7-(2,3-didehydro-2,3-dideoxy-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: 7-(2,3-didehydro-2,3-dideoxy-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one
• 英文别名: 2',3'-didehydro-2',3'-dideoxy-9-deazainosine；7-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3,5-dihydropyrrolo[3,2-d]pyrimidin-4-one
• 化学式: C₁₁H₁₁N₃O₃
• 分子量: 233.227
• InChiKey: CPACMINHCIRDEI-POYBYMJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  86.7
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-isobutyrylamino-7-(5-tert-butyldiphenylsilyl-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one 在 三甲基氯硅烷 、 亚硝酸特丁酯 、 四丁基氟化铵 、 氨 、 亚磷酸三乙酯 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 为溶剂， 反应 64.0h， 生成 7-(2,3-didehydro-2,3-dideoxy-β-D-ribofuranosyl)-5H-pyrrolo[3,2-d]pyrimidin-4-one
  参考文献：
  名称：

  Synthesis and Biological Evaluation of 2',3'-Didehydro-2',3'-Dideoxy-9-Deazaguanosine, a Monophosphate Prodrug and Two Analogues, 2',3'-Dideoxy-9-Deazaguanosine and 2',3'-Didehydro-2',3'-Dideoxy-9-Deazainosine

  摘要：

  2',3'-Didehydro-2',3'-dideoxy-9-deazaguanosine (1), its monaphosphate prodrug (2), and two analogues, 2',3'-dideoxy-9-deazaguanosine (3) and 2',3'-didehydro-2',3'-dideoxy-9-deazainosine (4), have been synthesized from benzoylated 9-deazaguanosine (5). Basic hydrolysis of 5, selective protection of the 2-amino and 5'-hydroxy functions with isobulyryl and silyl groups, respectively, followed by reaction with thiocarbonyldiimidazole gave the cyclic thiocarbonate, which, upon reaction with triethyl phosphite, followed 4 deprotection, afforded 1. Treatment of 1 with phenyl methoxyalaninyl phosphochloridate and N-methylimidazole gave 2. Catalytic hydrogenation of 1 gave 3. Hydrodediazoniation of 1 with tert-butyl nitrite and tris(trimethylsilyl)silane gave 4. Compounds 1-4 were found to be inactive against the human immunodeficiency virus and exhibited minimal to no cytotoxic activity against the L1210 leukemia, CCRF-CEM lymphoblastic leukemia, and B16F10 melanoma in vitro.

  DOI：

  10.1081/ncn-200051898

文献信息

• Synthesis and Biological Evaluation of 2',3'-Didehydro-2',3'-Dideoxy-9-Deazaguanosine, a Monophosphate Prodrug and Two Analogues, 2',3'-Dideoxy-9-Deazaguanosine and 2',3'-Didehydro-2',3'-Dideoxy-9-Deazainosine
  作者：Mao-Chin Liu、Mei-Zhen Luo、Diane Mozdziesz、Ginger Dutschman、Elizabeth Gullen、Yung-Chi Cheng、Alan Sartorelli

  DOI：10.1081/ncn-200051898

  日期：2005.2.1

  2',3'-Didehydro-2',3'-dideoxy-9-deazaguanosine (1), its monaphosphate prodrug (2), and two analogues, 2',3'-dideoxy-9-deazaguanosine (3) and 2',3'-didehydro-2',3'-dideoxy-9-deazainosine (4), have been synthesized from benzoylated 9-deazaguanosine (5). Basic hydrolysis of 5, selective protection of the 2-amino and 5'-hydroxy functions with isobulyryl and silyl groups, respectively, followed by reaction with thiocarbonyldiimidazole gave the cyclic thiocarbonate, which, upon reaction with triethyl phosphite, followed 4 deprotection, afforded 1. Treatment of 1 with phenyl methoxyalaninyl phosphochloridate and N-methylimidazole gave 2. Catalytic hydrogenation of 1 gave 3. Hydrodediazoniation of 1 with tert-butyl nitrite and tris(trimethylsilyl)silane gave 4. Compounds 1-4 were found to be inactive against the human immunodeficiency virus and exhibited minimal to no cytotoxic activity against the L1210 leukemia, CCRF-CEM lymphoblastic leukemia, and B16F10 melanoma in vitro.