1-[(4-硝基苯基)甲基]吡咯-2-甲醛 | 107484-34-4

• 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-[(4-硝基苯基)甲基]吡咯-2-甲醛
• 英文名称: 1-(4-nitrobenzil)pirrol-2-carbossaldeide
• 英文别名: 1H-Pyrrole-2-carboxaldehyde, 1-[(4-nitrophenyl)methyl]-；1-[(4-nitrophenyl)methyl]pyrrole-2-carbaldehyde
• CAS: 107484-34-4
• 化学式: C₁₂H₁₀N₂O₃
• mdl: MFCD11909528
• 分子量: 230.223
• InChiKey: WRYZZFHVGAKORA-UHFFFAOYSA-N

物化性质

• 沸点：
  415.3±25.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  67.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-[(4-硝基苯基)甲基]吡咯-2-甲醛 在 sodium hydroxide 、 sodium ethanolate 作用下， 以 四氢呋喃 为溶剂， 反应 25.75h， 生成 (E)-6-[1-(4-Nitro-benzyl)-1H-pyrrol-2-yl]-2,4-dioxo-hex-5-enoic acid ethyl ester
  参考文献：
  名称：

  Design, synthesis and biological evaluation of heteroaryl diketohexenoic and diketobutanoic acids as HIV-1 integrase inhibitors endowed with antiretroviral activity

  摘要：

  Highly active anti-retroviral therapy (HAART) using reverse transcriptase (RT) and protease (PR) inhibitors and, more recently, inhibitors of the fusion is currently the best clinical approach in combating acquired immunodeficiency syndrome (AIDS), caused by infection from human immunodeficiency virus type 1 (HIV-1). However, this therapy does not completely eradicate the virus, so that resistant strains easily emerge. The above problem calls urgently for research on inhibitors of further viral targets such as integrase (IN), the third enzyme produced by HIV. Recently, our research group was engaged in studies on conformationally restrained cinnamoyl compounds related to curcumin as anti-IN agents. Compounds containing both a 3,4,5-trihydroxyphenyl group and a carboxylic acid function were potent IN inhibitors active against viral replication. More recently, a promising new class of inhibitors synthesized by Merck Company has emerged, which contain aryldiketoacid (ADK) functionality. The ADKs selectively inhibited the stand transfer (ST) step of integration and were proven to be effective IN inhibitors in vivo. Our interest in the field of IN inhibitors led us to design pyrrole and indole derivatives containing both a cinnamoyl moiety and a diketoacid group. A number of the cited derivatives were proven potent IN inhibitors, which selectively inhibited the ST step at submicromolar concentrations and were effective against virus replication in HIV-1 infected cells.

  DOI：

  10.1016/j.farmac.2005.03.008
• 作为产物：
  描述：

  2-吡咯甲醛 、 1-(氯甲基)-4-硝基苯 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 1-[(4-硝基苯基)甲基]吡咯-2-甲醛
  参考文献：
  名称：

  6-Aryl-2,4-dioxo-5-hexenoic acids, novel integrase inhibitors active against HIV-1 multiplication in cell-based assays

  摘要：

  A series of 6-aryl-2,4-dioxo-5-hexenoic acids, were synthesized and tested against HIV-1 in cell-based assays and against recombinant HIV-1 integrase (rIN) in enzyme assays. Compound 8a showed potent antiretroviral activity (EC50 = 1.5 muM) and significant inhibition against rIN (strand transfer: IC50 = 7.9 muM; 3'-processing: IC50 = 7.0 muM). A preliminary molecular modeling study was carried out to compare the spatial conformation of 8a with those of L-731,988 (4) and 5CITEP (7) in the IN core. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.01.037

文献信息

• One-Pot Amberlyst 15-Controlled Cyclocondensation of Piperidines and Arylaldehydes: Synthesis of 3,5-Diarylmethylpyridines
  作者：Meng-Yang Chang、Yu-Lin Tsai

