4-(1H-吡咯-1-甲基)苯甲酸 | 137025-10-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 4-(1H-吡咯-1-甲基)苯甲酸
• 英文名称: 4-(1H-pyrrol-1-ylmethyl)benzoic acid
• 英文别名: 4-(pyrrol-1-ylmethyl)benzoic acid；4-N-pyrrolomethylbenzoic acid；N-(4-carboxybenzyl)pyrrole
• CAS: 137025-10-6
• 化学式: C₁₂H₁₁NO₂
• mdl: MFCD04354173
• 分子量: 201.225
• InChiKey: BVJRENXLDBXRHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  42.2
• 氢给体数：
  1
• 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：

  4-(1H-吡咯-1-甲基)苯甲酸 在 盐酸 、 氢氧化钾 、 四氯化锡 、 potassium carbonate 、 一水合肼 作用下， 以 丙酮 、 苯 为溶剂， 反应 8.0h， 生成 4-(3-Octadecyl-pyrrol-1-ylmethyl)-benzoic acid
  参考文献：
  名称：

  PREPARATION OF 3-LONG-CHAIN SUBSTITUTED 5-MEMBERED HETEROARYLENES AND STUDIES OF THEIR LANGMUIR-BLODGETT FILM FORMATION

  摘要：

  The synthesis of amphiphilic thiophene 1 and pyrrole 5 were achieved via Wittig and Friedel-Crafts reactions respectively. The ability of 1 and 5, as well as 3-heptadecylthiophene and poly(3-heptadecylthiophene), to form Langmuir-Blodgett films are discussed.

  DOI：

  10.1080/10426509608037961
• 作为产物：
  描述：

  methyl 4-((1H-pyrrol-1-yl)methyl)benzoate 在 水 、 sodium hydroxide 作用下， 反应 24.0h， 以94%的产率得到4-(1H-吡咯-1-甲基)苯甲酸
  参考文献：
  名称：

  具有改善的抗真菌活性的苯甲酸衍生物：设计，合成，构效关系（SAR）和CYP53对接研究。

  摘要：

  以前，我们将CYP53鉴定为天然酚类抗真菌化合物的真菌特异性靶标，并发现了几种具有抗真菌特性的抑制剂。在这项研究中，我们进行了基于相似度的虚拟筛选和合成以获得苯甲酸衍生的化合物，并评估了它们对Cochliobolus lunatus，黑曲霉和平菇的抗真菌活性。。此外，我们生成了CYP53酶的结构模型，并将其用于与40种选定化合物的对接试验。最后，我们探索了CYP53与配体的相互作用，并确定了赋予抗真菌活性增强的结构元件，以促进潜在针对动物和植物病原性真菌CYP53酶的新型抗真菌剂的开发。

  DOI：

  10.1016/j.bmc.2015.06.042

文献信息

• Discovery of an MLLT1/3 YEATS Domain Chemical Probe
  作者：Moses Moustakim、Thomas Christott、Octovia P. Monteiro、James Bennett、Charline Giroud、Jennifer Ward、Catherine M. Rogers、Paul Smith、Ioanna Panagakou、Laura Díaz-Sáez、Suet Ling Felce、Vicki Gamble、Carina Gileadi、Nadia Halidi、David Heidenreich、Apirat Chaikuad、Stefan Knapp、Kilian V. M. Huber、Gillian Farnie、Jag Heer、Nenad Manevski、Gennady Poda、Rima Al-awar、Darren J. Dixon、Paul E. Brennan、Oleg Fedorov

  DOI：10.1002/anie.201810617

  日期：2018.12.10

  YEATS domain (YD) containing proteins are an emerging class of epigenetic targets in drug discovery. Dysregulation of these modified lysine-binding proteins has been linked to the onset and progression of cancers. We herein report the discovery and characterisation of the first small-molecule chemical probe, SGC-iMLLT, for the YD of MLLT1 (ENL/YEATS1) and MLLT3 (AF9/YEATS3). SGC-iMLLT is a potent and

  包含YEATS域（YD）的蛋白质是药物发现中新兴的表观遗传学目标。这些修饰的赖氨酸结合蛋白的失调与癌症的发生和发展有关。我们在此报告了针对MLLT1（ENL / YEATS1）和MLLT3（AF9 / YEATS3）的YD的第一个小分子化学探针SGC-iMLLT的发现和表征。SGC-iMLLT是一种有效且选择性的MLLT1 / 3-组蛋白相互作用抑制剂。观察到对其他人类YD蛋白（YEATS2 / 4）和溴结构域具有出色的选择性。此外，我们的探针显示了MLLT1和MLLT3的细胞靶标接合。还报道了具有MLLT1 YD的第一个小分子X射线共晶体结构。
• Design, Synthesis, and Biological Evaluation of <i>N</i>-Carboxyphenylpyrrole Derivatives as Potent HIV Fusion Inhibitors Targeting gp41
  作者：Kun Liu、Hong Lu、Ling Hou、Zhi Qi、Cátia Teixeira、Florent Barbault、Bo-Tao Fan、Shuwen Liu、Shibo Jiang、Lan Xie

