1-(1H-咪唑-1-基)-2-(3-硝基苯基)乙酮 | 221121-32-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(1H-咪唑-1-基)-2-(3-硝基苯基)乙酮
• 英文名称: 1-Imidazol-1-yl-2-(3-nitro-phenyl)-ethanone
• 英文别名: 1-Imidazol-1-yl-2-(3-nitrophenyl)ethanone
• CAS: 221121-32-0
• 化学式: C₁₁H₉N₃O₃
• 分子量: 231.211
• InChiKey: ALMCDNOXZISQGR-UHFFFAOYSA-N

物化性质

• 沸点：
  463.5±47.0 °C(Predicted)
• 密度：
  1.35±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  80.7
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(1H-咪唑-1-基)-2-(3-硝基苯基)乙酮 在 肼 作用下， 以 四氢呋喃 为溶剂， 生成 2-(3-nitrophenyl)acetic hydrazide
  参考文献：
  名称：

  1,2,4-三唑类化合物作为A（2A）受体拮抗剂的合成与合成孔径雷达评估。

  摘要：

  报道了一系列三唑类化合物作为A（2A）受体拮抗剂的合成及其体外构效关系（SAR）。这导致鉴定出有效的，选择性的和可渗透的1,2,4-三唑，例如42种，以进一步在体内进行优化和评估。

  DOI：

  10.1016/j.bmcl.2003.09.095
• 作为产物：
  描述：

  3-硝基苯乙酸 、 N,N'-羰基二咪唑 以 四氢呋喃 为溶剂， 生成 1-(1H-咪唑-1-基)-2-(3-硝基苯基)乙酮
  参考文献：
  名称：

  1,2,4-三唑类化合物作为A（2A）受体拮抗剂的合成与合成孔径雷达评估。

  摘要：

  报道了一系列三唑类化合物作为A（2A）受体拮抗剂的合成及其体外构效关系（SAR）。这导致鉴定出有效的，选择性的和可渗透的1,2,4-三唑，例如42种，以进一步在体内进行优化和评估。

  DOI：

  10.1016/j.bmcl.2003.09.095

文献信息

• Kinetic and Thermodynamic Acidities of Substituted 1-Benzyl-1-methoxy-2-nitroethylenes. Strong Reduction of the Transition State Imbalance Compared to Other Nitroalkanes
  作者：Claude F. Bernasconi、Mahammad Ali、Janette C. Gunter

  DOI：10.1021/ja0211398

  日期：2003.1.1

  Acidity constants of six substituted 1-benzyl-1-methoxy-2-nitroethylenes (2-Z with Z = m-NO(2), m-CF(3), m-Cl, H, p-Me, p-MeO) and their respective nitronic acids were determined in 50% DMSO-50% water (v/v) at 20 degrees C. Kinetic data were obtained on the reversible deprotonation of all six 2-Z by OH(-) and piperidine and on the reversible deprotonation of 2-NO(2)() by piperazine, 1-(2-hydroxyethyl)piperazine

  六个取代的 1-苄基-1-甲氧基-2-硝基乙烯（2-Z 与 Z = m-NO(2)、m-CF(3)、m-Cl、H、p-Me、p-MeO）的酸度常数) 及其各自的硝基酸在 20 摄氏度的 50% DMSO-50% 水 (v/v) 中测定。获得了所有六个 2-Z 由 OH(-) 和哌啶可逆去质子化的动力学数据，以及哌嗪、1-（2-羟乙基）哌嗪和吗啉在同一溶剂中对 2-NO(2)() 进行可逆去质子化。这些数据可以确定 Brønsted 系数 alpha（取决于 2-Z 的酸度）和 beta（取决于胺碱度）。α > β 的事实表明存在过渡态不平衡，然而，这比芳基硝基甲烷的去质子化要小得多。
• 5-Alkyl-2-(alkylthio)-6-(2,6-dihalophenylmethyl)-3,4-dihydropyrimidin-4(3<i>H</i>)-ones:  Novel Potent and Selective Dihydro-alkoxy-benzyl-oxopyrimidine Derivatives
  作者：Antonello Mai、Marino Artico、Gianluca Sbardella、Silvio Massa、Ettore Novellino、Giovanni Greco、Anna Giulia Loi、Enzo Tramontano、Maria Elena Marongiu、Paolo La Colla

  DOI：10.1021/jm980260f

  日期：1999.2.1

  Molecular modeling analysis of compounds belonging to the recently published series of dihydroalkoxy-benzyl-oxopyrimidines (DABOs), such as S-DABOs and DATNOs, gave support to the design of new 2,6-disubstituted benzyl-DABO derivatives as highly potent and specific inhibitors of the HIV-1 reverse transcriptase (RT). To follow up on the novel DABO derivatives, we decided to investigate the effect of electron-withdrawing substituents in the benzyl unit of the S-DABO skeleton versus their anti-HIV-1 activity. Such chemical modifications impacted the inhibitory activity, especially when two halogen units were introduced at positions 2 and 6 in the phenyl portion of the benzyl group bound to C-6 of the pyrimidine ring. Various 5-alkyl-2-(alkyl(or cycloalkyl)thio)-6-(2,B-dichloro(or 2, 6-difluoro)phenylmethyl)-3,4-dihydropyrimidin-4(3H)-ones were then synthesized and tested as anti-HIV-1 agents in both cell-based and enzyme (recombinant reverse transcriptase, rRT) assays. Among the various mono- and disubstituted phenyl derivatives, the most potent were those containing a 6-(2,6-difluorophenylmethyl) substituent (F-DABOs), which showed EC50's ranging between 40 and 90 nM and selectivity indexes up to greater than or equal to 5000. An excellent correlation was found between EC50 and IC50 values which confirmed that these compounds act as inhibitors of the HIV-1 RT. The structure-activity relationships of the newly synthesized pyrimidinones are presented herein.