N-(3-methylbenzyl)-2-nitroaniline | 954226-14-3

• 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-(3-methylbenzyl)-2-nitroaniline
• 英文别名: N-[(3-methylphenyl)methyl]-2-nitroaniline
• CAS: 954226-14-3
• 化学式: C₁₄H₁₄N₂O₂
• mdl: MFCD09862620
• 分子量: 242.277
• InChiKey: QKQZGMFLNBDUAQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.142
• 拓扑面积：
  57.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(3-methylbenzyl)-2-nitroaniline 在 sodium dithionite 作用下， 以 乙醇 、 水 为溶剂， 反应 6.0h， 以3.1 g的产率得到N-(3-methylbenzyl)benzene-1,2-diamine
  参考文献：
  名称：

  High-Throughput-Screening-Based Identification and Structure–Activity Relationship Characterization Defined (S)-2-(1-Aminoisobutyl)-1-(3-chlorobenzyl)benzimidazole as a Highly Antimycotic Agent Nontoxic to Cell Lines

  摘要：

  Novel nontoxic (S)-2-aminoalkylbenzimidazole derivatives were found to be effective against Candida spp. at low micromolar concentrations using high-throughput screening with infected HeLa cells. A collection of analogues defined the chemical groups relevant for activity. The most active compound was characterized by transcriptional analysis of the response of C. albicans Sc5314. (S)-2-(1-Aminoisobutyl)-1-(3-chlorobenzyl)benzimidazole had a strong impact on membrane biosynthesis. Testing different clinically relevant pathogenic fungi showed the selectivity of the antimycotic activity against Candida species.

  DOI：

  10.1021/jm200571e
• 作为产物：
  描述：

  3-甲基苄胺 、 1-氟-2-硝基苯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 生成 N-(3-methylbenzyl)-2-nitroaniline
  参考文献：
  名称：

  High-Throughput-Screening-Based Identification and Structure–Activity Relationship Characterization Defined (S)-2-(1-Aminoisobutyl)-1-(3-chlorobenzyl)benzimidazole as a Highly Antimycotic Agent Nontoxic to Cell Lines

  摘要：

  Novel nontoxic (S)-2-aminoalkylbenzimidazole derivatives were found to be effective against Candida spp. at low micromolar concentrations using high-throughput screening with infected HeLa cells. A collection of analogues defined the chemical groups relevant for activity. The most active compound was characterized by transcriptional analysis of the response of C. albicans Sc5314. (S)-2-(1-Aminoisobutyl)-1-(3-chlorobenzyl)benzimidazole had a strong impact on membrane biosynthesis. Testing different clinically relevant pathogenic fungi showed the selectivity of the antimycotic activity against Candida species.

  DOI：

  10.1021/jm200571e

文献信息

• High-Throughput-Screening-Based Identification and Structure–Activity Relationship Characterization Defined (<i>S</i>)-2-(1-Aminoisobutyl)-1-(3-chlorobenzyl)benzimidazole as a Highly Antimycotic Agent Nontoxic to Cell Lines
  作者：Jörg Bauer、Stephan Kinast、Anke Burger-Kentischer、Doris Finkelmeier、Gerald Kleymann、Walid Abu Rayyan、Klaus Schröppel、Anurag Singh、Günther Jung、Karl-Heinz Wiesmüller、Steffen Rupp、Holger Eickhoff

  DOI：10.1021/jm200571e

  日期：2011.10.13

  Novel nontoxic (S)-2-aminoalkylbenzimidazole derivatives were found to be effective against Candida spp. at low micromolar concentrations using high-throughput screening with infected HeLa cells. A collection of analogues defined the chemical groups relevant for activity. The most active compound was characterized by transcriptional analysis of the response of C. albicans Sc5314. (S)-2-(1-Aminoisobutyl)-1-(3-chlorobenzyl)benzimidazole had a strong impact on membrane biosynthesis. Testing different clinically relevant pathogenic fungi showed the selectivity of the antimycotic activity against Candida species.
• [DE] NEUE BENZIMIDAZOL-2-YL-ALKYLAMINE UND IHRE ANWENDUNG ALS MIKROBIZIDE WIRKSTOFFE<br/>[EN] NOVEL BENZIMIDAZOL-2-YL-ALKYLAMINES AND THE USE THEREOF AS MICROBICIDAL AGENTS<br/>[FR] NOUVELLES BENZIMIDAZOL-2-YL-ALKYLAMINES ET LEUR UTILISATION EN TANT QUE SUBSTANCES ACTIVES MICROBICIDES
  申请人：EMC MICROCOLLECTIONS GMBH

  公开号：WO2009019014A1

  公开（公告）日：2009-02-12

  Die vorliegende Erfindung betrifft neue Benzimidazol-2-yl-alkylamine, welche antimikrobielle Eigenschaften aufweisen, Verfahren zur Herstellung dieser Verbindungen, sowie ihre Anwendung als mikrobizide Wirkstoffe in pharmazeutischen Präparaten oder Pflanzenschutzmitteln. Obwohl zahlreiche mikrobizide Wirkstoffe bekannt sind, ergibt sich aufgrund der Anpassungsfähigkeit der Mikroorganismen und der damit verbundenen Ausbildung von Resistenzen ein ständiger Bedarf an neuen, hochwirksamen, aber auch physiologisch verträglichen Substanzen mit möglichst neuartigen Wirkmechanismen sowie breiteren Wirkungsspektren. Die beschriebenen Benzimidazol-Dehvate der unten angegebenen Formel weisen eine gute antimikrobielle Wirkung insbesondere gegenüber Spezies der Gattung Candida auf. Toxizitätstests ergaben eine gute Verträglichkeit der neuen Wirkstoffe. Zur Herstellung der Verbindungen werden zwei verschiedene Verfahren beschrieben. Die Verbindungen werden zur systemischen und lokalen Behandlung von Menschen, Tieren und Pflanzen, die mit schädlichen Mikroorganismen, insbesondere Pilzen, Bakterien, Viren, Algen, Protozoen und anderen Parasiten befallen sind, eingesetzt (Formel I).
• Discovery of isoalloxazine derivatives as a new class of potential anti-Alzheimer agents and their synthesis
  作者：Ashish M. Kanhed、Anshuman Sinha、Jatin Machhi、Ashutosh Tripathi、Zalak S. Parikh、Prakash P. Pillai、Rajani Giridhar、Mange Ram Yadav

  DOI：10.1016/j.bioorg.2015.05.005

  日期：2015.8

  This article describes discovery of a novel and new class of cholinesterase inhibitors as potential therapeutics for Alzheimer's disease. A series of novel isoalloxazine derivatives were synthesized and biologically evaluated for their potential inhibitory outcome for both acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE). These compounds exhibited high activity against both the enzymes AChE as well as BuChE. Of the synthesized compounds, the most potent isoalloxazine derivatives (7m and 7q) showed IC50 values of 4.72 mu M and 5.22 mu M respectively against AChE; and, 6.98 mu M and 5.29 mu M respectively against BuChE. These two compounds were further evaluated for their anti-aggregatory activity for beta-amyloid (A beta) in presence and absence of AChE by performing Thioflavin-T (ThT) assay and Congo red (CR) binding assay. In order to evaluate cytotoxic profile of these two potential compounds, cell viability assay of SH-SY5Y human neuroblastoma cells was performed. Further, to understand the binding behavior of these two compounds with AChE and BuChE enzymes, docking studies have been reported. (C) 2015 Elsevier Inc. All rights reserved.