4-amino-6-(4-nitrophenyl)-2-phenylpyrimidine-5-carbonitrile | 777943-56-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 4-amino-6-(4-nitrophenyl)-2-phenylpyrimidine-5-carbonitrile
• CAS: 777943-56-3
• 化学式: C₁₇H₁₁N₅O₂
• 分子量: 317.307
• InChiKey: HWCZTQPNDKPQPV-UHFFFAOYSA-N

物化性质

• 熔点：
  215-216 °C(Solv: ethanol (64-17-5))
• 沸点：
  496.0±45.0 °C(Predicted)
• 密度：
  1.44±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-amino-6-(4-nitrophenyl)-2-phenylpyrimidine-5-carbonitrile 在 palladium on carbon 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 生成 4-amino-6-(p-aminophenyl)-5-cyano-2-phenylpyrimidine
  参考文献：
  名称：

  嘧啶衍生物的合成，抗胰酶活性和分子对接研究

  摘要：

  该出版物描述了28种嘧啶衍生物的合成，其中8种是新的。其结构已通过光谱技术（IR，H1，C13 NMR数据）验证。质谱分析正确给出了所有化合物的元素组成。已针对克鲁氏锥虫的两个不同阶段对所有28种化合物进行了体外评估：1.副鞭毛虫和2.鞭毛鞭毛虫。化合物3a，3b，3j，3k，3o，3s和5d表现出比苯并硝唑（BZN）更大的活性。化合物3a的选择性类似于BZN。使用对接方法进行分子建模以确定配体与酶的结合。使用GOLD 5.2程序进行的MO计算提供了有关该酶与嘧啶结合位点的信息。

  DOI：

  10.1007/s00044-018-2253-2
• 作为产物：
  描述：

  对硝基苯甲醛 以 甲醇 为溶剂， 反应 11.0h， 生成 4-amino-6-(4-nitrophenyl)-2-phenylpyrimidine-5-carbonitrile
  参考文献：
  名称：

  Synthesis and antiinflammatory activity of 4-amino-2-aryl-5-cyano-6-{3- and 4-(N-phthalimidophenyl)} pyrimidines

  摘要：

  Six new 4-amino-5-eyano-2,6-diarylpyrimidines 5a-h has been synthesized in a facile manner by reacting the appropriate arylamidines 4a-d with bisnitriles 3a-e. Reduction of the nitro group of 5a-e using Pd in ethyl acetate furnished 6a-e in good yields. Reaction of 6a-e individually with phthalic anhydride yielded 7a-e in good to excellent yields. The newly synthesized heterocycles were characterized by IR, H-1-NMR and mass spectral data. Compounds 5f-h and 7a-e were also evaluated against inflammation. Pyrimidines 5g, h exhibited better anti inflammatory activity when compared with acetylsalicylic acid (ASA). Phthalimide derivatives 7a-e also presented antiinflammatory activity, and three of them, viz., 7a-c have been found to be twice more active than aspirin. Cytotoxical evaluations of compounds 7a-e using neoplastic cells (NCI-H-292 and Hep-2) presented 41% of growth inhibition of neoplastic cells NCI-H-292. (c) 2006 Elsevier SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2005.09.009

文献信息

• A New Facile, High Yielding and Efficient Protocol for the Synthesis of Novel 4-Phenylsulfonamido-6-Aryl-2-Phenylpyrimidine-5-Carbonitrile Derivatives
  作者：Reza Aryan、Masoomeh Nojavan、Fatemeh Sadeghi

  DOI：10.1080/10426507.2015.1050017

  日期：2015.11.2

  GRAPHICAL ABSTRACT Abstract A series of novel 4-phenylsulfonamido-6-aryl-2-phenylpyrimidine-5-carbonitrile derivatives have been synthesized through a two-step process. This protocol includes a facile surfactant-mediated methodology for the synthesis of 4-amino-6-aryl-2-phenylpyrimidine-5-carbonitrile derivatives through a one-pot, three-component reaction in the presence of a catalytic amount of

  图形摘要 摘要 通过两步法合成了一系列新型 4-苯基磺酰氨基-6-芳基-2-苯基嘧啶-5-甲腈衍生物。该协议包括一种简便的表面活性剂介导方法，用于在催化量的十六烷基三甲基溴化铵存在下通过一锅三组分反应合成 4-氨基-6-芳基-2-苯基嘧啶-5-腈衍生物。水。没有使用额外的有机溶剂和氧化剂。然后在四氢呋喃溶液中在氢化钠的存在下将嘧啶-5-甲腈产物进行4-氨基直接磺酰化成4-苯基磺酰胺-6-芳基-2-苯基嘧啶-5-甲腈衍生物。这些新结构通过 1H 和 13CNMR 光谱以及质谱和元素分析得到证实。
• A Facile Synthesis of New Pyrazolo[3,4-<i>d</i>]pyrimidine Derivatives<i>via</i>a One-Pot Four-Component Reaction with Sodium Acetate Supported on Basic Alumina as Promoter
  作者：Shahnaz Rostamizadeh、Masoomeh Nojavan、Reza Aryan、Elyass Isapoor

