1-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,6-difluoro-1H-imidazo[4,5-c]pyridine | 405231-02-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物
• 英文名称: 1-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,6-difluoro-1H-imidazo[4,5-c]pyridine
• 英文别名: 1-[(3S,4R,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolan-2-yl]-4,6-difluoroimidazo[4,5-c]pyridine
• CAS: 405231-02-9
• 化学式: C₃₂H₂₉F₂N₃O₄
• 分子量: 557.597
• InChiKey: MSTLSDPPFZNQGH-LZYAHJOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.99
• 重原子数：
  41.0
• 可旋转键数：
  11.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  67.63
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  1-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,6-difluoro-1H-imidazo[4,5-c]pyridine 在 palladium dihydroxide 、 氨 、 环己烯 作用下， 以 乙醇 为溶剂， 生成 4-amino-6-fluoro-1-α-D-arabinofuranosylimidazo[4,5-c]pyridine
  参考文献：
  名称：

  SYNTHESIS OF HALOGEN-SUBSTITUTED 3-DEAZAADENOSINE AND 3-DEAZAGUANOSINE ANALOGUES AS POTENTIAL ANTITUMOR/ANTIVIRAL AGENTS

  摘要：

  Various 2-halogen-substituted analogues (38, 39, 43 and 44), 3-halogen-substituted analogues (51 and 52), and 2',3'-dihalogen-substituted analogues (57-60) of 3-deazaadenosine and 3-halogen-substituted analogues (61 and 62) of 3-deazaguanosine have been synthesized as potential anticancer and/or antiviral agents. Among these compounds, 3-deaza-3-bromoguanosine (62) showed significant cytotoxicity against L1210, P388, CCRF-CEM and B16F10 cell lines in vitro, producing IC50 values of 3, 7, 9 and 7 muM, respectively. Several 3-deazaadenosine analogues (38, 51, 57 and 59) showed moderate to weak activity against hepatitis B virus.

  DOI：

  10.1081/ncn-100108327
• 作为产物：
  描述：

  4-氨基-2,6-二氟吡啶 在 镍 硫酸氢铵 、 三氟甲磺酸三甲基硅酯 、 硫酸 、 氢气 、 potassium nitrate 、 六甲基二硅氮烷 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 1-((3S,4R,5R)-3,4-Bis-benzyloxy-5-benzyloxymethyl-tetrahydro-furan-2-yl)-4,6-difluoro-1H-imidazo[4,5-c]pyridine
  参考文献：
  名称：

  SYNTHESIS OF HALOGEN-SUBSTITUTED 3-DEAZAADENOSINE AND 3-DEAZAGUANOSINE ANALOGUES AS POTENTIAL ANTITUMOR/ANTIVIRAL AGENTS

  摘要：

  Various 2-halogen-substituted analogues (38, 39, 43 and 44), 3-halogen-substituted analogues (51 and 52), and 2',3'-dihalogen-substituted analogues (57-60) of 3-deazaadenosine and 3-halogen-substituted analogues (61 and 62) of 3-deazaguanosine have been synthesized as potential anticancer and/or antiviral agents. Among these compounds, 3-deaza-3-bromoguanosine (62) showed significant cytotoxicity against L1210, P388, CCRF-CEM and B16F10 cell lines in vitro, producing IC50 values of 3, 7, 9 and 7 muM, respectively. Several 3-deazaadenosine analogues (38, 51, 57 and 59) showed moderate to weak activity against hepatitis B virus.

  DOI：

  10.1081/ncn-100108327