methyl 1-(2-cyano-4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate | 1195973-28-4

• 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: methyl 1-(2-cyano-4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate
• 英文别名: Methyl 1-[(2-cyano-4-fluorophenyl)methyl]pyrrolo[2,3-c]pyridine-5-carboxylate
• CAS: 1195973-28-4
• 化学式: C₁₇H₁₂FN₃O₂
• 分子量: 309.3
• InChiKey: MEMNRAOBURSNSF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  67.9
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 1-(2-cyano-4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate 在 盐酸羟胺 、 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 反应 16.0h， 以28%的产率得到1-(2-cyano-4-fluorobenzyl)-N-hydroxy-1H-pyrrolo[2,3-c]pyridine-5-carboxamide
  参考文献：
  名称：

  Azaindole Hydroxamic Acids are Potent HIV-1 Integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) is one of three enzymes encoded by the HIV genome and is essential for viral replication. Recently, HIV-1 IN inhibitors have emerged as a new promising class of therapeutics. Herein, we report the discovery of azaindole carboxylic acids and azaindole hydroxamic acids as potent inhibitors of the HIV-1 IN enzyme and their structure-activity relationships. Several 4-fluorobenzyl substituted azaindole hydroxamic acids showed potent antiviral activities in cell-based assays and offered a structurally simple scaffold for the development of novel HIV-1 IN inhibitors.

  DOI：

  10.1021/jm900862n
• 作为产物：
  描述：

  1H-吡咯并[2,3-c]吡啶-5-羧酸甲酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium hydride 作用下， 以 四氢呋喃 、 mineral oil 为溶剂， 反应 2.25h， 生成 methyl 1-(2-cyano-4-fluorobenzyl)-1H-pyrrolo[2,3-c]pyridine-5-carboxylate
  参考文献：
  名称：

  Azaindole Hydroxamic Acids are Potent HIV-1 Integrase Inhibitors

  摘要：

  HIV-1 integrase (IN) is one of three enzymes encoded by the HIV genome and is essential for viral replication. Recently, HIV-1 IN inhibitors have emerged as a new promising class of therapeutics. Herein, we report the discovery of azaindole carboxylic acids and azaindole hydroxamic acids as potent inhibitors of the HIV-1 IN enzyme and their structure-activity relationships. Several 4-fluorobenzyl substituted azaindole hydroxamic acids showed potent antiviral activities in cell-based assays and offered a structurally simple scaffold for the development of novel HIV-1 IN inhibitors.

  DOI：

  10.1021/jm900862n

文献信息

• Azaindole Hydroxamic Acids are Potent HIV-1 Integrase Inhibitors
  作者：Michael B. Plewe、Scott L. Butler、Klaus R. Dress、Qiyue Hu、Ted W. Johnson、Jon E. Kuehler、Atsuo Kuki、Hieu Lam、Wen Liu、Dawn Nowlin、Qinghai Peng、Sadayappan V. Rahavendran、Steven P. Tanis、Khanh T. Tran、Hai Wang、Anle Yang、Junhu Zhang

  DOI：10.1021/jm900862n

  日期：2009.11.26

  HIV-1 integrase (IN) is one of three enzymes encoded by the HIV genome and is essential for viral replication. Recently, HIV-1 IN inhibitors have emerged as a new promising class of therapeutics. Herein, we report the discovery of azaindole carboxylic acids and azaindole hydroxamic acids as potent inhibitors of the HIV-1 IN enzyme and their structure-activity relationships. Several 4-fluorobenzyl substituted azaindole hydroxamic acids showed potent antiviral activities in cell-based assays and offered a structurally simple scaffold for the development of novel HIV-1 IN inhibitors.