1-(4-甲氧基苯基)-2,5-二甲基-1H-吡咯-3-甲醛 | 347331-30-0

• 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-(4-甲氧基苯基)-2,5-二甲基-1H-吡咯-3-甲醛
• 英文名称: 1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrole-3-carbaldehyde
• 英文别名: 1-(4-methoxyphenyl)-2,5-dimethylpyrrole-3-carbaldehyde
• CAS: 347331-30-0
• 化学式: C₁₄H₁₅NO₂
• mdl: MFCD02614740
• 分子量: 229.279
• InChiKey: APTDNVFPUFIPJW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.214
• 拓扑面积：
  31.2
• 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：

  2,4-噻唑烷二酮 、 1-(4-甲氧基苯基)-2,5-二甲基-1H-吡咯-3-甲醛 在 哌啶 作用下， 以 甲苯 为溶剂， 反应 1.0h， 以63%的产率得到(Z)-5-[(1-(4-methoxyphenyl)-2,5-dimethyl-1H-pyrrol-3-yl)methylene]thiazolidine-2,4-dione
  参考文献：
  名称：

  具有激动剂/拮抗剂转换的新 FXR 配体化学型

  摘要：

  胆汁酸敏感转录因子法尼醇 X 受体 (FXR) 的治疗性调节是对抗肝脏和代谢疾病的一种有吸引力的策略。尽管有几种高效的 FXR 激动剂，但 FXR 调节剂的结构多样性是有限的，并且需要新的配体支架。在这里，我们报告了一种新的 FXR 调节剂化学型的结构-活性关系，其活性可以通过两个小的结构修饰在激动和拮抗之间进行调节。从弱 FXR/PPAR 激动剂开始，我们开发了具有纳摩尔到低微摩尔效力和结合亲和力的选择性 FXR 激活剂和拮抗剂。新的 FXR 配体化学型在天然细胞环境中调节 FXR 活性，具有良好的代谢稳定性，并且缺乏细胞毒性。

  DOI：

  10.1021/acsmedchemlett.0c00647
• 作为产物：
  描述：

  甲氧苯胺 在 对甲苯磺酸 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 反应 1.67h， 生成 1-(4-甲氧基苯基)-2,5-二甲基-1H-吡咯-3-甲醛
  参考文献：
  名称：

  易于合成的针对肺结核分枝杆菌的活体内具有显着活性的螺环化合物

  摘要：

  社会急需治疗结核病的新的有效药物。为了启动所需的领导才能运动，最近对制药公司的图书馆进行了起点评估。GlaxoSmithKline（GSK）库产生了许多高质量的匹配结果，并将相关数据置于公共领域，以激发更广泛社区的参与。此处描述了一个这样的系列，螺环化合物。这些化合物是通过传统的内部研究和开源方法相结合的方法进行探索的。该系列得益于特别简单的结构和较短的合成化学路线。该系列的许多成员均显示出惊人的效力和低毒性，并且其中一种类似物证实了在小鼠模型中具有高度前景的体内活性。

  DOI：

  10.1021/acs.jmedchem.8b01533

文献信息

• Synthesis, Structure and In Vitro Anti-Trypanosomal Activity of Non-Toxic Arylpyrrole-Based Chalcone Derivatives
  作者：Ayanda I. Zulu、Ogunyemi O. Oderinlo、Cuan Kruger、Michelle Isaacs、Heinrich C. Hoppe、Vincent J. Smith、Clinton G. L. Veale、Setshaba D. Khanye

  DOI：10.3390/molecules25071668

  日期：——

  With an intention of identifying chalcone derivatives exhibiting anti-protozoal activity, a cohort of relatively unexplored arylpyrrole-based chalcone derivatives were synthesized in moderate to good yields. The resultant compounds were evaluated in vitro for their potential activity against a cultured Trypanosoma brucei brucei 427 strain. Several compounds displayed mostly modest in vitro anti-trypanosomal activity with compounds 10e and 10h emerging as active candidates with IC50 values of 4.09 and 5.11 µM, respectively. More importantly, a concomitant assessment of their activity against a human cervix adenocarcinoma (HeLa) cell line revealed that these compounds are non-toxic.

  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。
• 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。
• Discovery and Structure–Activity Relationships of Pyrrolone Antimalarials
  作者：Dinakaran Murugesan、Alka Mital、Marcel Kaiser、David M. Shackleford、Julia Morizzi、Kasiram Katneni、Michael Campbell、Alan Hudson、Susan A. Charman、Clive Yeates、Ian H. Gilbert

  DOI：10.1021/jm400009c

  日期：2013.4.11

  In the pursuit of new antimalarial leads, a phenotypic screening of various commercially sourced compound libraries was undertaken by the World Health Organisation Programme for Research and Training in Tropical Diseases (WHO-TDR). We report here the detailed characterization of one of the hits from this process, TDR32750 (8a), which showed potent activity against Plasmodium falciparum K1 (EC50 similar to 9 nM), good selectivity (>2000-fold) compared to a mammalian cell line (L6), and significant activity against a rodent model of malaria when administered intraperitoneally. Structure-activity relationship studies have indicated ways in which the molecule could be optimized. This compound represents an exciting start point for a drug discovery program for the development of a novel antimalarial.
• Improving the Potency of <i>N</i>-Aryl-2,5-dimethylpyrroles against Multidrug-Resistant and Intracellular Mycobacteria
  作者：Meir Touitou、Fabrizio Manetti、Camila Maringolo Ribeiro、Fernando Rogerio Pavan、Nicolò Scalacci、Katarina Zrebna、Neelu Begum、Dorothy Semenya、Antima Gupta、Sanjib Bhakta、Timothy D. McHugh、Hanoch Senderowitz、Melina Kyriazi、Daniele Castagnolo

  DOI：10.1021/acsmedchemlett.9b00515

  日期：2020.5.14

  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.
• Design and development of pyrrole carbaldehyde: an effective pharmacophore for enoyl-ACP reductase
  作者：Shrinivas D. Joshi、Devendra Kumar、Uttam A. More、Kap Seung Yang、Tejraj M. Aminabhavi

  DOI：10.1007/s00044-016-1517-y

  日期：2016.4

  Enoyl-ACP reductase is the key enzyme involved in FAS-II synthesis of mycolic acid in bacterial cell wall and is a promising target for discovering new chemical entity. The designed pharmacophores are the possible better tools to combat mutation in enoyl-ACP enzyme, which leads to a decrease in volume of triclosan binding site. Compound 3a showed H-bonding interactions similar to that of triclosan with enoyl-ACP enzyme and with a better docking score (C score 8.81), while the compound 3f showed additional interaction with MET98.H amino acid residue. The 3D-QSAR computations also support the docking study to develop novel pyrrole-based derivatives.Molecular docking 3D-QSAR studies and synthesis of active analogs of pyrrole carbaldehyde as better receptor fit pharmacophore for enoyl-ACP reductase along with in vitro antitubercular activity.