  DOI：10.1002/hlca.201300060

  日期：2013.12

  efficient one‐pot procedure for the synthesis of 3‐amino‐6‐aryl‐2‐phenylpyrazolo[3,4‐d]pyrimidine derivatives, through the reaction of aldehydes, malononitrile, benzamidine hydrochloride, and hydrazine hydrate in the presence of basic alumina‐supported sodium acetate (AcONa/Al2O3) under reflux conditions, is reported. This protocol has some advantages, including the use of a simple and one‐pot synthetic

  在碱性条件下，通过醛，丙二腈，苯甲hydro盐酸盐和水合肼的反应，可以有效地合成3-氨基-6-芳基-2-苯基吡唑并[3,4- d ]嘧啶衍生物的一锅法据报道，在回流条件下氧化铝负载的乙酸钠（AcONa / Al 2 O 3）。该方案具有一些优点，包括使用简单的单锅合成方法直接从四种容易获得的起始原料中获得吡唑并[3,4- d ]嘧啶，简单的后处理，产品的高总收率以及同时进行NO 2转化为氨基，提供了合成更复杂结构的机会。
• A novel and efficient synthesis of pyrazolo[3,4-d]pyrimidine derivatives and the study of their anti-bacterial activity
  作者：Shahnaz Rostamizadeh、Masoomeh Nojavan、Reza Aryan、Hamid Sadeghian、Mahdieh Davoodnejad

  DOI：10.1016/j.cclet.2013.04.035

  日期：2013.7

  4-amino-6-aryl-2-phenyl pyrimidine-5-carbonitrile derivatives were synthesized through a one-pot, three-component reaction of an aldehyde, malononitrile and benzamidine hydrochloride, in the presence of magnetic nano Fe3O4 particles as a catalyst under solvent-free conditions. 3-Amino-6-aryl-2-phenylpyrazolo[3,4-d]pyrimidine derivatives were prepared through an efficient and environmentally friendly reaction between

  在这项工作中，在磁性纳米Fe 3 O的存在下，通过醛，丙二腈和苯甲idine盐酸盐的一锅三组分反应，合成了4-氨基-6-芳基-2-苯基嘧啶-5-甲腈衍生物。在无溶剂条件下有4个颗粒作为催化剂。3-氨基-6-芳基-2-苯基吡唑并[3,4- d ]嘧啶衍生物是通过4-氨基-6-芳基-2-苯基嘧啶-5-甲腈衍生物与水合肼和已对其抗菌活性进行了评估。
• One-step synthesis of aminopyrimidines from 5-Oxo-4<i>H</i>-benzopyrans
  作者：Esperanza Salfrán、Carlos Seoaneb、Margarita Suárez、Yamila Verdecia、Amaury Alvarez、Estael Ochoa、Roberto Martínez-Alvarez、Nazario Martín

  DOI：10.1002/jhet.5570410406

  日期：2004.7

  4-amino-6-aryl-2-phenylpyrimidine-5-carbonitriles have been prepared in one step procedure from the readily available 4-aryl-2-amino-3-cyano-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4H-benzopyrans. The mass spectroscopy study under EI conditions shows molecular peaks with high intensity corresponding to the loss of benzonitrile from the C2 position of the pyrimidine ring. Semiempirical (AMI and PM3) and ab initio

  一种新的4-氨基-6-芳基-2-苯基嘧啶-5-腈是从容易获得的4-芳基-2-氨基-3-氰基-5,6,7,8-四氢-7一步制备的。 ，7-二甲基-5-氧代-4 H-苯并吡喃。在EI条件下进行的质谱研究表明，具有高强度的分子峰对应于从嘧啶环的C2位上苯甲腈的损失。半经验（AMI和PM3）和从头开始的HF / 6-31G *计算显示了三个环不在同一平面上时偏爱的扭曲几何形状。
• Synthesis of 4-amino-2,6-diaryl-5-cyanopyrimidines as antimicrobial agents
  作者：Zenaide Severina do Monte、Maria Renata Leite Monteiro、Camila Beatriz Atanásio Borba、Norma Buarque de Gusmão、Emerson Peter da Silva Falcão、Ricardo Oliveira Silva、Rajendra M. Srivastava、Sebastião José de Melo

  DOI：10.1080/00397911.2016.1151051

  日期：2016.6.2

  and arylamidines in the presence of a base was clarified. A preliminary screening of the antibacterial tests clearly showed that 4 out of 11 pyrimidines, 3a, 3e, 3f, and 3k, were effective against bacteria Staphyloccus aureus, Bacillus subtillis, and Pseudomonas aeruginosa. Further, the minimum inhibitory concentration (MIC) against the bacteria has been determined. GRAPHICAL ABSTRACT

  摘要 本文描述了一种以间位和对位取代的 2-氰基肉桂腈和芳脒为原料，高效、简便地合成 11 种 2,4,6-三取代 5-氰基嘧啶的方法。合成的杂环化合物 3a-k 通过红外 (IR)、1H NMR、13C NMR 和质谱数据进行表征。阐明了在碱存在下使用 2-氰基肉桂腈和芳脒形成标题化合物的可能机制。抗菌试验的初步筛选清楚地表明，11 种嘧啶中的 4 种，3a、3e、3f 和 3k，对金黄色葡萄球菌、枯草芽孢杆菌和铜绿假单胞菌有效。此外，已经确定了对细菌的最小抑制浓度 (MIC)。图形概要