1,3-dimethyl-5-(2,3,4-trimethoxybenzylidene)-hexahydropyrimidine-2,4,6-trione

• 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: 1,3-dimethyl-5-(2,3,4-trimethoxybenzylidene)-hexahydropyrimidine-2,4,6-trione
• 英文别名: 1,3-dimethyl-5-(2,3,4-trimethoxybenzylidene)pyrimidine-2,4,6(1H,3H,5H)-trione；1,3-dimethyl-5-[(2,3,4-trimethoxyphenyl)methylidene]-1,3-diazinane-2,4,6-trione
• 化学式: C₁₆H₁₈N₂O₆
• 分子量: 334.329
• InChiKey: JPPXVMOFTVFVIV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  85.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,3-dimethyl-5-(2,3,4-trimethoxybenzylidene)-hexahydropyrimidine-2,4,6-trione 在 sodium tetrahydroborate 作用下， 以 水 、 异丙醇 为溶剂， 以76%的产率得到1,3-Dimethyl-5-[(2,3,4-trimethoxyphenyl)methyl]-1,3-diazinane-2,4,6-trione
  参考文献：
  名称：

  Chemical modification of plant alkaloids. I. Aminomethylation of barbituric acid derivatives by cytisine

  摘要：

  Reaction of cytisine with 1-mono- and 1,3-disubstituted 5-arylmethylbarbituric acids in the presence of formaldehyde results in aminomethylation of C-5 to form the corresponding 5-cytisylmethylbarbituric acids. The structures of the products are found using PMR spectroscopy mid mass spectrometry. 1-Phenyl-5-(2,4-dimethoxybenzyl)-5-cytisylmethylbarbituric acid is obtained as a mixture of two steroisomers in an approximately 2:1 ratio.

  DOI：

  10.1007/bf02236429
• 作为产物：
  描述：

  1,3-二甲基巴比妥酸 、 2,3,4-三甲氧基苯甲醛 在 苄基三甲基氯化铵 作用下， 以 水 为溶剂， 反应 5.0h， 以96%的产率得到1,3-dimethyl-5-(2,3,4-trimethoxybenzylidene)-hexahydropyrimidine-2,4,6-trione
  参考文献：
  名称：

  与环状砜的狄尔斯-阿尔德反应：VIII。螺[1-苯并噻吩-4,5'-嘧啶] -2'，4'，6'-三酮1,1-二氧化物和2'-噻吩并螺[1-苯并噻吩-4,5'-的有机催化嘧啶] -4′，6′-二酮1,1-二氧化物

  摘要：

  5-异丙烯基-2,3-二氢噻吩1,1-二氧化物在手性胺或氨基酸存在下与5-亚甲基亚嘧啶-2,4,6-三酮和5-亚甲基-2-硫代嘧啶-4,6-二酮反应具有高的区域和立体选择性，可将在5位上稠合的巴比妥酸和硫代巴比妥酸的旋光衍生物衍生为1-苯并噻吩1,1-二氧化物片段。5-异丙烯基-2,3-二氢噻吩1,1-二氧化物与5-（2-甲氧基亚苄基）-2-硫代嘧啶-4,6-二酮（由2-甲氧基苯甲醛和硫代巴比妥酸原位生成）的反应（-）-麻黄碱或L-4-（叔丁基二甲基甲硅烷氧基）脯氨酸的混合物制得相应的2-thioxospiro [1-苯并噻吩-4,5'-嘧啶] -4'，6'-二酮1,1-二氧化物对映体过量80％。

  DOI：

  10.1134/s1070428009010126

文献信息

• Diels-alder reactions with cyclic sulfones: VIII. Organic catalysis in the synthesis of spiro[1-benzothiophene-4,5′-pyrimidine]-2′,4′,6′-trione 1,1-dioxides and 2′-thioxospiro[1-benzothiophene-4,5′-pyrimidine]-4′,6′-dione 1,1-dioxides
  作者：E. E. Shul’ts、G. N. Andreev、M. M. Shakirov、N. I. Komarova、I. Yu. Bagryanskaya、Yu. V. Gatilov、G. A. Tolstikov

  DOI：10.1134/s1070428009010126

  日期：2009.1

  from 2-methoxybenzaldehyde and thiobarbituric acid) in the presence of (−)-ephedrine or L-4-(tert-butyldimethylsiloxy) proline gave the corresponding 2-thioxospiro[1-benzothiophene-4,5′-pyrimidine]-4′,6′-dione 1,1-dioxide with an enantiomeric excess of 80%.

