4-amino-2-mercapto-6-(p-tolyl)pyrimidine-5-carbonitrile | 75129-08-7

• 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-2-mercapto-6-(p-tolyl)pyrimidine-5-carbonitrile
• 英文别名: Pyrimidine-5-carbonitrile, 4-amino-2-mercapto-6-p-tolyl-；4-amino-6-(4-methylphenyl)-2-sulfanylidene-1H-pyrimidine-5-carbonitrile
• CAS: 75129-08-7
• 化学式: C₁₂H₁₀N₄S
• 分子量: 242.304
• InChiKey: VHFGQVKCHHHGJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  106
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-amino-2-mercapto-6-(p-tolyl)pyrimidine-5-carbonitrile 在 双氧水 、 potassium carbonate 作用下， 以 水 为溶剂， 以63%的产率得到4-Amino-2-hydroxy-6-p-tolyl-pyrimidine-5-carbonitrile
  参考文献：
  名称：

  El-Sharabsy, Salwa A.; Gawad, Soad M. Abdel; Hussain, Sohair M., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 2, p. 207 - 211

  摘要：

  DOI：
• 作为产物：
  描述：

  2-(4-甲基亚苄基)-丙二腈 、 硫脲 在 potassium carbonate 作用下， 以 乙醇 为溶剂， 反应 5.0h， 以68%的产率得到4-amino-2-mercapto-6-(p-tolyl)pyrimidine-5-carbonitrile
  参考文献：
  名称：

  El-Sharabsy, Salwa A.; Gawad, Soad M. Abdel; Hussain, Sohair M., Journal fur praktische Chemie (Leipzig 1954), 1989, vol. 331, # 2, p. 207 - 211

  摘要：

  DOI：

文献信息

• One pot synthesis of pyrimidine-5-carbonitrile and pyrimidine-5-carboxamide using ammonium chloride under solvent free condition
  作者：J S Aher、A V kardel、M R Gaware、D D Lokhande、A M Bhagare

  DOI：10.1007/s12039-019-1633-6

  日期：2019.7

  various substituted benzaldehyde, malononitrile and cyanoacetamide, urea/thiourea in the presence of ammonium chloride followed by characterization using IR, \(^1}\hbox H NMR}\) spectroscopic technique. Graphic Abstract Pyrimidine-5-carbonitrile and pyrimidine-5-carboxamide were synthesized from the various substituted benzaldehyde, malononitrile and cyanoacetamide, urea/thiourea in the presence of

  摘要在氯化铵存在下，由各种取代的苯甲醛，丙二腈和氰基乙酰胺，脲/硫脲合成嘧啶-5-甲腈和嘧啶-5-羧酰胺，然后使用IR进行表征，\（^ 1} \ hbox H NMR} \）光谱技术。 图形摘要 在氯化铵的存在下，由各种取代的苯甲醛，丙二腈和氰基乙酰胺，脲/硫脲合成嘧啶-5-腈和嘧啶-5-羧酰胺。
• Tacripyrimidines, the first tacrine-dihydropyrimidine hybrids, as multi-target-directed ligands for Alzheimer's disease
  作者：Mourad Chioua、Eleonora Buzzi、Ignacio Moraleda、Isabel Iriepa、Maciej Maj、Artur Wnorowski、Catia Giovannini、Anna Tramarin、Federica Portali、Lhassane Ismaili、Pilar López-Alvarado、Maria Laura Bolognesi、Krzysztof Jóźwiak、J. Carlos Menéndez、José Marco-Contelles、Manuela Bartolini

  DOI：10.1016/j.ejmech.2018.06.044

  日期：2018.7

  Notwithstanding the combination of cholinesterase (ChE) inhibition and calcium channel blockade within a multitarget therapeutic approach is envisaged as potentially beneficial to confront Alzheimer's disease (AD), this strategy has been scarcely investigated. To explore this promising line, a series of 5-amino-4-aryl-3,4,6,7,8,9-hexahydropyrimido [4,5-b]quinoline-2(1H)-thiones (tacripyrimidines) (4a-l)

