N-(4-methoxyphenyl)-3,5-dinitropyridin-2-amine

• 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-methoxyphenyl)-3,5-dinitropyridin-2-amine
• 化学式: C₁₂H₁₀N₄O₅
• mdl: MFCD00579366
• 分子量: 290.235
• InChiKey: YISPASGPJIRBHA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  126
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  2-乙氧基-3,5-二硝基吡啶 、 甲氧苯胺 在 三乙烯二胺 作用下， 以 二甲基亚砜 为溶剂， 生成 N-(4-methoxyphenyl)-3,5-dinitropyridin-2-amine
  参考文献：
  名称：

  在DMSO中2-氯-3,5-二硝基吡啶和2-乙氧基-3,5-二硝基吡啶与对位取代苯胺反应中σ-加合物形成和亲核取代的动力学和平衡研究

  摘要：

  摘要在1,4-二氮杂双环[2.2.2]辛烷存在下2-氯-3,5-二硝基吡啶和2-乙氧基-3,5-二硝基吡啶与一系列对位取代苯胺反应的速率和平衡结果（DABCO）在DMSO中进行了研究。反应产生2-苯胺基-3,5-二硝基吡啶衍生物，并且分光光度法未检测到中间体的积累。该速率与两步机制兼容，该机制涉及最初的亲核攻击，然后是碱催化的或未催化的转化为产物。碱催化的途径可能涉及限速质子从两性离子中间体到碱的转移，以产生阴离子σ-加合物。对数p的log K 1 k DABCO的图K a值在25°C时具有良好的直线，2-氯-和0.4-5-（2-乙氧基-3,5-二硝基吡啶）的斜率。将结果与2-苯氧基-3,5-二硝基吡啶与取代苯胺的反应结果进行了比较。 图形概要

  DOI：

  10.1007/s00706-012-0860-z

文献信息

• The reaction of 2-phenoxy-3,5-dinitropyridine with substituted anilines in the presence of 1,4-diazabicyclo[2.2.2]octane in dimethyl sulfoxide: Kinetic and equilibrium studies
  作者：Basim H. Asghar

  DOI：10.1002/kin.20389

  日期：2009.3

  (4a–d) in dimethyl sulfoxide (DMSO) in the presence of 1,4‐diazabicyclo[2.2.2]octane (DABCO) yield the 2‐anilino derivatives without the accumulation of intermediates. The kinetics is compatible with a two‐step reaction involving initial nucleophilic attack followed by either base‐catalyzed or uncatalyzed conversion to the product. The base‐catalyzed pathway is likely to involve rate‐limiting proton transfer

  在1,4-二氮杂双环[2.2.2]辛烷（DABCO）存在下，2-苯氧基-3,5-二硝基吡啶（1）与一系列取代苯胺（4a-d）在二甲基亚砜（DMSO）中的反应产生2-苯胺基衍生物，而没有中间体的积累。该动力学与两步反应兼容，该反应涉及最初的亲核攻击，然后是碱催化的或未催化的转化为产物。碱催化的途径可能涉及限速质子从两性离子中间体向碱的转移。将结果与1,3,5-三硝基苯（2）和苯基2,4,6-三硝基苯醚（3，R = Ph）和苯胺。©2008 Wiley Periodicals，Inc.国际化学杂志Kinet 41：198–203，2009
• Kinetics of the reaction of 2-chloro-3,5-dinitropyridine withmeta- andpara-substituted anilines in methanol
  作者：Fatma El-Zahraa M. EL Hegazy、Soheir Z. Abdel Fattah、Ezzat A. Hamed、Saber M. Sharaf

  DOI：10.1002/1099-1395(200009)13:9<549::aid-poc297>3.0.co;2-5

  日期：2000.9

  The kinetics of the reaction of 2-chloro-3,5-dinitropyridine (1) with meta- and para-substituted anilines (2a–j) to give 2-anilino-3,5-dinitropyridine derivatives (3a–j) were studied in methanol at different temperatures. IR studies of the products (3a–j) indicated the presence of hydrogen bonding between N—H and an o-nitro group, and UV spectra showed a red shift resulting from the interaction between

  研究了 2-氯-3,5-二硝基吡啶 (1) 与间位和对位取代的苯胺 (2a-j) 反应生成 2-苯胺基-3,5-二硝基吡啶衍生物 (3a-j) 的动力学在不同温度的甲醇中。产物 (3a-j) 的 IR 研究表明，NH 和邻硝基之间存在氢键，紫外光谱显示由于氨基与氮杂和硝基之间的相互作用导致红移。ΔH‡ 与 ΔS‡ 的曲线图在 324 °C 等速温度下给出了良好的直线。在所有温度下，从 log k2 对 σ 值的图获得了良好的线性关系，具有相对较大的负 ρ 值（-3.75 到 -3.16），表明形成了 Meisenheimer σ-络合物中间体。log k2 与 pKa 值 (β = 0.85) 的关系图在 25 °C 时给出了良好的直线，除 2f (4-COCH3) 外，表明反应在过渡态中涉及显着的键形成。建议 SNAr 机制通过两个阶段进行，第一个阶段是速率确定。版权所有 © 2000 John
• Design and synthesis of diarylamines and diarylethers as cytotoxic antitumor agents
  作者：Xiao-Feng Wang、Xing-Tao Tian、Emika Ohkoshi、Bingjie Qin、Yi-Nan Liu、Pei-Chi Wu、Mann-Jen Hour、Hsin-Yi Hung、Keduo Qian、Rong Huang、Kenneth F. Bastow、William P. Janzen、Jian Jin、Susan L. Morris-Natschke、Kuo-Hsiung Lee、Lan Xie

  DOI：10.1016/j.bmcl.2012.08.014

  日期：2012.10

  Based on a shared structural core of diarylamine in several known anticancer drugs as well as a new cytotoxic hit 6-chloro-2-(4-cyanophenyl)amino-3-nitropyridine (7), 30 diarylamines and diarylethers were designed, synthesized, and evaluated for cytotoxic activity against A549, KB, KB-vin, and DU145 human tumor cell lines (HTCL). Four new leads 11e, 12, 13a, and 13b were discovered with GI(50) values ranging from 0.33 to 3.45 mu M. Preliminary SAR results revealed that a diarylamine or diarylether could serve as an active structural core, meta-chloro and ortho-nitro groups on the A-ring (either pyridine or phenyl ring) were necessary and crucial for cytotoxic activity, and the para-substituents on the other phenyl ring (B-ring) were related to inhibitory selectivity for different tumor cells. In an investigation of potential biological targets of the new leads, high thoughput kinase screening discovered that new leads 11e, 12 and 13b especially inhibit Mer tyrosine kinase, a proto-oncogene associated with munerous tumor types, with IC50 values of 2.2-3.0 mu M. Therefore, these findings provide a good starting point to optimize a new class of compounds as potential anticancer agents, particularly targeting Mer tyrosine kinase. (C) 2012 Elsevier Ltd. All rights reserved.
• Bhuvaneshwari; Elango, Journal of the Indian Chemical Society, 2011, vol. 88, # 10, p. 1547 - 1551
  作者：Bhuvaneshwari、Elango

  DOI：——

  日期：——