2-amino-6-hydroxy-4-(4-hydroxyphenyl)pyrimidine-5-carbonitrile | 1160740-50-0

• 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: 2-amino-6-hydroxy-4-(4-hydroxyphenyl)pyrimidine-5-carbonitrile
• 英文别名: 2-amino-4-hydroxy-6-(4-hydroxyphenyl)pyrimidine-5-carbonitrile；2-amino-4-(4-hydroxyphenyl)-6-oxo-1H-pyrimidine-5-carbonitrile
• CAS: 1160740-50-0
• 化学式: C₁₁H₈N₄O₂
• 分子量: 228.21
• InChiKey: UDYLYLYSBYLZEO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.1
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  112
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氯甲基苯并咪唑 、 2-amino-6-hydroxy-4-(4-hydroxyphenyl)pyrimidine-5-carbonitrile 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 以78%的产率得到2-((1H-benzo[d]imidazol-2-yl)methylamino)-1,6-dihydro-4-(4-hydroxyphenyl)-6-oxopyrimidine-5-carbonitrile
  参考文献：
  名称：

  新型苯并咪唑衍生物作为丙型肝炎病毒RNA复制抑制剂的合成，分子建模和生物学评估。

  摘要：

  在这项研究中，进行了一系列新的苯并咪唑衍生物的合成和对接研究，这些衍生物通过亚甲基硫键或其生物等位亚甲基氨基桥与取代的嘧啶连接。评价所有合成的化合物的丙型肝炎病毒（HCV）RNA复制抑制活性。发现化合物4d，4f和4h比VX-950更有效（IC50 / 90为4d = 0.123 / 0.321、4f = 0.145 / 0.345、4h = 0.129 / 0.432，VX-950 = 0.20 / 0.45 µM ）和6d（IC50 / 90 = 0.116 / 0.452 µM）所显示的活性与标准品非常相似。化合物4d，4f，4h和6d是有效的HCV RNA复制抑制剂，是进一步研究的良好候选药物。

  DOI：

  10.1248/cpb.c13-01009
• 作为产物：
  描述：

  碳酸胍 、 对羟基苯甲醛 、 氰乙酸乙酯 在 NH₂-SBA-15 mesoporous silica 作用下， 以 乙醇 为溶剂， 反应 3.17h， 以67%的产率得到2-amino-6-hydroxy-4-(4-hydroxyphenyl)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  Amino-functionalized SBA-15 catalyzed one-step synthesis of 2-amino-5-cyano-4-hydroxy-6-aryl pyrimidines

  摘要：

  现已开发出一种简单高效的方法，可一步合成 2-氨基-5-氰基-4-羟基-6-芳基嘧啶。该方法基于脂肪族、芳香族或杂环醛、氰乙酸乙酯和碳酸胍在氨基官能化 SBA-15 催化剂存在下于乙醇中的三组分缩合。在这一化学过程中，观察到了嘧啶衍生物的同分异构体相互转化。这种高效的技术具有利用异相催化剂高产率生成 2-氨基嘧啶衍生物、反应时间短、产品分离过程简单等优点。

  DOI：

  10.1007/s13738-012-0189-x

文献信息

• A Novel and Efficient One-Pot Synthesis of 2-Aminopyrimidinones and Their Self-Assembly
  作者：Morteza Bararjanian、Saeed Balalaie、Frank Rominger、Sanaz Barouti

  DOI：10.1002/hlca.200900319

  日期：2010.4

  A three‐component reaction of benzaldehyde derivatives, methyl cyanoacetate, and guanidinium carbonate affords 2‐amino‐4‐aryl‐1,6‐dihydro‐6‐oxopyrimidine‐5‐carbonitriles and the four‐component reaction of benzaldehyde derivatives, methyl cyanoacetate, and guanidinium hydrochloride in the presence of piperidine leads to piperidinium salts of pyrimidinones. X‐ray crystallography data confirm self‐assembly

  苯甲醛衍生物，氰基乙酸甲酯和碳酸胍的三组分反应得到2-氨基-4-芳基-1,6-二氢-6-氧嘧啶-5-腈和苯甲醛衍生物，氰基乙酸甲酯的四组分反应，在哌啶存在下，盐酸胍盐会生成嘧啶酮的哌啶鎓盐。X射线晶体学数据证实了这些化合物的自组装和氢键作用。
• A novel and efficient one step synthesis of 2-amino-5-cyano-6-hydroxy-4-aryl pyrimidines and their anti-bacterial activity
  作者：M.B. Deshmukh、S.M. Salunkhe、D.R. Patil、P.V. Anbhule