  尽管在多靶点治疗方法中胆碱酯酶（ChE）抑制和钙通道阻滞相结合被认为对对抗阿尔茨海默氏病（AD）具有潜在的益处，但几乎没有研究这种策略。为了探索这一有前途的路线，一系列的5-氨基-4-芳基-3,4,6,7,8,9-六氢嘧啶基[4,5-b]喹啉-2（1 H）-硫酮（tacripyrimidines）（通过并置他克林，一种ChE抑制剂（ChEI）和3,4-二氢嘧啶-2（1 H）-硫酮设计了4a - 1）作为有效的钙通道阻滞剂（CCBs）。根据其设计，所有tacripyrimidines，未取代的母体化合物及其p-甲氧基衍生物，起中等至强效CCB的作用，其活性通常与参考CCB药物尼莫地平相似或更高，并且是中等至良好的ChEI。最有趣的是，3'-甲氧基衍生物（4e）作为第一种平衡良好的ChEI / CCB试剂出现，起低微摩尔hChEI（分别在hAChE和hBuChE上分别为3.05μM和3.19μM）和中等CCB（1μM时为30
• 4-Amino-5-Cyanopyrimidine Derivatives
  申请人：Kato Masaya

  公开号：US20080182854A1

  公开（公告）日：2008-07-31

  The present invention provides 4-amino-5-cyanopyrimidine derivatives of the formula: wherein R 1 , R 2 and R 3 are defined herein, or pharmaceutically acceptable salts thereof, having a safe and potent adenosine A2a receptor agonistic activity; and also provides an adenosine A2a receptor agonist, an intraocular pressure reducing agent, or a medicine for treating glaucoma, etc., which comprises the compound as an active ingredient.

  本发明提供了式子如下的4-氨基-5-氰基嘧啶衍生物：其中R1、R2和R3如本文所定义，或其药学上可接受的盐，具有安全有效的腺苷A2a受体激动活性；同时还提供了一种腺苷A2a受体激动剂、降眼压剂或治疗青光眼等药物，其包含该化合物作为活性成分。
• Synthesis and Antimicrobial Activity of Thioxopyrimidines and Related Derivatives
  作者：Ahmed M. El-Agrody、Fawzy M. Ali、Fathy A. Eid、Mohammed A. A. El-Nassag、Gamal El-Sherbeny、Ahmed H. Bedair

  DOI：10.1080/10426500500272087

  日期：2006.4.1

  The interaction of thiourea with activated cyanoolefins under different reaction conditions were studied, in which a variety of thiopyrimidines (8, 9, 12, 18, 20, & 21) and related derivatives (10, 11, 14, 16, & 17) were obtained respectively. Also, the reactions of thiopyrimidines (8, 9) with different electrophilic and nucleophilic reagents were reported. IR, H-1 NMR, C-13 NMR and mass spectra for the newly synthesized compounds were studied. Most of the obtained compounds were screened against Gram-postive and Gram-negative bacteria and fungi, for which some of these derivatives gave promising results.
• Agonists for the Adenosine A₁ Receptor with Tunable Residence Time. A Case for Nonribose 4-Amino-6-aryl-5-cyano-2-thiopyrimidines
  作者：Julien Louvel、Dong Guo、Marta Agliardi、Tamara A. M. Mocking、Roland Kars、Tan Phát Pham、Lizi Xia、Henk de Vries、Johannes Brussee、Laura H. Heitman、Adriaan P. IJzerman

  DOI：10.1021/jm401643m

  日期：2014.4.24

  We report the synthesis and evaluation of previously unreported 4-amino-6-aryl-5-cyano-2-thiopyrimidines as selective human adenosine A(1) receptor (hA(1)AR) agonists with tunable binding kinetics, this without affecting their nanomolar affinity for the target receptor. They show a very diverse range of kinetic profiles (from 1 min (compound 52) to 1 h (compound 43)), and their structure-affinity relationships (SAR) and structure-kinetics relationships (SKR) were established. When put in perspective with the increasing importance of binding kinetics in drug discovery, these results bring new evidence of the consequences of affinity-only driven selection of drug candidates, that is, the potential elimination of slightly less active compounds that may display preferable binding kinetics.