1-(2-氟苯基)-1H-吡咯-3-甲醛 | 691862-62-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 中文名称: 1-(2-氟苯基)-1H-吡咯-3-甲醛
• 英文名称: 1-(2-Fluoro-phenyl)-1H-pyrrole-3-carbaldehyde
• 英文别名: 1-(2-fluorophenyl)-1H-pyrrole-3-carbaldehyde；1-(2-fluorophenyl)pyrrole-3-carbaldehyde
• CAS: 691862-62-1
• 化学式: C₁₁H₈FNO
• mdl: MFCD05256430
• 分子量: 189.189
• InChiKey: YLNZOYYQKGBXTC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-(2-氟苯基)-1H-吡咯-3-甲醛 在 sodium hydroxide 、 silver nitrate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 1-(2-fluorophenyl)pyrrole-3-carboxylic acid
  参考文献：
  名称：

  Synthesis and in vitro antimycobacterial activity of novel 3-(1H-pyrrol-1-yl)-2-oxazolidinone analogues of PNU-100480

  摘要：

  Pursuing our search program for new antitubercular drugs we decided to explore the potentiality of oxazolidinone moiety by synthesizing novel 3-(1H-pyrrol-1-yl)-2-oxazolidinone analogues of PNU-100480. The new derivatives were tested against atypical mycobacteria as well as against drug resistant Mycobacterium tuberculosis and some of them exhibited a fairly good activity against Mycobacterium avium complex (MAC). (C) 2004 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2004.01.010
• 作为产物：
  描述：

  2-氟苯胺 在 草酰氯 、 溶剂黄146 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.5h， 生成 1-(2-氟苯基)-1H-吡咯-3-甲醛
  参考文献：
  名称：

  缩聚杂环。七、分子内芳香亲核置换法合成吡咯并[1,2-a]喹喔啉衍生物

  摘要：

  摘要 4-(4-Methyl-1-piperazinyl)-7-trifluoromethylpyrrolo[1,2-a]quinoxaline (CGS 12066B) 和相关类似物通过一个反应序列以良好的总收率制备，包括作为关键步骤的分子内取代芳族氟化物或硝基由羧酰胺部分组成。

  DOI：

  10.1080/00397919108021054

文献信息

• Synthesis, Anti-Inflammatory Activity, and in Vitro Antitumor Effect of a Novel Class of Cyclooxygenase Inhibitors: 4-(Aryloyl)phenyl Methyl Sulfones
  作者：Youssef Harrak、Giovanni Casula、Joan Basset、Glòria Rosell、Salvatore Plescia、Demetrio Raffa、Maria Grazia Cusimano、Ramon Pouplana、Maria Dolors Pujol

  DOI：10.1021/jm100398z

  日期：2010.9.23

  Following our previous research on anti-inflammatory drugs (NSAIDs), we report on the design and synthesis of 4-(aryloyl)phenyl methyl sulfones. These substances were characterized for their capacity to inhibit cyclooxygenase (COX-1 and COX-2) isoenzymes. Molecular modeling studies showed that the methylsulfone group of these compounds was inserted deep in the pocket of the human COX-2 binding site

  在我们先前对消炎药（NSAIDs）的研究之后，我们报告了4-（芳酰基）苯基甲基砜的设计和合成。这些物质的特征在于它们具有抑制环氧合酶（COX-1和COX-2）同工酶的能力。分子模型研究表明，这些化合物的甲基砜基团以无法阻止氢与Arg120，Ser353和Tyr355通过氧原子键合的方向插入人COX-2结合位点的口袋深处。所述Ñ -arylindole 33是COX-2的最有效的抑制剂，也是最选择性（COX-1 / COX-2的IC 50之比为262）。吲哚衍生物33进一步在体内测试了其在大鼠中的抗炎活性。该化合物显示出比布洛芬更大的抑制活性。其它化合物（20，26，9，和30）显示出对角叉菜胶诱导的炎症活性强。后一种化合物在体外抑制人细胞株K562，NCI-H460和HT-29增殖的能力较弱。
• Discovery, synthesis and SAR analysis of novel selective small molecule S1P4-R agonists based on a (2Z,5Z)-5-((pyrrol-3-yl)methylene)-3-alkyl-2-(alkylimino)thiazolidin-4-one chemotype
  作者：Mariangela Urbano、Miguel Guerrero、Subash Velaparthi、Melissa Crisp、Peter Chase、Peter Hodder、Marie-Therese Schaeffer、Steven Brown、Hugh Rosen、Edward Roberts