  5-异丙烯基-2,3-二氢噻吩1,1-二氧化物在手性胺或氨基酸存在下与5-亚甲基亚嘧啶-2,4,6-三酮和5-亚甲基-2-硫代嘧啶-4,6-二酮反应具有高的区域和立体选择性，可将在5位上稠合的巴比妥酸和硫代巴比妥酸的旋光衍生物衍生为1-苯并噻吩1,1-二氧化物片段。5-异丙烯基-2,3-二氢噻吩1,1-二氧化物与5-（2-甲氧基亚苄基）-2-硫代嘧啶-4,6-二酮（由2-甲氧基苯甲醛和硫代巴比妥酸原位生成）的反应（-）-麻黄碱或L-4-（叔丁基二甲基甲硅烷氧基）脯氨酸的混合物制得相应的2-thioxospiro [1-苯并噻吩-4,5'-嘧啶] -4'，6'-二酮1,1-二氧化物对映体过量80％。
• Synthesis and antifungal activity of substituted 2,4,6-pyrimidinetrione carbaldehyde hydrazones
  作者：Donna M. Neumann、Amy Cammarata、Gregory Backes、Glen E. Palmer、Branko S. Jursic

  DOI：10.1016/j.bmc.2013.12.010

  日期：2014.1

  Opportunistic fungal infections caused by the Candida spp. are the most common human fungal infections, often resulting in severe systemic infections-a significant cause of morbidity and mortality in at-risk populations. Azole antifungals remain the mainstay of antifungal treatment for candidiasis, however development of clinical resistance to azoles by Candida spp. limits the drugs' efficacy and highlights the need for discovery of novel therapeutics. Recently, it has been reported that simple hydrazone derivatives have the capability to potentiate antifungal activities in vitro. Similarly, pyrimidinetrione analogs have long been explored by medicinal chemists as potential therapeutics, with more recent focus being on the potential for pyrimidinetrione antimicrobial activity. In this work, we present the synthesis of a class of novel hydrazone-pyrimidinetrione analogs using novel synthetic procedures. In addition, structure-activity relationship studies focusing on fungal growth inhibition were also performed against two clinically significant fungal pathogens. A number of derivatives, including phenylhydrazones of 5-acylpyrimidinetrione exhibited potent growth inhibition at or below 10 mu M with minimal mammalian cell toxicity. In addition, in vitro studies aimed at defining the mechanism of action of the most active analogs provide preliminary evidence that these compound decrease energy production and fungal cell respiration, making this class of analogs promising novel therapies, as they target pathways not targeted by currently available antifungals. (C) 2013 Elsevier Ltd. All rights reserved.
• Chemical modification of plant alkaloids. I. Aminomethylation of barbituric acid derivatives by cytisine
  作者：K. A. Krasnov、V. G. Kartsev、A. S. Gorovoi

  DOI：10.1007/bf02236429

  日期：2000.3

  Reaction of cytisine with 1-mono- and 1,3-disubstituted 5-arylmethylbarbituric acids in the presence of formaldehyde results in aminomethylation of C-5 to form the corresponding 5-cytisylmethylbarbituric acids. The structures of the products are found using PMR spectroscopy mid mass spectrometry. 1-Phenyl-5-(2,4-dimethoxybenzyl)-5-cytisylmethylbarbituric acid is obtained as a mixture of two steroisomers in an approximately 2:1 ratio.