1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-oxopyrimidine-5-carboxylic acid | 1185854-71-0

• 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: 1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-oxopyrimidine-5-carboxylic acid
• 英文别名: 1,2,3,4-tetrahydro-6-methyl-2-oxo-4-(2-hydroxyphenyl)-pyrimidine-5-carboxylic acid；4-(2-hydroxyphenyl)-6-methyl-2-oxo-3,4-dihydro-1H-pyrimidine-5-carboxylic acid
• CAS: 1185854-71-0
• 化学式: C₁₂H₁₂N₂O₄
• 分子量: 248.238
• InChiKey: YVKOAZDUXZBJPY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  98.7
• 氢给体数：
  4
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-oxopyrimidine-5-carboxylic acid 在 2-(1H-benzotriazol-1-yl)-1,1,3,3-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.33h， 以87%的产率得到4-methyl-1H-chromeno[4,3-d]pyrimidine-2,5(3H,10bH)-dione
  参考文献：
  名称：

  Synthesis of fused dihydro-pyrimido[4,3-d]coumarins using Biginelli multicomponent reaction as key step

  摘要：

  A new efficient approach for the synthesis of functionalized dihydro-pyrimido[4,3-d]coumarins is described. Use of benzyl- or tert-butyl acetoacetate and various salicyl aldehydes in typical Biginelli multicomponent reactions provides esters that can be easily deprotected to yield the corresponding hydroxy acids. Annelation of the latter leads to the target dihydro-pyrimido[4,3-d]coumarins. Formation of some unexpected oxo-bridged tetrahydro-pyrimidines is also described. Spectral properties of the synthesized dihydro-pyrimido[4,3-d]coumarins indicate the necessity to revisit some compounds previously reported as products of direct one-pot Biginelli condensation involving 4-hydroxycoumarin as dicarbonyl component. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2009.05.088
• 作为产物：
  描述：

  benzyl 1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-oxopyrimidine-5-carboxylate 在 palladium 10% on activated carbon 、 甲酸铵 作用下， 以 甲醇 为溶剂， 以20%的产率得到1,2,3,4-tetrahydro-4-(2-hydroxyphenyl)-6-methyl-2-oxopyrimidine-5-carboxylic acid
  参考文献：
  名称：

  新型1,2,3,4-四氢嘧啶-5-羧酸衍生物的设计，合成和抗HIV-1评估。

  摘要：

  根据HIV-1 gp41结合位点抑制剂NB-2和NB-64的结构，设计，合成了一系列四氢嘧啶衍生物（2a-2l），并筛选了抗HIV-1特性。进行了一项计算研究，以预测所研究分子的药效动力学，药代动力学和类药物特征。对接研究表明，分子中的羧酸基与Lys574或Arg579形成盐桥。所合成化合物的理化性质（例如分子量，氢键供体的数目，氢键受体的数目和可旋转键的数目）证实并显示出这些化合物在李宾斯基五定律设定的范围内。在四氢嘧啶环的C（4）位置具有4-氯苯基取代基和4-甲基苯基的化合物2e和2k是最有效的化合物之一。这表明这些化合物可作为开发新型小分子HIV-1抑制剂的先导。

  DOI：

  10.1002/cbdv.201700502

文献信息

• [EN] NOVEL 2-OXO-1,2,3,4-TETRAHYDROPYRIMIDINES, BICYCLIC PYRIMIDINE DIONES AND IMIDAZOLIDINE-2,4-DIONES USEFUL AS INDUCIBLE NITRIC OXIDE SYNTHASE INHIBITORS<br/>[FR] NOUVELLES 2-OXO-1,2,3,4-TÉTRAHYDROPYRIMIDINES, PYRIMIDINE DIONES BICYCLIQUES ET IMIDAZOLIDINE-2,4-DIONES UTILES COMME INHIBITEURS DE L'OXYDE NITRIQUE SYNTHASE INDUCTIBLE
  申请人：KALYPSYS INC

  公开号：WO2007101213A2

  公开（公告）日：2007-09-07

  [EN] The present invention relates to novel 2-oxo-l,2,3,4-tetrahydropyrimidines, bicyclic pyrimidine diones and imidizolidine-2,4-diones and methods useful as inhibitors of nitric oxide synthase.
  [FR] La présente invention concerne de nouvelles 2-oxo-1,2,3,4-tétrahydropyrimidines, pyrimidine diones bicycliques et imidizolidine-2,4-diones et des procédés, utiles comme inhibiteurs de l'oxyde nitrique synthase.
• Design, Synthesis, and Anti-HIV-1 Evaluation of a Novel Series of 1,2,3,4-Tetrahydropyrimidine-5-Carboxylic Acid Derivatives
  作者：Saghi Sepehri、Sepehr Soleymani、Rezvan Zabihollahi、Mohammad R. Aghasadeghi、Mehdi Sadat、Lotfollah Saghaie、Hamid R. Memarian、Afshin Fassihi

  DOI：10.1002/cbdv.201700502

  日期：2018.4

  A series of tetrahydropyrimidine derivatives (2a - 2l) were designed, synthesized, and screened for anti-HIV-1 properties based on the structures of HIV-1 gp41 binding site inhibitors, NB-2 and NB-64. A computational study was performed to predict the pharmacodynamics, pharmacokinetics, and drug-likeness features of the studied molecules. Docking studies revealed that the carboxylic acid group in the

  根据HIV-1 gp41结合位点抑制剂NB-2和NB-64的结构，设计，合成了一系列四氢嘧啶衍生物（2a-2l），并筛选了抗HIV-1特性。进行了一项计算研究，以预测所研究分子的药效动力学，药代动力学和类药物特征。对接研究表明，分子中的羧酸基与Lys574或Arg579形成盐桥。所合成化合物的理化性质（例如分子量，氢键供体的数目，氢键受体的数目和可旋转键的数目）证实并显示出这些化合物在李宾斯基五定律设定的范围内。在四氢嘧啶环的C（4）位置具有4-氯苯基取代基和4-甲基苯基的化合物2e和2k是最有效的化合物之一。这表明这些化合物可作为开发新型小分子HIV-1抑制剂的先导。
• Synthesis of fused dihydro-pyrimido[4,3-d]coumarins using Biginelli multicomponent reaction as key step
  作者：Mihaela Matache、Cristian Dobrota、Niculina D. Bogdan、Ioana Dumitru、Lavinia L. Ruta、Codruta C. Paraschivescu、Ileana C. Farcasanu、Ion Baciu、Daniel P. Funeriu

  DOI：10.1016/j.tet.2009.05.088

  日期：2009.8

  A new efficient approach for the synthesis of functionalized dihydro-pyrimido[4,3-d]coumarins is described. Use of benzyl- or tert-butyl acetoacetate and various salicyl aldehydes in typical Biginelli multicomponent reactions provides esters that can be easily deprotected to yield the corresponding hydroxy acids. Annelation of the latter leads to the target dihydro-pyrimido[4,3-d]coumarins. Formation of some unexpected oxo-bridged tetrahydro-pyrimidines is also described. Spectral properties of the synthesized dihydro-pyrimido[4,3-d]coumarins indicate the necessity to revisit some compounds previously reported as products of direct one-pot Biginelli condensation involving 4-hydroxycoumarin as dicarbonyl component. (C) 2009 Elsevier Ltd. All rights reserved.