4-[3-(叠氮基甲基)苯基]-2-羟基-4-氧代-2-丁烯酸 | 544467-07-4

• 物质功能分类: 生物化工 - 抑制剂 - 微生物学(Microbiology)
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 4-[3-(叠氮基甲基)苯基]-2-羟基-4-氧代-2-丁烯酸
• 英文名称: NIH 118-D-24
• 英文别名: 4-(3-Azidomethyl-phenyl)-2,4-dioxo-butyric acid；4-[3-(azidomethyl)phenyl]-2,4-dioxobutanoic acid
• CAS: 544467-07-4
• 化学式: C₁₁H₉N₃O₄
• 分子量: 247.21
• InChiKey: MXECCJRSXQRLTO-UHFFFAOYSA-N

物化性质

• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  18
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  85.8
• 氢给体数：
  1
• 氢受体数：
  6

制备方法与用途

生物活性

HIV-1整合酶抑制剂可用于抗HIV。

反应信息

• 作为产物：
  描述：

  1-(3-(溴甲基)苯基)乙酮 在 sodium hydroxide 、 sodium azide 、 sodium hydride 作用下， 以 1,4-二氧六环 、 水 、 丙酮 、 甲苯 为溶剂， 反应 1.0h， 生成 4-[3-(叠氮基甲基)苯基]-2-羟基-4-氧代-2-丁烯酸
  参考文献：
  名称：

  Azido-Containing aryl β-Diketo acid HIV-1 integrase inhibitors

  摘要：

  Aryl beta-diketo acids (ADK) comprise a general class of potent HIV-1 integrase (IN) inhibitors, which can exhibit selective inhibition of strand transfer reactions in extracellular recombinant IN assays and provide potent antiviral effects in HIV-infected cells. Recent studies have shown that polycyclic aryl or aryl rings bearing aryl-containing substituents are components of potent members of this class. Reported herein is the first use of azido functionality as an aryl replacement in beta-diketo acid IN inhibitors. The ability of azido-containing inhibitors to exhibit potent inhibition of IN and antiviral protection in HIV-infected cells, renders the azide group of potential value in the further development of ADK-based IN inhibitors. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(03)00059-3

文献信息

• Azido-Containing aryl β-Diketo acid HIV-1 integrase inhibitors
  作者：Xuechun Zhang、Godwin C.G Pais、Evguenia S Svarovskaia、Christophe Marchand、Allison A Johnson、Rajeshri G Karki、Marc C Nicklaus、Vinay K Pathak、Yves Pommier、Terrence R Burke

  DOI：10.1016/s0960-894x(03)00059-3

  日期：2003.3

  Aryl beta-diketo acids (ADK) comprise a general class of potent HIV-1 integrase (IN) inhibitors, which can exhibit selective inhibition of strand transfer reactions in extracellular recombinant IN assays and provide potent antiviral effects in HIV-infected cells. Recent studies have shown that polycyclic aryl or aryl rings bearing aryl-containing substituents are components of potent members of this class. Reported herein is the first use of azido functionality as an aryl replacement in beta-diketo acid IN inhibitors. The ability of azido-containing inhibitors to exhibit potent inhibition of IN and antiviral protection in HIV-infected cells, renders the azide group of potential value in the further development of ADK-based IN inhibitors. (C) 2003 Elsevier Science Ltd. All rights reserved.