1-(3-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛 | 428497-01-2

• 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-(3-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛
• 英文名称: 1-(3-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde
• 英文别名: 1-(3-fluorophenyl)-2,5-dimethylpyrrole-3-carbaldehyde
• CAS: 428497-01-2
• 化学式: C₁₃H₁₂FNO
• mdl: MFCD02611660
• 分子量: 217.243
• InChiKey: PLCBYAIRHPWRPH-UHFFFAOYSA-N

物化性质

• 沸点：
  345.7±42.0 °C(Predicted)
• 密度：
  1.11±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.153
• 拓扑面积：
  22
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-甲基-2-甲基亚氨基-1,3-噻唑烷-4-酮 、 1-(3-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛 在 哌啶 作用下， 以 乙醇 为溶剂， 反应 4.0h， 生成 5-[[1-(3-fluorophenyl)-2,5-dimethylpyrrol-3-yl]methylidene]-3-methyl-2-methylimino-1,3-thiazolidin-4-one
  参考文献：
  名称：

  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

  摘要：

  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.

  DOI：

  10.1016/j.bmcl.2011.09.049
• 作为产物：
  描述：

  2,5-己二酮 在 草酰氯 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.25h， 生成 1-(3-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛
  参考文献：
  名称：

  吡咯-噻唑烷酮杂化物作为一种新结构的广谱抗感染药

  摘要：

  设计、合成了一系列吡咯-噻唑烷酮杂化物，并评估其针对 ESKAP 细菌组和分枝杆菌病原体的活性。在该系列中，化合物9d显示出显着的抗金黄色葡萄球菌活性。金黄色葡萄球菌(MIC = 0.5 μg/mL) 和化合物9k显示出最有希望的抗金黄色葡萄球菌活性。结核病H37Rv（MIC = 0.5 μg/mL）。当针对 Vero 细胞进行测试时，发现有效的衍生物是无毒的。化合物9d在针对几种MRSA和VRSA菌株的体外评估中产生了与标准药物相当或更好的活性。在抗生物膜测定中， 9d减少了S。在 10 倍 MIC 时，金黄色葡萄球菌生物膜增加 >11%。吡咯-噻唑烷酮杂化物表现出的双重抑制作用证实了它们作为新型有前途的抗感染剂的潜力。

  DOI：

  10.1016/j.ejmech.2023.115757

文献信息

• 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.
• Pyrrole-thiazolidinone hybrids as a new structural class of broad-spectrum anti-infectives
  作者：Shujauddin Ahmed、Alka Mital、Abdul Akhir、Deepanshi Saxena、Mohammad Naiyaz Ahmad、Arunava Dasgupta、Sidharth Chopra、Rahul Jain

  DOI：10.1016/j.ejmech.2023.115757

  日期：2023.11

  pyrrole-thiazolidinone hybrids was designed, synthesized and evaluated for activities against ESKAP bacteria panel and mycobacterial pathogens. From the series, compound 9d showed prominent activity against S. aureus (MIC = 0.5 μg/mL) and compound 9k showed the most promising activity against M. tuberculosis H37Rv (MIC = 0.5 μg/mL). Potent derivatives were found to be non-toxic when tested against Vero cells.

  设计、合成了一系列吡咯-噻唑烷酮杂化物，并评估其针对 ESKAP 细菌组和分枝杆菌病原体的活性。在该系列中，化合物9d显示出显着的抗金黄色葡萄球菌活性。金黄色葡萄球菌(MIC = 0.5 μg/mL) 和化合物9k显示出最有希望的抗金黄色葡萄球菌活性。结核病H37Rv（MIC = 0.5 μg/mL）。当针对 Vero 细胞进行测试时，发现有效的衍生物是无毒的。化合物9d在针对几种MRSA和VRSA菌株的体外评估中产生了与标准药物相当或更好的活性。在抗生物膜测定中， 9d减少了S。在 10 倍 MIC 时，金黄色葡萄球菌生物膜增加 >11%。吡咯-噻唑烷酮杂化物表现出的双重抑制作用证实了它们作为新型有前途的抗感染剂的潜力。