  DOI：10.1016/j.ejmech.2008.10.018

  日期：2009.6

  The first simple and efficient approach towards one step synthesis of 2-amino-5-cyano-6-hydroxy-4-aryl pyrimidines has been developed by three component condensation of aromatic aldehydes, ethyl cyanoacetate and guanidine hydrochloride in alkaline ethanol. The synthesized compounds evaluated for their anti-bacterial activity against Gram-positive and Gram-negative bacteria. The some of the compounds

  通过在碱性乙醇中芳族醛，氰基乙酸乙酯和盐酸胍的三组分缩合，已经开发出第一种简单有效的一步合成2-氨基-5-氰基-6-羟基-4-芳基嘧啶的方法。评估了合成化合物对革兰氏阳性和革兰氏阴性细菌的抗菌活性。一些化合物对被测细菌表现出优异的抑制作用。
• Fullerene‐ <scp> C ₆₀ </scp> / <scp> NH ₂ </scp> : A recyclable heterogeneous catalyst for the green synthesis of chromene and pyrimidine derivatives and antibacterial evaluation
  作者：Maryam Mirza‐Aghayan、Marzieh Mohammadi、Rabah Boukherroub

  DOI：10.1002/jhet.4453

  日期：2022.6

  procedure environmentally benign. Antibacterial behavior of some of the synthesized products was studied against Gram-positive and Gram-negative bacteria using disk and well diffusion methods. The chromene 4g showed a good antibacterial activity against both bacterial strains Staphylococcus aureus and Serratia marcescens. A good antibacterial activity was also detected for chromene 4o and pyrimidine 7j against

  描述了一种用二亚乙基三胺 (C 60 -NH 2 )合成氨基官能化富勒烯的有效方法。所获得的材料通过傅里叶变换红外光谱、X 射线衍射、扫描电子显微镜、能量色散 X 射线光谱、元素分析、热重测量和 X 射线光电子能谱进行表征。研究了C 60 -NH 2在合成色烯和嘧啶衍生物的多组分反应中的催化活性。结果表明，C 60 -NH 2是非常有效的，所需的色烯和嘧啶产物的分离率分别为 78%–97% 和 81%–98%。此外，C 60 -NH 2催化剂可以回收和再利用至少八次运行而不会显着降低其活性，这使得我们的程序对环境无害。使用圆盘和孔扩散方法研究了一些合成产物对革兰氏阳性和革兰氏阴性细菌的抗菌行为。色烯4g对金黄色葡萄球菌和粘质沙雷氏菌均表现出良好的抗菌活性。还检测到色烯4o和嘧啶具有良好的抗菌活性7j抗金黄色葡萄球菌。色烯4m、4n和嘧啶7i化合物对作为革兰氏阳性细菌的Micrococcus
• A spectral deciphering the perturbation of model transporter protein (HSA) by antibacterial pyrimidine derivative: Pharmacokinetic and biophysical insights
  作者：Vishwas D. Suryawanshi、Prashant V. Anbhule、Anil H. Gore、Shivajirao R. Patil、Govind B. Kolekar

  DOI：10.1016/j.jphotobiol.2012.09.010

  日期：2013.1

  Steady state fluorescence and UV-vis absorption spectroscopic techniques have been exploited to explore the binding interaction of a antibacterial pyrimidine derivative 2-amino-6-hydroxy-4-(4-hydroxy-phenyl)-pyrimidine-5-carbonitrile (AHHPPC) with the model transporter protein, human serum albumin (HSA) under the physiological conditions. It exhibits antibacterial activity against Escherichia coli and Staphylococcus aureus. Analysis of fluorescence quenching data of HSA at different temperatures using Stern-Volmer methods revealed the formation of AHHPPC-HSA complex with binding affinities of the order 10(4) M-1. The binding site number (n approximate to 1) and corresponding thermodynamic parameters (Delta G), (Delta H) and (Delta S) were calculated, indicated that binding reaction was endothermic and the hydrophobic interactions plays a major role in stabilizing the complex. The binding distance (r approximate to 3.13 nm) between donor (HSA) and acceptor (AHHPPC) was obtained according to FRET. Changes in the albumin secondary structure imparted by the compound was confirmed using synchronous fluorescence, electronic absorption, circular dichroism (CD) and three-dimensional (3D) fluorescence spectroscopy. All these experimental results clarified that AHHPPC could bind to HSA and be effectively transported and eliminated in body, which could be a useful guideline for further drug design. (C) 2012 Elsevier B.V. All rights reserved.