1-(4-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛 | 119673-50-6

• 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-(4-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛
• 中文别名: 1-(4-氟苯)-2,5-二甲基-1H-吡咯-3-甲醛
• 英文名称: 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde
• 英文别名: 1-(4-fluorophenyl)-2,5-dimethylpyrrole-3-carbaldehyde
• CAS: 119673-50-6
• 化学式: C₁₃H₁₂FNO
• mdl: MFCD02629483
• 分子量: 217.243
• InChiKey: COLPZCHNJIVKMV-UHFFFAOYSA-N

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

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  1-(4-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛 以 四氢呋喃 、 溶剂黄146 为溶剂， 反应 36.0h， 生成 O-benzyl-N-((1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrol-3-yl)-methyl)hydroxylamine
  参考文献：
  名称：

  Design and Synthesis of 1-((1,5-Bis(4-chlorophenyl)-2-methyl-1H-pyrrol-3-yl)methyl)-4-methylpiperazine (BM212) and N-Adamantan-2-yl-N′-((E)-3,7-dimethylocta-2,6-dienyl)ethane-1,2-diamine (SQ109) Pyrrole Hybrid Derivatives: Discovery of Potent Antitubercular Agents Effective against Multidrug-Resistant Mycobacteria

  摘要：

  Novel pyrroles have been designed, synthesized, and evaluated against mycobacterial strains. The pyrroles have originally been designed as hybrids of the antitubercular drugs BM212 (1) and SQ109 (2), which showed common chemical features with very similar topological distribution. A perfect superposition of the structures of 1 and 2 revealed by computational studies suggested the introduction of bulky substituents at the terminal portion of the pyrrole C3 side chain and the removal of the CS aryl moiety. Five compounds showed high activity toward Mycobacterium tuberculosis, while 9b and 9c were highly active also against multidrug-resistant clinical isolates. Compound 9c showed low eukaryotic cell toxicity, turning out to be an excellent lead candidate for preclinical trials. In addition, four compounds showed potent inhibition (comparable to that of verapamil) toward the whole-cell drug efflux pump activity of mycobacteria, thus turning out to be promising multidrug-resistance-reversing agents.

  DOI：

  10.1021/acs.jmedchem.6b00031
• 作为产物：
  描述：

  4-氟苯胺 在 三氯氧磷 作用下， 以 neat (no solvent) 为溶剂， 反应 20.33h， 生成 1-(4-氟苯基)-2,5-二甲基-1H-吡咯-3-甲醛
  参考文献：
  名称：

  Synthesis, Structure and In Vitro Anti-Trypanosomal Activity of Non-Toxic Arylpyrrole-Based Chalcone Derivatives

  摘要：

  为了确定具有抗原虫活性的蒲公英素衍生物，合成了一系列相对未被探索的基于芳基吡咯烯的蒲公英素衍生物，产率在中等到良好之间。所得化合物在体外评估其对培养的布鲁氏锥虫427株的潜在活性。几种化合物显示出主要是适度的体外抗锥虫活性，其中化合物10e和10h 显示出活性，IC50值分别为4.09和5.11微摩尔。更重要的是，对它们在人宫颈腺癌（HeLa）细胞系中的活性进行同时评估表明这些化合物无毒。

  DOI：

  10.3390/molecules25071668

文献信息

• [EN] ANDROGEN RECEPTOR ANTAGONISTS<br/>[FR] ANTAGONISTES DU RÉCEPTEUR DES ANDROGÈNES
  申请人：ALPINE ANDROSCIENCES INC

  公开号：WO2019152731A1

  公开（公告）日：2019-08-08

  Compounds that inhibit the androgen receptor, pharmaceutical compositions comprising one or more of the compounds, as well as methods of treating cancer using such compounds are described.

  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。
• Efficient Synthesis and Anti-Tubercular Activity of a Series of Spirocycles: An Exercise in Open Science
  作者：Katrina A. Badiola、Diana H. Quan、James A. Triccas、Matthew H. Todd

  DOI：10.1371/journal.pone.0111782

  日期：——

  Tuberculosis afflicts an estimated 2 billion people worldwide and causes 1.3 million deaths annually. Chemotherapeutic solutions rely on drugs developed many years ago, with only one new therapeutic having been approved in the last 40 years. Given the rise of drug-resistant strains, there is an urgent need for the development of a more robust drug development pipeline. GlaxoSmithKline recently placed

  全世界估计有20亿人罹患结核病，每年造成130万人死亡。化学疗法解决方案依赖于多年前开发的药物，在过去的40年中仅批准了一种新的疗法。鉴于耐药菌株的增加，迫切需要开发更强大的药物开发渠道。GlaxoSmithKline最近将177条新颖的抗结核引线的结构和活性置于公共领域，以及对某些系列进行持续优化的结果。由于许多化合物源于筛选活动，因此其来源尚不清楚，在许多情况下未报告合成路线。在这里，我们介绍一种称为“螺旋”的GSK化合物家族的几种新型类似物的有效合成。-使用oxa-Pictet-Spengler反应。从药物化学的角度来看，这些新化合物具有吸引力，其中一些对强毒力菌株有效，这表明该类化合物值得进一步研究。该研究是使用开源方法进行的，为社区提供了实时访问所有原始实验数据的完全权限。
• 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。
• 基于阳离子自由基的基因递送系统的制备及其在胰腺癌治疗中的应用
  申请人：华南理工大学

  公开号：CN117603119A

  公开（公告）日：2024-02-27

  本发明公开了一种基于阳离子自由基的基因递送系统的制备及其在胰腺癌治疗中的应用。本发明合成了一系列吡咯化合物，其结构式如式I或式III所示；然后对这些化合物进行筛选，发现2,5‑二甲基‑1‑苯基‑1H‑吡咯衍生物在酸性环境下迅速转化为红‑近红外发射的吡咯自由基阳离子(P·+)，说明吡咯自由基分子具有优异的生物成像能力。本发明进一步将吡咯自由基阳离子P6·+作为线粒体靶向功能化基因载体，通过静电吸附的方式与KRAS siRNA结合，自组装形成P6@siKRAS双功能纳米颗粒，能够有效地诱导胰腺癌细胞中mutp53和致癌KRAS蛋白的同时降解，为胰腺癌提供了一种新的治疗策略。
• 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.