6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde | 139958-85-3

• 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: 6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
• 英文别名: 1,3-dimethyl-5-formyl-6-hydroxyuracil；N,N-dimethyl-5-formyl-6-hydroxyuracil；5-formyl-1,3-dimethylbarbituric acid；N,N-dimethyl-5-formylbarbituric acid；4-Hydroxy-1,3-dimethyl-2,6-dioxopyrimidine-5-carbaldehyde
• CAS: 139958-85-3
• 化学式: C₇H₈N₂O₄
• 分子量: 184.152
• InChiKey: QNLODLSTPLTSPI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  77.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-氨基对苯二甲酸 、 6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde 以 甲醇 为溶剂， 以75%的产率得到2-((tetrahydro-1,3-dimethyl-2,4,6-trioxopyrimidin-5(6H)ylidene)methyl)amino-benzene-1,4-dioic acid
  参考文献：
  名称：

  Synthesis of highly functionalized barbituric acids and study of their interactions with p-glycoprotein and Mg2+ – Potential candidates for multi drug resistance modulation

  摘要：

  A number of barbituric acids with appropriate substituent at C-5 position were synthesized and investigated for their interactions with p-gp and Mg2+. Compounds 5, 6, 8-10, 12-14 and 16 increased the basal activity of p-gp by more than 50% at 0.05 mu M concentration. Molecular docking indicate a number of H-bond interactions between these molecules and the amino acid residues of ATP binding site of p-gp. These molecules also showed appreciable interactions with Mg2+, an important component of efflux pump. All the results of these investigations favor the suitability of barbituric acids toward MDR modulation. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.033
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 氯仿 在 potassium hydroxide 、 水 作用下， 以 乙醇 为溶剂， 生成 6-hydroxy-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidine-5-carbaldehyde
  参考文献：
  名称：

  Synthesis of highly functionalized barbituric acids and study of their interactions with p-glycoprotein and Mg2+ – Potential candidates for multi drug resistance modulation

  摘要：

  A number of barbituric acids with appropriate substituent at C-5 position were synthesized and investigated for their interactions with p-gp and Mg2+. Compounds 5, 6, 8-10, 12-14 and 16 increased the basal activity of p-gp by more than 50% at 0.05 mu M concentration. Molecular docking indicate a number of H-bond interactions between these molecules and the amino acid residues of ATP binding site of p-gp. These molecules also showed appreciable interactions with Mg2+, an important component of efflux pump. All the results of these investigations favor the suitability of barbituric acids toward MDR modulation. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.12.033

文献信息

• Studies on uracils: a facile one-pot synthesis of oxazino[4,5-d]-, pyrano[2,3-d]-, pyrido[2,3-d]- and pyrimido[4,5-d]pyrimidines using microwave irradiation in the solid state
  作者：Ipsita Devi、Harsha N Borah、Pulak J Bhuyan

  DOI：10.1016/j.tetlet.2004.01.094

  日期：2004.3

  N,N-Dimethyl-5-formylbarbituric acid 1 reacts with maleimide 2 and phenyl isocyanate/phenyl isothiocyanate 4 under microwave-assisted conditions in the solid phase to afford pyrano[2,3-d]pyrimidines 3 and oxazino[4,5-d]pyrimidines 5 in excellent yields. Under identical conditions, N,N-dimethyl-6-amino-5-formyluracil 6 reacts with 2 and 4 to give pyrido[2,3-d]pyrimidine derivative 7 and pyrimido[4,5-d]pyrimidines

  N，N-二甲基-5-甲酰基巴比妥酸1在固相中微波辅助条件下与马来酰亚胺2和异氰酸苯基酯/异硫氰酸苯基酯4反应，得到吡喃并[2,3- d ]嘧啶3和恶嗪[4,5-]。d ]嘧啶5的收率极好。在相同条件下，N，N-二甲基-6-氨基-5-甲酰基尿嘧啶6与2和4反应生成吡啶并[2,3- d ]嘧啶衍生物7和嘧啶并[4,5- d ]嘧啶8高产。
• A Mild and Efficient Method for the Deformylation of 5-Formyl Uracils and Synthesis of 4,4′-Methylidenebis(1-phenyl-3-methyl-5-pyrazolone)
  作者：Pulak Bhuyan、Mohit Deb、Swarup Majumder

  DOI：10.1055/s-0029-1217536

  日期：2009.7

  6-Substituted 5-formyl uracils undergo an interesting reaction with 1-phenyl-3-methyl-5-pyrazolone in the presence of base catalyst to afford deformylated uracils and 4,4′-methylidenebis(1-phenyl-3-methyl-5-pyrazolone) in excellent yields.

  6-取代的 5-甲酰基尿嘧啶在碱性催化剂存在下与 1-苯基-3-甲基-5-吡唑啉酮发生有趣的反应，得到去甲酰基尿嘧啶和 4,4'-亚甲基双(1-苯基-3-甲基-5) -吡唑啉酮），收率极佳。
• Synthesis of Novel Classes of Pyrido[2,3‐<i>d</i>]‐pyrimidines, Pyrano[2,3‐<i>d</i>]pyrimidines, and Pteridines
  作者：Mohit Lal Deb、Pulak J. Bhuyan

  DOI：10.1080/00397910600775622

  日期：2006.10

  6-Amino-5-formyluracils 1 and 5-formyl-6-hydroxyuracils 4 react with Meldrum's acid 2 in the presence of piperidine as catalyst under thermolytic conditions to afford 6-carboxy-2,4,7-trioxopyrido[2,3-d] pyrimidines 3 and 6-carboxy-2,4,7-trioxopyrano[ 2,3-d] pyrimidines 5 in good yield. Under identical conditions, 6-amino-5- nitrosouracils 6 react with 2 to afford pteridine-6-carboxylic acids 7 in good yields.
• Matyus, Peter; Nieger, Martin; Wamhoff, Heinrich, Phosphorus, Sulfur and Silicon and the Related Elements, 1991, vol. 63, # 3/4, p. 323 - 328
  作者：Matyus, Peter、Nieger, Martin、Wamhoff, Heinrich

  DOI：——

  日期：——
• Singh, Palwinder; Kaur, Jatinder; Paul, Kamaldeep, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2008, vol. 47, # 2, p. 291 - 296
  作者：Singh, Palwinder、Kaur, Jatinder、Paul, Kamaldeep

  DOI：——

  日期：——