2-amino-4-(4-methylphenyl)-6-(4-chlorophenyl)nicotinonitrile | 642028-84-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-amino-4-(4-methylphenyl)-6-(4-chlorophenyl)nicotinonitrile
• 英文别名: 2-amino-6-(4-chlorophenyl)-4-(p-tolyl)nicotinonitrile；2-amino-6-(4-chlorophenyl)-4-(4-methylphenyl)pyridine-3-carbonitrile
• CAS: 642028-84-0
• 化学式: C₁₉H₁₄ClN₃
• 分子量: 319.793
• InChiKey: HJOGGPNHELJJNR-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  62.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  衣康酸 、 2-amino-4-(4-methylphenyl)-6-(4-chlorophenyl)nicotinonitrile 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 15.0h， 以64%的产率得到1-[6-(4-chlorophenyl)-3-cyano-4-(4-methylphenyl)pyridin-2-yl]-5-oxopyrrolidine-3-carboxylic acid
  参考文献：
  名称：

  吡啶基-吡咯烷酮抗惊厥活性的设计、合成和评价：一种药效团混合方法

  摘要：

  各种1-[6-(4-取代苯基)-3-氰基-4-(取代苯基)-吡啶-2-基]-5-氧代吡咯烷-3-羧酸(3a-t)被设计和合成吡咯烷酮和吡啶，两种活性抗惊厥药效团。所有合成的化合物均满足建议的抗惊厥活性药效模型的要求。他们的体内抗惊厥评估是通过最大电休克发作 (MES) 和皮下戊四唑 (scPTZ) 测试进行的。通过旋转棒试验评估了最小的运动损伤，并进行了各种肝酶的估计，以检查合成化合物造成的肝毒性的程度。化合物 3d 和 3k 显示出与标准药物相当的抗惊厥活性，在电击屏幕中的 ED50 值为 13.4 和 18.6 mg/kg，分别。还发现化合物 3d 和 3k 在 scPTZ 筛选中具有令人鼓舞的抗惊厥活性（ED50 分别为 86.1 和 271.6 mg/kg）。有趣的是，它们在给药的最大剂量下没有表现出任何运动障碍的迹象，并且对肝脏没有毒性。

  DOI：

  10.1002/ardp.201100140
• 作为产物：
  描述：

  1-(4-chlorophenyl)-3-(4-methylphenyl)prop-2-en-1-one 、 丙二腈 在 ammonium acetate 作用下， 以 乙醇 为溶剂， 生成 2-amino-4-(4-methylphenyl)-6-(4-chlorophenyl)nicotinonitrile
  参考文献：
  名称：

  Triarylimidazo[1,2-a]pyridine-8-carbonitriles: solvent-free synthesis and their anti-cancer evaluation

  摘要：

  In this study, we have presented the synthesis of novel 2,5,7-triarylimidazo[1,2-a]pyridine-8-carbonitriles from 2-amino-4,6-diarlypyridine-3-carbonitrile and nitrostyrene using FeCl3 (20 mol%) as Lewis acid under solvent-free conditions. A library of compounds with diverse substitutions have also been synthesized and screened for in-vitro anti-cancer activity against various cell lines such as A549 (Lung), HCT-116 (Colon), SW-620 (Colon), and MIAPACA (Pancreas).[GRAPHICS].

  DOI：

  10.1080/00397911.2019.1605445

文献信息

• Aqueous media preparation of 2-amino-4,6-diphenylnicotinonitriles using cellulose sulfuric acid as an efficient catalyst
  作者：Syed Sheik Mansoor、Krishnamoorthy Aswin、Kuppan Logaiya、Prasanna Nithiya Sudhan、Saleem Malik

  DOI：10.1007/s11164-012-1008-9

  日期：2014.2

  es via four-component reaction of aromatic aldehydes, acetophenone derivatives, malononitrile and ammonium acetate is described. The reactions were done in water as solvent using cellulose sulfuric acid as catalyst. This simple protocol offer advantages such as shorter reaction times, simple work-up procedure, excellent yields and catalyst recovery.

  描述了一种通过芳族醛，苯乙酮衍生物，丙二腈和乙酸铵的四组分反应合成2-氨基-4,6-二苯基烟腈的简便方法。反应以纤维素硫酸为催化剂，在水为溶剂中进行。这种简单的方案具有诸如缩短反应时间，简化后处理程序，优异的收率和催化剂回收率等优点。
• Novel magnetic nanoparticles with morpholine tags as multirole catalyst for synthesis of hexahydroquinolines and 2-amino-4,6-diphenylnicotinonitriles through vinylogous anomeric-based oxidation
  作者：Sima Kalhor、Meysam Yarie、Majid Rezaeivala、Mohammad Ali Zolfigol

  DOI：10.1007/s11164-019-03802-7

  日期：2019.6

  magnetometry (VSM). The catalytic performance of the novel nanomagnetic catalyst was examined in multicomponent preparation of hexahydroquinolines and 2-amino-4,6-diphenylnicotinonitriles through vinylogous anomeric-based oxidation under mild reaction conditions. Graphical abstract Novel magnetic nanoparticles with morpholine tags promoted synthesis of hexahydroquinolines and 2-amino-4,6-diphenylnicotinonitriles

