4-chloro-7-fluoro-1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridine | 405231-10-9

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑[4，5-c]吡啶核糖核苷和核糖核苷酸
• 英文名称: 4-chloro-7-fluoro-1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridine
• 英文别名: 4-Chloro-7-fluoro-1-(beta-D-ribofuranosyl)imidazo[4,5-c]pyridine；(2R,3R,4S,5R)-2-(4-chloro-7-fluoroimidazo[4,5-c]pyridin-1-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 405231-10-9
• 化学式: C₁₁H₁₁ClFN₃O₄
• 分子量: 303.677
• InChiKey: IERLTEXKXWXSEQ-MGUDNFKCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-chloro-7-fluoro-1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridine 在 镍 氢气 、 肼 作用下， 以 水 为溶剂， 反应 9.0h， 生成 4-amino-7-fluoro-1-(β-D-ribofuranosyl)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
• 作为产物：
  描述：

  2-氯-4-硝基-5-氟吡啶氮氧化物 在 镍 硫酸氢铵 、 硫酸 、 氢气 、 sodium methylate 、 potassium nitrate 、 六甲基二硅氮烷 作用下， 以 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、275.79 kPa 条件下， 反应 5.5h， 生成 4-chloro-7-fluoro-1-(β-D-ribofuranosyl)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

文献信息

• Novel nucleosides and related processes, pharmaceutical compositions and methods
  申请人：——

  公开号：US20040116362A1

  公开（公告）日：2004-06-17

  The invention provides novel nucleosides and related processes, pharmaceutical compositions, and methods. The novel nucleosides are useful in a wide variety of antiviral, antineoplastic, and antibacterial applications. Preferred embodiments of the instant invention include novel 2 halogen-substituted, 3 halogen-substituted, and 2′,3′dihalogen-substituted analogues of 3-deazaadenosine, and novel 3 halogen-substituted analogues of 3-deazaguanosine. Compounds of the instant invention, including 4-Amino-6-fluoro-1-(&bgr;-D-ribofuranosyl)imidazo[4,5-c]pyridine and 6-Amino-7-bromo-1,5-dihydro-1-&bgr;- D -ribofuranosylimidazo[4,5-c]pyridin-4-one, have exhibited potent antiviral and anticancer activity in vitro. The compounds are also useful in the concomitant treatment of bacterial infections associated with viral infections such as AIDS.

  该发明提供了新颖的核苷和相关的工艺、药物组合和方法。这些新颖的核苷在抗病毒、抗肿瘤和抗菌应用中非常有用。该发明的首选实施例包括新型的2卤代、3卤代和2′,3′二卤代的3-去氨腺苷类似物，以及新型的3卤代的3-去氨鸟苷类似物。该发明的化合物，包括4-氨基-6-氟-1-(&bgr;-D-核糖呋喃基)咪唑[4,5-c]吡啶和6-氨基-7-溴-1,5-二氢-1-&bgr;-D-核糖基咪唑[4,5-c]吡啶-4-酮，在体外表现出强效的抗病毒和抗癌活性。这些化合物也在同时治疗与艾滋病等病毒感染相关的细菌感染方面非常有用。
• Nucleoside derivatives for treating hepatitis C virus infection
  申请人：——

  公开号：US20040063658A1

  公开（公告）日：2004-04-01

  Disclosed are compounds, compositions and methods for treating hepatitis C virus infections.

  本发明涉及用于治疗丙型肝炎病毒感染的化合物、组合物和方法。
• Nucleosides and related processes, pharmaceutical compositions and methods
  申请人：Sartorelli Alan C.

  公开号：US06960568B2

  公开（公告）日：2005-11-01

  The invention provides novel nucleosides and related processes, pharmaceutical compositions, and methods. The novel nucleosides are useful in a wide variety of antiviral, antineoplastic, and antibacterial applications. Preferred embodiments of the instant invention include novel 2 halogen-substituted, 3 halogen-substituted, and 2′,3′dihalogen-substituted analogues of 3-deazaadenosine, and novel 3 halogen-substituted analogues of 3-deazaguanosine. Compounds of the instant invention, including 4-Amino-6-fluoro-1-(β-D-ribofuranosyl)imidazo[4,5-c]pyridine and 6-Amino-7-bromo-1,5-dihydro-1-β- D -ribofuranosylimidazo[4,5-c]pyridin-4-one, have exhibited potent antiviral and anticancer activity in vitro. The compounds are also useful in the concomitant treatment of bacterial infections associated with viral infections such as AIDS.

  本发明提供了新型核苷和相关的工艺、制药组合物和方法。这些新型核苷在广泛的抗病毒、抗肿瘤和抗菌应用中非常有用。本发明的优选实施例包括3-去氮腺苷的新型2卤素取代、3卤素取代和2'、3'二卤素取代类似物，以及3-去氮鸟嘌呤核苷的新型3卤素取代类似物。本发明的化合物，包括4-氨基-6-氟-1-(β-D-核糖呋喃基)咪唑[4,5-c]吡啶和6-氨基-7-溴-1,5-二氢-1-β-D-核糖呋喃基咪唑[4,5-c]吡啶-4-酮，在体外表现出强大的抗病毒和抗癌活性。这些化合物也可用于与病毒感染相关的细菌感染的联合治疗，如艾滋病。
• NUCLEOSIDE DERIVATIVES FOR TREATING HEPATITIS C VIRUS INFECTION
  申请人：GENELABS TECHNOLOGIES, INC.

  公开号：EP1501850A2

  公开（公告）日：2005-02-02
• US6960568B2
  申请人：——

  公开号：US6960568B2

  公开（公告）日：2005-11-01