  DOI：10.1021/acs.joc.9b03315

  日期：2020.4.17

  Amberlyst 15-controlled one-pot easy-operational intermolecular cyclocondensation of substituted piperidines with arylaldehydes provides diversified 3,5-diarylmethylpyridines in high to excellent yields under refluxing toluene conditions. The uses of various acidic solid supports and reaction solvents are investigated for facile and efficient transformation. A plausible mechanism has been proposed

  在芳基醛回流下，Amberlyst 15受控的一锅式易操作的哌啶与芳醛的分子间环缩合反应提供了多样化的3,5-二芳基甲基吡啶。研究了各种酸性固体载体和反应溶剂的使用，以实现简便高效的转化。已经提出了一种合理的机制。
• Stefancich; Corelli; Massa, Farmaco, Edizione Scientifica, 1987, vol. 42, # 1, p. 3 - 16
  作者：Stefancich、Corelli、Massa、Silvestri、Panico、Artico、Simonetti

  DOI：——

  日期：——
• Design, synthesis and biological evaluation of heteroaryl diketohexenoic and diketobutanoic acids as HIV-1 integrase inhibitors endowed with antiretroviral activity
  作者：R. Di Santo、R. Costi、M. Artico、R. Ragno、G. Greco、E. Novellino、C. Marchand、Y. Pommier

  DOI：10.1016/j.farmac.2005.03.008

  日期：2005.5

  Highly active anti-retroviral therapy (HAART) using reverse transcriptase (RT) and protease (PR) inhibitors and, more recently, inhibitors of the fusion is currently the best clinical approach in combating acquired immunodeficiency syndrome (AIDS), caused by infection from human immunodeficiency virus type 1 (HIV-1). However, this therapy does not completely eradicate the virus, so that resistant strains easily emerge. The above problem calls urgently for research on inhibitors of further viral targets such as integrase (IN), the third enzyme produced by HIV. Recently, our research group was engaged in studies on conformationally restrained cinnamoyl compounds related to curcumin as anti-IN agents. Compounds containing both a 3,4,5-trihydroxyphenyl group and a carboxylic acid function were potent IN inhibitors active against viral replication. More recently, a promising new class of inhibitors synthesized by Merck Company has emerged, which contain aryldiketoacid (ADK) functionality. The ADKs selectively inhibited the stand transfer (ST) step of integration and were proven to be effective IN inhibitors in vivo. Our interest in the field of IN inhibitors led us to design pyrrole and indole derivatives containing both a cinnamoyl moiety and a diketoacid group. A number of the cited derivatives were proven potent IN inhibitors, which selectively inhibited the ST step at submicromolar concentrations and were effective against virus replication in HIV-1 infected cells.
• 6-Aryl-2,4-dioxo-5-hexenoic acids, novel integrase inhibitors active against HIV-1 multiplication in cell-based assays
  作者：Roberta Costi、Roberto Di Santo、Marino Artico、Alessandra Roux、Rino Ragno、Silvio Massa、Enzo Tramontano、Massimiliano La Colla、Roberta Loddo、M.Elena Marongiu、Alessandra Pani、Paolo La Colla

  DOI：10.1016/j.bmcl.2004.01.037

  日期：2004.4

  A series of 6-aryl-2,4-dioxo-5-hexenoic acids, were synthesized and tested against HIV-1 in cell-based assays and against recombinant HIV-1 integrase (rIN) in enzyme assays. Compound 8a showed potent antiretroviral activity (EC50 = 1.5 muM) and significant inhibition against rIN (strand transfer: IC50 = 7.9 muM; 3'-processing: IC50 = 7.0 muM). A preliminary molecular modeling study was carried out to compare the spatial conformation of 8a with those of L-731,988 (4) and 5CITEP (7) in the IN core. (C) 2004 Elsevier Ltd. All rights reserved.