methyl 1-benzyl-2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate | 1320232-56-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯
• 英文名称: methyl 1-benzyl-2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate
• 英文别名: Methyl 1-benzyl-2,5-dimethyl-4-phenylpyrrole-3-carboxylate
• CAS: 1320232-56-1
• 化学式: C₂₁H₂₁NO₂
• 分子量: 319.403
• InChiKey: IMCAVVBMLNWDHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  31.2
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2,5-二氯吡咯-3-羧酸甲酯 在 四(三苯基膦)钯 、 pyridinium hydrobromide perbromide 、 sodium hydride 、 sodium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 、 水 、 mineral oil 为溶剂， 反应 7.0h， 生成 methyl 1-benzyl-2,5-dimethyl-4-phenyl-1H-pyrrole-3-carboxylate
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of 4-phenylpyrrole derivatives as novel androgen receptor antagonists

  摘要：

  A series of 4-phenylpyrrole derivatives D were designed, synthesized, and evaluated for their potential as novel orally available androgen receptor antagonists therapeutically effective against castration-resistant prostate cancers. 4-Phenylpyrrole compound 1 exhibited androgen receptor (AR) antagonistic activity against T877A and W741C mutant-type ARs as well as wild-type AR. An arylmethyl group incorporated into compound 1 contributed to enhancement of antagonistic activity. Compound 4n, 1-{[6-chloro-5-(hydroxymethyl)pyridin-3-yl]methyl}-4-(4-cyanophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonitrile exhibited inhibitory effects on tumor cell growth against the bicalutamide-resistant LNCaP-cxD2 cell line as well as the androgen receptor-dependent JDCaP cell line in a mouse xenograft model. These results demonstrate that this series of pyrrole compounds are novel androgen receptor antagonists with efficacy against prostate cancer cells, including castration-resistant prostate cancers such as bicalutamide-resistant prostate cancer. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.10.067

文献信息

• A facile and efficient synthesis of multisubstituted pyrroles from enaminoesters and nitroolefins
  作者：Zheng-Hui Guan、Liang Li、Zhi-Hui Ren、Jianli Li、Mi-Na Zhao

  DOI：10.1039/c1gc15278e

  日期：——

  A facile and efficient method for the synthesis of substituted pyrroles from enaminoesters and nitroolefins is reported. This general procedure provides a wide variety of multisubstituted pyrroles in good to excellent yields under mild reaction conditions.

  本报告介绍了一种从烯酰胺酯和硝基烯烃合成取代吡咯的简便而高效的方法。在温和的反应条件下，这种通用方法可提供多种多取代吡咯，收率从良好到极佳。
• Preparation, characterization and catalytic application of molybdenum Schiff-base complex immobilized on silica-coated Fe₃ O₄ as a reusable catalyst for the synthesis of pyranopyrazole derivatives
  作者：Seyedeh Aghigh Hamrahian、Sadegh Salehzadeh、Jamshid Rakhtshah、Farshid Haji babaei、Niloofar Karami

  DOI：10.1002/aoc.4723

  日期：2019.2

  A recoverable molybdenum Schiff‐base complex immobilized on silica‐coated Fe3O4 nanoparticles was prepared and characterized. This superparamagntic nanocatalyst, which is separable using an external magnet, can be used as an efficient catalyst for the promotion of the synthesis of pyranopyrazole derivatives. A variety of desired products were obtained in high to excellent yields within short times

  制备并表征了固定在二氧化硅涂层的Fe 3 O 4纳米颗粒上的可回收钼席夫碱复合物。可以使用外部磁体分离的这种超顺磁性纳米催化剂可以用作促进吡喃并吡唑衍生物的合成的有效催化剂。在短时间内以高产量至优异产量获得了各种所需产品。与在各种芳香醛，丙二腈和3-甲基-1-苯基-2-吡唑啉-5-酮的缩合反应中使用的其他催化剂相比，本催化剂在温和的条件和较短的反应时间下具有更高的活性。催化剂可以重复使用数次，而不会显着降低活性。