1-(4-chlorobenzyl)-2,5-dimethyl-1H-pyrrole | 342045-92-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-(4-chlorobenzyl)-2,5-dimethyl-1H-pyrrole
• 英文别名: 1-[(4-chlorophenyl)methyl]-2,5-dimethylpyrrole
• CAS: 342045-92-5
• 化学式: C₁₃H₁₄ClN
• mdl: MFCD01411867
• 分子量: 219.714
• InChiKey: LEVXUKJBTZXDGF-UHFFFAOYSA-N

物化性质

• 沸点：
  322.9±32.0 °C(Predicted)
• 密度：
  1.08±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  15
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  4.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  1-(4-chlorobenzyl)-2,5-dimethyl-1H-pyrrole 在 4-二甲氨基吡啶 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 16.0h， 生成 2-(1-(4-chlorobenzyl)-2,5-dimethyl-1H-pyrrol-3-yl)-2-oxo-N-(pyridin-4-yl)acetamide
  参考文献：
  名称：

  Indibulin 类似物的设计、合成和细胞毒性评估

  摘要：

  摘要 Indibulin 是最有效的微管蛋白聚合抑制剂之一，周围神经病变最小。设计和合成了新的 indibulin 类似物以研究它们的抗癌活性。目标化合物 4a-i 是在多步反应中合成的，从相关的吲哚衍生物开始。化合物 4f 对 HT-29 和 Caco-2 细胞系显示出最高的细胞毒活性，其各自的半数抑制浓度 (IC50) 值为 5.1 μm 和 7.3 μm。在 T47-D 细胞系的情况下，化合物 4c 发挥最佳细胞毒活性，IC50 值为 11.5 μm。在 HT-29 细胞的细胞周期分析中，5.1 μm 的化合物 4f 显示亚 G1 期的细胞百分比增加。共，合成了9个目标化合物，并通过红外光谱（IR）、质子核磁共振（1H NMR）、碳13核磁共振（13C NMR）、质谱（MS）和元素分析进行​​了表征。一些化合物对癌细胞系显示出良好的细胞毒活性。

  DOI：

  10.1515/hc-2018-0016
• 作为产物：
  描述：

  在 Aspergillus niger monoamine oxidase variant D₅ 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 1-(4-chlorobenzyl)-2,5-dimethyl-1H-pyrrole
  参考文献：
  名称：

  Unveiling the Biocatalytic Aromatizing Activity of Monoamine Oxidases MAO-N and 6-HDNO: Development of Chemoenzymatic Cascades for the Synthesis of Pyrroles

  摘要：

  A chemoenzymatic cascade process for the sustainable production of pyrroles has been developed. Pyrroles were synthesized by exploiting the previously unexplored aromatizing activity of monoamine oxidase enzymes (MAO-N and 6-HDNO). MAO-N/6-HDNO whole cell biocatalysts are able to convert 3-pyrrolines into pyrroles under mild conditions and in high yields. Moreover, MAO-N can work in combination with the ruthenium Grubbs catalyst, leading to the synthesis of pyrroles from diallylamines/-anilines in a one-pot cascade metathesis aromatization sequence.

  DOI：

  10.1021/acscatal.6b03081

文献信息

• Sustainable Manganese-Catalyzed Solvent-Free Synthesis of Pyrroles from 1,4-Diols and Primary Amines
  作者：Jannik C. Borghs、Yury Lebedev、Magnus Rueping、Osama El-Sepelgy

  DOI：10.1021/acs.orglett.8b03506

  日期：2019.1.4

  A general and selective metal-catalyzed conversion of biomass-derived primary diols and amines to the highly valuable 2,5-unsubstituted pyrroles has been developed. The reaction is catalyzed by a stable nonprecious manganese complex (1 mol %) in the absence of organic solvents whereby water and molecular hydrogen are the only side products. The manganese catalyst shows unprecedented selectivity, avoiding

