N-(4-chlorobenzyl)-4'-fluoroaniline | 80143-74-4

• 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: N-(4-chlorobenzyl)-4'-fluoroaniline
• 英文别名: 4-Chloro-N-(4-fluorophenyl)benzenemethanamine；N-[(4-chlorophenyl)methyl]-4-fluoroaniline
• CAS: 80143-74-4
• 化学式: C₁₃H₁₁ClFN
• mdl: MFCD03210843
• 分子量: 235.688
• InChiKey: PYPLTHRBFCMNSK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  12
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  反丁烯二酰氯 、 N-(4-chlorobenzyl)-4'-fluoroaniline 在 三乙胺 作用下， 以 乙酸乙酯 为溶剂， 反应 12.0h， 生成 but-2-enedioic acid bis[(4-chlorobenzyl)(4-fluorophenyl)amide]
  参考文献：
  名称：

  Preparation, anticholinesterase activity, and docking study of new 2-butenediamide and oxalamide derivatives

  摘要：

  Several new oxalamide and 2-butenediamide derivatives have been designed, synthesized and evaluated as the acetyl- and butyryl-cholinesterase inhibitors for Alzheimer's disease. The enzyme inhibitory activity of the synthesized compounds was measured using Ellman's colorimetric method. It was revealed that compound 1a (N, N'-bis-(4-chloro-benzyl)-N, N'-diphenyl-oxalamide) showed maximum activity against BuChE with a half maximal inhibitory concentration (IC50) = 1.86 mu M and compound 2a (but-2-enedioic acid bis-[(4-chloro-benzyl)-phenyl-amide]) exhibited optimum AChE (IC50 = 1.51 mu M) inhibition with a high-selectivity index. To better understand the enzyme-inhibitor interaction of the most active compounds towards cholinesterase, molecular modelling studies were carried out. Docking simulations revealed that inhibitors 1a and 2a targeted both the catalytic active site and the peripheral anionic site of 1ACJ and 1P0I.

  DOI：

  10.3109/14756366.2014.959947
• 作为产物：
  描述：

  N-(4-chlorobenzylidene)-4-fluoroaniline 在 对氟苯硫酚 作用下， 以 甲苯 为溶剂， 反应 8.0h， 以81%的产率得到N-(4-chlorobenzyl)-4'-fluoroaniline
  参考文献：
  名称：

  量子点作为催化剂通过转移加氢从亚胺上可见光光催化合成胺

  摘要：

  CdSe / CdS核/壳量子点（QDs）可以用作稳定和高活性的光氧化还原催化剂，用于以硫酚为氢原子供体的亚胺有效转移加氢成胺。该反应通过从QDs导带到质子化的亚胺的质子偶联电子转移（PCET）进行，然后氢原子从苯硫酚转移到α-氨基烷基。这种无贵金属的转化很容易扩大规模，可以通过一锅法直接从醛，胺和苯硫酚中进行。该方案的其他优势包括：广泛的底物范围，胺产物的高收率，极低的催化剂负载量（0.001 mol％），高周转率（10 5），以及在室温下在中性介质中使用可见光或阳光的温和反应条件。

  DOI：

  10.1021/acs.joc.8b01651

文献信息

• Synthesis of N-benzyl-N-phenylthiophene-2-carboxamide analogues as a novel class of enterovirus 71 inhibitors
  作者：Jiawei Pan、Xin Han、Ningyuan Sun、Haoming Wu、Dandan Lin、Po Tien、Hai-Bing Zhou、Shuwen Wu

  DOI：10.1039/c5ra07286g

  日期：——

  A series ofN-benzyl-N-phenylthiophene-2-carboxamide analogues were identified as novel human enterovirus 71 inhibitors with EC₅₀values up to 1.42 μM.

  一系列N-苄基-N-苯基噻吩-2-羧酰胺类似物被确定为新型人类肠道病毒71抑制剂，EC50值高达1.42μM。
• 1,2,3-Triazole-boranes: stable and efficient reagents for ketone and aldehyde reductive amination in organic solvents or in water
  作者：Wenyan Liao、Yunfeng Chen、Yuxiu Liu、Haifeng Duan、Jeffrey L. Petersen、Xiaodong Shi

  DOI：10.1039/b915361f

  日期：——

  Air, moisture and thermally stable 1,2,3-triazole-borane complexes were developed as new practical reagents for ketone/aldehyde amination with high efficiency and excellent substrate diversity.

  空气，水分和热稳定的1,2,3-三唑-硼烷配合物被开发为高效/高效的酮/醛胺化的新型实用试剂，并且具有出色的底物多样性。
• New benzamide derivatives and their nicotinamide/cinnamamide analogs as cholinesterase inhibitors
  作者：Mehmet Koca、Sinan Bilginer

  DOI：10.1007/s11030-021-10249-9

  日期：2022.4

  In this study, a total of 18 new benzamide/ nicotinamide/ cinnamamide derivative compounds were designed and synthesized for the first time (except B1 and B5) by conventional and microwave irradiation methods. The chemical structures of the synthesized compounds were characterized by 1H NMR, 13C NMR, and HRMS spectra. In vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibition

  本研究通过常规和微波辐照方法，首次设计合成了18个苯甲酰胺/烟酰胺/肉桂酰胺新衍生物化合物（B1和B5除外）。合成化合物的化学结构通过1 H NMR、13C NMR和HRMS光谱。评估了化合物的体外乙酰胆碱酯酶 (AChE) 和丁酰胆碱酯酶 (BuChE) 抑制作用，以找出新的可能的候选药物分子。根据抑制结果，合成的化合物对AChE的IC50值在10.66-83.03 nM范围内，而对BuChE的IC50值在32.74-66.68 nM范围内。他克林用作参比药物，其对 AChE 和 BuChE 的 IC50 值分别为 20.85 nM 和 15.66 nM。各系列对乙酰胆碱酯酶活性最强的化合物B4（IC50：15.42 nM）、N4（IC50：12.14 nM）和C4（IC50：10.67 nM）对接在AChE酶的结合位点，解释各系列的抑制活性. 另一方面，化合物 B4、N4、 图形摘要
• Synthesis, structural elucidation and in vitro antiparasitic activity against Trypanosoma cruzi and Leishmania chagasi parasites of novel tetrahydro-1-benzazepine derivatives
  作者：Sandra Gómez-Ayala、Julián A. Castrillón、Alirio Palma、Sandra M. Leal、Patricia Escobar、Alí Bahsas

  DOI：10.1016/j.bmc.2010.05.018

  日期：2010.7

  Forty six new 1,4-epoxy-2-exo-aryl-and cis-2-aryl-4-hydroxytetrahydro-1-benzazepine derivatives were synthesized and fully characterized. All compounds were tested in vitro against both Trypanosoma cruzi and Leishmania chagasi parasites and also for cytotoxicity using Vero and THP-1 mammalian cell lines. Many of the evaluated compounds showed remarkable activity against the epimastigote and intracellular amastigote forms of T. cruzi, with IC50 values comparable with that of control drug nifurtimox, a nitrofuran derivative currently used in the treatment of Chagas' disease. Other derivatives were found to have good activity against L. chagasi promastigotes, with low toxicity against the mammalian cells, but neither of them was active on intracellular amastigotes of L. chagasi infecting THP-1 macrophages. (C) 2010 Elsevier Ltd. All rights reserved.
• Study of comparative transmission capacity of C-N bond by19F NMR method
  作者：S. I. Pombrik、E. V. Polunkin、A. S. Peregudov、D. N. Kravtsov、�. I. Fedin

  DOI：10.1007/bf00963450

  日期：1981.10