(1S,4R)-4-(4-Chloro-imidazo[4,5-c]pyridin-1-yl)-cyclopent-2-enol | 1026638-64-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并吡啶类
• 英文名称: (1S,4R)-4-(4-Chloro-imidazo[4,5-c]pyridin-1-yl)-cyclopent-2-enol
• 英文别名: (1S,4R)-4-(4-chloroimidazo[4,5-c]pyridin-1-yl)cyclopent-2-en-1-ol
• CAS: 1026638-64-1
• 化学式: C₁₁H₁₀ClN₃O
• 分子量: 235.673
• InChiKey: ONVRLPZYRRJOCU-JGVFFNPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  50.9
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,4R)-4-(4-Chloro-imidazo[4,5-c]pyridin-1-yl)-cyclopent-2-enol 在 吡啶 、 4-二甲氨基吡啶 、 四氧化锇 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (1S,2R,3S,4R)-4-(4-chloro-1H-imidazo<4,5-c>pyridin-1-yl)-2,3-dihydroxycyclopent-1-yl acetate
  参考文献：
  名称：

  3-Deaza- and 7-Deaza-5'-noraristeromycin and Their Antiviral Properties

  摘要：

  An enantiospecific synthesis of 3-deaza-5'noraristeromycin as its dihydrochloride ((-)-6) has been accomplished in six steps beginning with the reaction of (+)-(1R,4S)d-hydroxy-2-cyclopenten-1-yl acetate with 4-chloro-1H-imidazo[4,5-c]pyridine. The preparation of 7-deaza-5'-noraristeromycin ((-)-7) was described previously. Compounds (-)-6 and (-)-7 were evaluated for antiviral activity against a large number of viruses. Compound (-)-6 produced an antiviral activity pattern similar to 5'-noraristeromycin but was less potent. Compound (-)-6 inhibited CEM cell proliferation at a 50% inhibitory concentration of 27 mu g/mL but proved not inhibitory to HEL cell proliferation and not toxic to E(6)SM, HeLa, Vero, and MDCK cells at concentrations up to 200 mu g/mL. While (-)-6 showed inhibition of S-adenosyl-L-homocysteine (AdoHcy) hydrolase, it was less inhibitory than 5'-noraristeromcyin. Compound(-)-7 displayed no antiviral properties or inhibitory effects toward AdoHcy hydrolase.

  DOI：

  10.1021/jm00006a023
• 作为产物：
  描述：

  (1S,4R)-顺式-4-乙酰氧基-2-环戊烯-1-醇 、 4-氯咪唑[4,5-C]吡啶 在 四(三苯基膦)钯 、 sodium hydride 、 三苯基膦 作用下， 生成 (1S,4R)-4-(4-Chloro-imidazo[4,5-c]pyridin-1-yl)-cyclopent-2-enol
  参考文献：
  名称：

  3-Deaza- and 7-Deaza-5'-noraristeromycin and Their Antiviral Properties

  摘要：

  An enantiospecific synthesis of 3-deaza-5'noraristeromycin as its dihydrochloride ((-)-6) has been accomplished in six steps beginning with the reaction of (+)-(1R,4S)d-hydroxy-2-cyclopenten-1-yl acetate with 4-chloro-1H-imidazo[4,5-c]pyridine. The preparation of 7-deaza-5'-noraristeromycin ((-)-7) was described previously. Compounds (-)-6 and (-)-7 were evaluated for antiviral activity against a large number of viruses. Compound (-)-6 produced an antiviral activity pattern similar to 5'-noraristeromycin but was less potent. Compound (-)-6 inhibited CEM cell proliferation at a 50% inhibitory concentration of 27 mu g/mL but proved not inhibitory to HEL cell proliferation and not toxic to E(6)SM, HeLa, Vero, and MDCK cells at concentrations up to 200 mu g/mL. While (-)-6 showed inhibition of S-adenosyl-L-homocysteine (AdoHcy) hydrolase, it was less inhibitory than 5'-noraristeromcyin. Compound(-)-7 displayed no antiviral properties or inhibitory effects toward AdoHcy hydrolase.

  DOI：

  10.1021/jm00006a023

文献信息

• C-3 halo and 3-methyl substituted 5′-nor-3-deazaaristeromycins: Synthesis and antiviral properties
  作者：Chong Liu、Qi Chen、Minmin Yang、Stewart W. Schneller

  DOI：10.1016/j.bmc.2012.09.051

  日期：2013.1

  To expand on the antiviral properties of 5′-noraristeromycin, synthetic entry into 3-substituted 3-deaza-5′-noraristeromyin derivatives (i.e., bromo, 4; iodo, 5; chloro, 6; and, methyl, 7) has been accomplished from a common intermediate. An extensive antiviral analysis showed 7 to be basically inactive (except for weak effects against VSV) and there were no general trends among the halo compounds

  为了扩大5'-去甲诺霉素的抗病毒特性，已合成进入3取代的3-deaza-5'-去甲诺霉素衍生物（即溴4；碘5；氯6；甲基7）。从一个普通的中间体完成。广泛的抗病毒分析显示，7基本上没有活性（除了对VSV的微弱影响），并且在卤化物之间没有一般趋势（与呼肠孤病毒1和乙型流感相比）。单独地，化合物4对HCMV，VZV，HBV和VV最有利。对抗HBV，VSV，VV，乙型流感，HCMV和麻疹的产品5；并且，目标6对Punta Toro，VSV，麻疹，副流感3，甲型流感（H5N1）和乙型流感。甲基靶标7在所有病毒测定中均无活性。