  摘要 合成并表征了一种新型的带有吗啉标记的非均相纳米磁性催化剂。纳米磁性催化剂的形成已通过几种方法得到了充分证实，包括傅立叶变换红外（FT-IR）光谱，能量色散X射线（EDX）光谱，元素映射，X射线衍射（XRD）分析，扫描电子显微镜（SEM），透射电子显微镜（TEM），热重/衍生热重（TG / DTG）和振动样品磁强（VSM）。该新型纳米磁性催化剂的催化性能在六氢喹啉和2-氨基-4,6-二苯基烟腈的多组分制备中，通过在温和的反应条件下通过乙烯基异氰酸酯基氧化来检测。 图形概要 具有吗啉标记的新型磁性纳米粒子通过基于乙烯基异头物的氧化促进了六氢喹啉和2-氨基-4,6-二苯基烟腈的合成。
• One-pot synthesis of 2-amino-3-cyanopyridines and hexahydroquinolines using eggshell-based nano-magnetic solid acid catalyst via anomeric-based oxidation
  作者：Tahere Akbarpoor、Ardeshir Khazaei、Jaber Yousefi Seyf、Negin Sarmasti、Maryam Mahmoudiani Gilan

  DOI：10.1007/s11164-019-04049-y

  日期：2020.2

  In the present research, the eggshell as a hazardous waste by European Union regulations was converted to a valuable catalyst, namely nano-Fe3O4@(HSO4)2. The as-prepared catalyst, first, was characterized using different techniques, including Fourier-transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), energy-dispersive X-ray spectroscopy (EDX), field emission scanning electron microscopy (FESEM), and transmission electron microscopy (TEM). Back-titration method confirmed the loading of a high surface density of acidic group, namely 8.8 mmol HSO4 per gram of the catalyst. The catalytic property of the as-prepared catalyst was examined in the synthesis of 2-amino-3-cyanopyridines via anomeric-based oxidation (ABO), and hexahydroquinolines derivatives. High yield, short reaction time, solvent-free condition, waste to wealth, and optimization with the design of experiment are the major advantages of the present work. Taken together, these results suggest the conversion of waste to wealth products around the world and usage in organic transformation.

  在本项研究中，通过欧洲联盟法规界定为危险废物的蛋壳被转化为一种有价值的催化剂，即纳米Fe3O4@(HSO4)2。所制备的催化剂首先通过多种技术进行了表征，包括傅里叶变换红外光谱（FT-IR）、X射线衍射（XRD）、能量色散X射线光谱（EDX）、场发射扫描电子显微镜（FESEM）和透射电子显微镜（TEM）。反滴定法证实了催化剂表面存在高密度的酸性基团，具体为每克催化剂含有8.8 mmol HSO4。通过异头氧化（ABO）合成2-氨基-3-氰基吡啶以及六氢喹啉衍生物时，考察了所制备催化剂的催化性能。高产率、短反应时间、无溶剂条件、废物利用以及结合实验设计的优化是本工作的主要优势。综合来看，这些结果表明了废物在全球范围内的财富转化潜力，并可用于有机转化过程。
• Triarylimidazo[1,2-<i>a</i>]pyridine-8-carbonitriles: solvent-free synthesis and their anti-cancer evaluation
  作者：Annah Gupta、Sonakshi Sasan、Avneet Kour、Nargis Nelofar、Dilip Manikrao Mondhe、Kamal K. Kapoor

  DOI：10.1080/00397911.2019.1605445

  日期：2019.7.18

  In this study, we have presented the synthesis of novel 2,5,7-triarylimidazo[1,2-a]pyridine-8-carbonitriles from 2-amino-4,6-diarlypyridine-3-carbonitrile and nitrostyrene using FeCl3 (20 mol%) as Lewis acid under solvent-free conditions. A library of compounds with diverse substitutions have also been synthesized and screened for in-vitro anti-cancer activity against various cell lines such as A549 (Lung), HCT-116 (Colon), SW-620 (Colon), and MIAPACA (Pancreas).[GRAPHICS].
• Design, Synthesis and Evaluation of Anticonvulsant Activity of Pyridinyl-Pyrrolidones: A Pharmacophore Hybrid Approach
  作者：Nadeem Siddiqui、Waquar Ahsan、M. Shamsher Alam、Ruhi Ali、Kamna Srivastava

  DOI：10.1002/ardp.201100140

  日期：2012.3

  phenyl)‐pyridin‐2‐yl]‐5‐oxopyrrolidine‐3‐carboxylic acids (3a–t) were designed and synthesized by clubbing pyrrolidinones and pyridines, the two active anticonvulsant pharmacophores. All the synthesized compounds fulfilled the requirements of suggested pharmacophoric model for anticonvulsant activity. Their in vivo anticonvulsant evaluation was performed by maximal electroshock seizure (MES) and subcutaneous

  各种1-[6-(4-取代苯基)-3-氰基-4-(取代苯基)-吡啶-2-基]-5-氧代吡咯烷-3-羧酸(3a-t)被设计和合成吡咯烷酮和吡啶，两种活性抗惊厥药效团。所有合成的化合物均满足建议的抗惊厥活性药效模型的要求。他们的体内抗惊厥评估是通过最大电休克发作 (MES) 和皮下戊四唑 (scPTZ) 测试进行的。通过旋转棒试验评估了最小的运动损伤，并进行了各种肝酶的估计，以检查合成化合物造成的肝毒性的程度。化合物 3d 和 3k 显示出与标准药物相当的抗惊厥活性，在电击屏幕中的 ED50 值为 13.4 和 18.6 mg/kg，分别。还发现化合物 3d 和 3k 在 scPTZ 筛选中具有令人鼓舞的抗惊厥活性（ED50 分别为 86.1 和 271.6 mg/kg）。有趣的是，它们在给药的最大剂量下没有表现出任何运动障碍的迹象，并且对肝脏没有毒性。