  DOI：10.1016/j.bmcl.2011.09.049

  日期：2011.11

  High affinity and selective S1P(4) receptor (S1P(4)-R) small molecule agonists may be important proof-of-principle tools used to clarify the receptor biological function and effects to assess the therapeutic potential of the S1P4-R in diverse disease areas including treatment of viral infections and thrombocytopenia. A high-throughput screening campaign of the Molecular Libraries-Small Molecule Repository was carried out by our laboratories and identified (2Z,5Z)-5-((1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene)-3-methyl-2-(methylimino) thiazolidin-4-one as a promising S1P(4)-R agonist hit distinct from literature S1P(4)-R modulators. Rational chemical modifications of the hit allowed the identification of a promising lead molecule with low nanomolar S1P(4)-R agonist activity and exquisite selectivity over the other S1P(1-3,5)-Rs family members. The lead molecule herein disclosed constitutes a valuable pharmacological tool to explore the effects of the S1P(4)-R signaling cascade and elucidate the molecular basis of the receptor function. (C) 2011 Elsevier Ltd. All rights reserved.
• Novel HIV-1 protease inhibitors active against multiple PI-Resistant viral strains: coadministration with indinavir
  作者：Nancy J. Kevin、Joseph L. Duffy、Brian A. Kirk、Kevin T. Chapman、William A. Schleif、David B. Olsen、Mark Stahlhut、Carrie A. Rutkowski、Lawrence C. Kuo、Lixia Jin、Jiunn H. Lin、Emilio A. Emini、James R. Tata

  DOI：10.1016/j.bmcl.2003.08.049

  日期：2003.11

  HIV-1 protease inhibitors (PI) with an N-arylpyrrole moiety in the P-3 position afforded excellent antiviral potency and substantially improved aqueous solubility over previously reported variants. The rapid in vitro clearance of these compounds in human liver microsomes prompted oral coadministration with indinavir to hinder their metabolism by the cyctochrome P450 3A4 isozyme and allow for in vivo PK assessment. (C) 2003 Elsevier Ltd. All rights reserved.
• Polycondensed Heterocycles. VII. A Convenient Synthesis of Pyrrolo[1,2-a]quinoxaline Derivatives by Intramolecular Aromatic Nucleophilic Displacement
  作者：G. Campiani、V. Nacci、F. Corelli、M. Anzini

  DOI：10.1080/00397919108021054

  日期：1991.8

  Abstract 4-(4-Methyl-1-piperazinyl)-7-trifluoromethylpyrrolo[1,2-a]quinoxaline (CGS 12066B) and related analogs were prepared in good overall yield through a reaction sequence involving as a key step the intramolecular substitution of aromatic fluoride or nitro groups by a carboxamide moiety.

  摘要 4-(4-Methyl-1-piperazinyl)-7-trifluoromethylpyrrolo[1,2-a]quinoxaline (CGS 12066B) 和相关类似物通过一个反应序列以良好的总收率制备，包括作为关键步骤的分子内取代芳族氟化物或硝基由羧酰胺部分组成。
• Synthesis and in vitro antimycobacterial activity of novel 3-(1H-pyrrol-1-yl)-2-oxazolidinone analogues of PNU-100480
  作者：Gianluca Sbardella、Antonello Mai、Marino Artico、Roberta Loddo、Maria Grazia Setzu、Paolo La Colla

  DOI：10.1016/j.bmcl.2004.01.010

  日期：2004.3

  Pursuing our search program for new antitubercular drugs we decided to explore the potentiality of oxazolidinone moiety by synthesizing novel 3-(1H-pyrrol-1-yl)-2-oxazolidinone analogues of PNU-100480. The new derivatives were tested against atypical mycobacteria as well as against drug resistant Mycobacterium tuberculosis and some of them exhibited a fairly good activity against Mycobacterium avium complex (MAC). (C) 2004 Published by Elsevier Ltd.