erythro-pentofuranosyl>-1,2,4-triazine-3,5(2H,4H)-dione 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以80%的产率得到2-(2-deoxy-2-methylene-β-D-erythro-pentofuranosyl)-1,2,4-triazine-3,5(2H,4H)-dione
  参考文献：
  名称：

  Synthesis of 2′-Methylene-Substituted 5-Azapyrimidine, 6-Azapyrimidine, and 3-Deazaguanine Nucleoside Analogues as Potential Antitumor/Antiviral Agents

  摘要：

  2'-Deoxy-2'-methylene-6-azauridine (5) and 2'-deoxy-2'-methylene-6-azacytidine (8) have been synthesized via a multi-step procedure from 6-azauridine. 2'-Deoxy-2'-methylene-5-azacytidine (14a) and 2'-deoxy-2'-methylene-3-deazaguanosine (19a) and their corresponding alpha-anomers (14b and 19b) have been synthesized by the transglycosylation of 3',5'-O-(1,1,3,3- tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-methyleneu ridine (12) with silylated 5-azacytosine and silylated N2-palmitoyl-3-deazaguanine, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst in anhydrous dichloroethane, followed by separation of the isomers and deprotection of the blocking groups. These compounds were tested for cytotoxicity against B16F10, L1210, and CCRF-CEM tumor cell lines and for antiviral activity against HIV-1, HSV-1, and HSV-2.

  DOI：

  10.1080/07328319908045594

文献信息

• Synthesis of 2′-Methylene-Substituted 5-Azapyrimidine, 6-Azapyrimidine, and 3-Deazaguanine Nucleoside Analogues as Potential Antitumor/Antiviral Agents
  作者：Mao-Chin Liu、Mei-Zhen Luo、Diane E. Mozdziesz、Tai-Shun Lin、Ginger E.、Dutschman、Yung-Chi Cheng、Alan C. Sartorelli

  DOI：10.1080/07328319908045594

  日期：1999.1

  2'-Deoxy-2'-methylene-6-azauridine (5) and 2'-deoxy-2'-methylene-6-azacytidine (8) have been synthesized via a multi-step procedure from 6-azauridine. 2'-Deoxy-2'-methylene-5-azacytidine (14a) and 2'-deoxy-2'-methylene-3-deazaguanosine (19a) and their corresponding alpha-anomers (14b and 19b) have been synthesized by the transglycosylation of 3',5'-O-(1,1,3,3- tetraisopropyldisiloxane-1,3-diyl)-2'-deoxy-2'-methyleneu ridine (12) with silylated 5-azacytosine and silylated N2-palmitoyl-3-deazaguanine, respectively, in the presence of trimethylsilyl trifluoromethanesulfonate as the catalyst in anhydrous dichloroethane, followed by separation of the isomers and deprotection of the blocking groups. These compounds were tested for cytotoxicity against B16F10, L1210, and CCRF-CEM tumor cell lines and for antiviral activity against HIV-1, HSV-1, and HSV-2.