1-(2-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛 | 153881-54-0

• 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)-2,5-二甲基-1H-吡咯-3-甲醛
• 中文别名: 1-(2-氟苯基)-2,5-二甲基甲醛
• 英文名称: 1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxaldehyde
• 英文别名: 1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde；1-(2-fluorophenyl)-2,5-dimethylpyrrole-3-carbaldehyde
• CAS: 153881-54-0
• 化学式: C₁₃H₁₂FNO
• mdl: MFCD02611665
• 分子量: 217.243
• InChiKey: AWMIXYYZKHFFFW-UHFFFAOYSA-N

物化性质

• 沸点：
  343.4±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：

  2-甲基苯并唑 、 1-(2-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 3.5h， 以16%的产率得到(E)-2-(2-(1-(2-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)vinyl)benzo[d]oxazole
  参考文献：
  名称：

  [EN] ANDROGEN RECEPTOR ANTAGONISTS
  [FR] ANTAGONISTES DU RÉCEPTEUR DES ANDROGÈNES

  摘要：

  描述了抑制雄激素受体的化合物、包含一种或多种这些化合物的药物组合物，以及使用这些化合物治疗癌症的方法。

  公开号：

  WO2019152731A1
• 作为产物：
  描述：

  2,5-己二酮 在 对甲苯磺酸 、 三氯氧磷 作用下， 生成 1-(2-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛
  参考文献：
  名称：

  Improving the Potency of N-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria

  摘要：

  A series of N-phenyl-2,5-dimethylpyrrole derivatives, designed as hybrids of the antitubercular agents BM212 and SQ109, have been synthesized and evaluated against susceptible and drug-resistant mycobacteria strains. Compound 5d, bearing a cyclohexylmethylene side chain, showed high potency against M. tuberculosis including MDR-TB strains at submicromolar concentrations. The new compound shows bacteriostatic activity and low toxicity and proved to be effective against intracellular mycobacteria too, showing an activity profile similar to isoniazid.

  DOI：

  10.1021/acsmedchemlett.9b00515

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.