  DOI：10.1021/jm800869t

  日期：2008.12.25

  On the basis of the structures of small-molecule hits targeting the HIV-1 gp41, N-(4-carboxy-3-hydi-oxy)plieiiyl-2,5-dimethylpyl-role (2, NB-2), and N-(3-carboxy-4-chloro)phenylpyrrole (A(1), NB-64), 42 N-carboxyphenylpyrrole derivatives in two categories (A and B series) were designed and synthesized. We found that I I compounds exhibited promising anti-HIV-1 activity at micromolar level and their antiviral activity was correlated with their inhibitory activity on gp41 six-helix bundle formation, suggesting that these compounds block HIV fusion and entry by disrupting gp41 core formation. The structure-activity relationship and molecular docking analysis revealed that the carboxyl group Could interact with either Arg579 or Lys574 to form salt bridges and two methyl groups on the pyrrole ring were favorable for interaction with the residues in gp41 pocket. The most active compound, N-(3-carboxy-4-hydroxy)phenyl-2,5-dimethylpyrrole (A(12)), partially occupied the deep hydrophobic pocket, suggesting that enlarging the molecular size of A(12) could improve its binding affinity and anti-HIV-1 activity for further development as a small-molecule HIV fusion and entry inhibitor.
• Aromatic hydrazides as specific inhibitors of bovine serum amine oxidase
  作者：M Artico、R Silvestri、G Stefancich、L Avigliano、A Di Giulio、M Maccarrone、E Agostinelli、B Mondovi、L Morpurgo

  DOI：10.1016/0223-5234(92)90005-l

  日期：1992.4

  New hydrazides were synthesized in search for specific inhibitors of bovine serum amine oxidase: a series of benzoic and phenylacetic acid hydrazides containing the 1H-imidazol-1-yl or the 1H-imidazol-1-ylmethyl group as (o, m, p)-substituent in the phenyl ring; an analogous series of p-substituted phenylhydrazides with 5 or 6-membered heterocyclic ring as substituent, and a series of similar phenylpropionic hydrazides. The longer and more flexible phenylacetic hydrazides, and to a somewhat lesser extent the phenylpropionic ones, were better specific inhibitors of bovine serum amine oxidase than the benzoic hydrazides, which were also bound by the enzyme with high affinity, but at a slow rate. Derivatives with p- and m -substituents were more reactive than the o-substituted ones. The chemical nature of the substituent was less important than its position in the phenyl ring and the presence of methylene spacers. These data point to the presence of a hydrophobic site at short distance from the protein carbonyl cofactor, so that simultaneous interaction of the 2 ends of the inhibitor molecule can occur at the 2 sites. The presence of the hydrophobic site was confirmed by the capability of some molecule deprived of the hydrazidic group to act as mild inhibitors. All hydrazides were less reactive by 2-3 orders of magnitude towards pig kidney diamine oxidase and FAD-dependent monoamine oxidase from rat brain mitochondria, while the other compounds showed similar inhibition power against all proteins. The specificity for the bovine enzyme seems therefore to be related to the concerted action of the 2 moieties of the inhibitor molecule.
• Silvestri; Pagnozzi; Valoti, Il Farmaco, 1994, vol. 49, # 10, p. 625 - 632
  作者：Silvestri、Pagnozzi、Valoti、Fusi

  DOI：——

  日期：——
• Benzoic acid derivatives with improved antifungal activity: Design, synthesis, structure–activity relationship (SAR) and CYP53 docking studies
  作者：Sabina Berne、Lidija Kovačič、Matej Sova、Nada Kraševec、Stanislav Gobec、Igor Križaj、Radovan Komel

  DOI：10.1016/j.bmc.2015.06.042

  日期：2015.8

  fungal-specific target of natural phenolic antifungal compounds and discovered several inhibitors with antifungal properties. In this study, we performed similarity-based virtual screening and synthesis to obtain benzoic acid-derived compounds and assessed their antifungal activity against Cochliobolus lunatus, Aspergillus niger and Pleurotus ostreatus. In addition, we generated structural models of CYP53 enzyme

  以前，我们将CYP53鉴定为天然酚类抗真菌化合物的真菌特异性靶标，并发现了几种具有抗真菌特性的抑制剂。在这项研究中，我们进行了基于相似度的虚拟筛选和合成以获得苯甲酸衍生的化合物，并评估了它们对Cochliobolus lunatus，黑曲霉和平菇的抗真菌活性。。此外，我们生成了CYP53酶的结构模型，并将其用于与40种选定化合物的对接试验。最后，我们探索了CYP53与配体的相互作用，并确定了赋予抗真菌活性增强的结构元件，以促进潜在针对动物和植物病原性真菌CYP53酶的新型抗真菌剂的开发。