7-chloro-4,6-difluoroimidazo[4,5-c]pyridine | 405230-96-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 7-chloro-4,6-difluoroimidazo[4,5-c]pyridine
• 英文别名: 3-chloro-2,6-difluoro-3-deazapurine；7-Chloro-4,6-difluoro-1H-imidazo[4,5-C]pyridine；7-chloro-4,6-difluoro-3H-imidazo[4,5-c]pyridine
• CAS: 405230-96-8
• 化学式: C₆H₂ClF₂N₃
• 分子量: 189.552
• InChiKey: HYMLODBAMPTLDN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  7-chloro-4,6-difluoroimidazo[4,5-c]pyridine 在 硫酸氢铵 、 氨 、 六甲基二硅氮烷 作用下， 以 乙醇 为溶剂， 生成 4-amino-7-chloro-6-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：

  4-氨基-3,5-二氯-2,6-二氟吡啶 在 palladium on activated charcoal 、 镍 硫酸 、 氢气 、 potassium nitrate 、 三乙胺 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、344.74 kPa 条件下， 反应 18.0h， 生成 7-chloro-4,6-difluoroimidazo[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。
• Novel halogenated 3-deazapurine, 7-deazapurine and alkylated 9-deazapurine derivatives of l-ascorbic or imino-l-ascorbic acid: Synthesis, antitumour and antiviral activity evaluations
  作者：Maja Stipković Babić、Damjan Makuc、Janez Plavec、Tamara Martinović、Sandra Kraljević Pavelić、Krešimir Pavelić、Robert Snoeck、Graciela Andrei、Dominique Schols、Karlo Wittine、Mladen Mintas

  DOI：10.1016/j.ejmech.2015.08.008

  日期：2015.9

  Keeping the potential synergy of biological activity of synthetic anomalous derivatives of deazapurines and L-ascorbic acid (L-AA) in mind, we have synthesized new 3-, 7- and 9-deazapurine derivatives of L-ascorbic (1-4, 8-10, 13-15) and imino-L-ascorbic acid (5-7, 11, 12, 16-19). These novel compounds were evaluated for their cytostatic and antiviral activity in vitro against a panel of human malignant tumour cell lines and normal murine fibroblasts (3T3). Among all evaluated compounds, the 9-deazapurine derivative of L-AA (13) exerted the most potent inhibitory activity on the growth of CEM/0 cells (IC50 = 4.1 +/- 1.8 mu M) and strong antiproliferative effect against L1210/0 (IC50 = 4.7 +/- 0.1 mu M) while the 9-deazahypoxanthine derivative of L-AA (15) showed the best effect against HeLa cells (IC50 = 5.6 +/- 1.3 mu M) and prominent effect on L1210/0 (IC50 = 4.5 +/- 0.5 mu M). Furthermore, the 9-deazapurine derivative disubstituted with two imino-L-AA moieties (18) showed the best activity against L1210/0 tumour cells (IC50 = 4.4 +/- 0.3 mu M) and the most pronounced antiproliferative effects against MiaPaCa-2 cells (IC50 = 5.7 +/- 0.2 mu M). All these compounds showed selective cytostatic effect on tumour cell lines in comparison with embryonal murine fibroblasts (3T3). When evaluating their antiviral activity, the 3-deazapurine derivative of L-AA (3) exhibited the highest activity against both laboratory-adapted strains of human cytomegalovirus (HCMV) (AD-169 and Davis) with EC50 values comparable to those of the well-known anti-HCMV drug ganciclovir and without cytotoxic effects on normal human embryonal lung (HEL) cells. (C) 2015 Elsevier Masson SAS. All rights reserved.
• US6960568B2
  申请人：——

  公开号：US6960568B2

  公开（公告）日：2005-11-01
• SYNTHESIS OF HALOGEN-SUBSTITUTED 3-DEAZAADENOSINE AND 3-DEAZAGUANOSINE ANALOGUES AS POTENTIAL ANTITUMOR/ANTIVIRAL AGENTS
  作者：Mao-Chin Liu、Mei-Zhen Luo、Diane Mozdziesz、Tai-Shun Lin?1、Ginger Dutschman、Elizabeth Gullen、Yung-Chi Cheng、Alan Sartorelli

  DOI：10.1081/ncn-100108327

  日期：——

  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.