  已经开发了一般的和选择性的金属催化的生物质衍生的伯二醇和胺到高度有价值的2，5-未取代的吡咯的转化。在没有有机溶剂的情况下，该反应由稳定的非贵金属锰配合物（1摩尔％）催化，其中水和分子氢是唯一的副产物。锰催化剂显示出前所未有的选择性，避免了吡咯烷，环状酰亚胺和内酯的形成。
• Novel and highly efficient preparation of pyrroles using supported ionic liquid ILCF3SO3@SiO2 as a heterogeneous catalyst
  作者：Yang Liu、Yu Lin Hu

  DOI：10.1007/s13738-018-1300-8

  日期：2018.5

  AbstractA supported ionic liquid ILCF3SO3@SiO2 was synthesized and used as a highly efficient catalyst in the Paal–Knorr reaction for the preparation of pyrroles. The heterogeneous catalyst could be easily recovered and recycled for five times without noticeable loss of catalytic activity. Also a possible reaction mechanism is provided. Graphical Abstract

  摘要合成了负载型离子液体ILCF 3 SO 3 @SiO 2，并在Paal-Knorr反应中用作制备吡咯的高效催化剂。该非均相催化剂可以容易地回收和再循环五次，而没有明显的催化活性损失。还提供了可能的反应机理。 图形概要
• Tapping into the antitubercular potential of 2,5-dimethylpyrroles: A structure-activity relationship interrogation
  作者：Dorothy Semenya、Meir Touitou、Domiziana Masci、Camila Maringolo Ribeiro、Fernando Rogerio Pavan、Guilherme Felipe Dos Santos Fernandes、Beatrice Gianibbi、Fabrizio Manetti、Daniele Castagnolo

  DOI：10.1016/j.ejmech.2022.114404

  日期：2022.7

  An exploration of the chemical space around a 2,5-dimethylpyrrole scaffold of antitubercular hit compound 1 has led to the identification of new derivatives active against Mycobacterium tuberculosis and multidrug-resistant clinical isolates. Analogues incorporating a cyclohexanemethyl group on the methyleneamine side chain at C3 of the pyrrole core, including 5n and 5q, exhibited potent inhibitory

  对抗结核打击化合物1的 2,5-二甲基吡咯支架周围化学空间的探索导致鉴定出对结核分枝杆菌和耐多药临床分离株具有活性的新衍生物。在吡咯核心 C3 的亚甲基胺侧链上加入环己烷甲基的类似物，包括5n和5q ，对结核分枝杆菌表现出有效的抑制作用菌株，证实了该部分对其抗分枝杆菌活性的重要性。此外，选定的衍生物对人肺成纤维细胞和/或鼠巨噬细胞显示出有希望的细胞毒性特征，证明可有效抑制细胞内分枝杆菌的生长，并引起杀菌作用或与1相当的抑菌活性。计算研究表明，新化合物与推定的靶标 MmpL3 的结合方式与已知抑制剂 BM212 和 SQ109 的结合方式相似。
• Copper/Nitroxyl-Catalyzed Synthesis of Pyrroles by Oxidative Coupling of Diols and Primary Amines at Room Temperature
  作者：Weiru Fu、Lina Zhu、Shangzhi Tan、Zhengjia Zhao、Xiangzhu Yu、Lianyue Wang

  DOI：10.1021/acs.joc.2c01646

  日期：2022.10.7

  The Cu/ABNO-catalyzed aerobic oxidative coupling of diols and primary amines to access N-substituted pyrroles is highlighted (ABNO = 9-azabicyclo[3.3.1]nonane N-oxyl). The reaction proceeds at room temperature with an O2 balloon as the oxidant using commercially available materials as the substrates and catalysts. The catalyst system is characterized by a broad range of substrates and a good tolerance

  突出显示了 Cu/ABNO 催化的二醇和伯胺的需氧氧化偶联以获得 N 取代的吡咯（ABNO = 9-氮杂双环 [3.3.1] 壬烷N-氧基）。反应在室温下以 O 2气球作为氧化剂进行，使用市售材料作为底物和催化剂。该催化剂体系的特点是广泛的底物和对敏感官能团的良好耐受性。克级实验证明了该系统的实用性。
• 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.