5-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione | 428444-70-6

• 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: 5-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione
• 英文别名: 5-benzyl-6-methyluracil；5-benzyl-6-methyl-1H-pyrimidine-2,4-dione；5-Benzyl-6-methyl-1H-pyrimidin-2,4-dion；5-benzyl-6-methyl-1H-pyrimidine-2,4-dione
• CAS: 428444-70-6
• 化学式: C₁₂H₁₂N₂O₂
• 分子量: 216.239
• InChiKey: GRUQJQSTHUDUKU-UHFFFAOYSA-N

物化性质

• 熔点：
  221-222 °C
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 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：
  58.2
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  5-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione 、 氯甲基乙醚 在 牛血清白蛋白 作用下， 以 乙腈 为溶剂， 以67%的产率得到1-(ethoxymethyl)-5-benzyl-6-methyluracil
  参考文献：
  名称：

  Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors

  摘要：

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.

  DOI：

  10.1080/00397910600772850
• 作为产物：
  描述：

  6-甲基尿嘧啶 在 palladium on activated charcoal 盐酸 、 barium dihydroxide 、 三甲基氯硅烷 、 氢溴酸 、 甲酸铵 、 sodium hydride 、 溶剂黄146 、 1,2-二溴乙烷 、 锌 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 177.0h， 生成 5-benzyl-6-methylpyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors

  摘要：

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.

  DOI：

  10.1080/00397910600772850

文献信息

• [EN] COMPOSITIONS AND METHODS FOR INHIBITING N-SMASE2<br/>[FR] COMPOSITIONS ET PROCÉDÉS D'INHIBITION DE LA N-SMASE2
  申请人：UNIV CALIFORNIA

  公开号：WO2019055832A1

  公开（公告）日：2019-03-21

  Provided herein are compounds of Formula (I) and (II) and their salts, and compositions comprising such compounds that are useful for useful for modulating neutral sphingomyelinase 2 (n-SMase2) in cells. Also disclosed herein are methods of using the disclosed compounds and compositions for inhibiting the spread of Tau seeds from donor cells to recipient cells. Moreover, disclosed herein are methods of using the disclosed compounds and compositions for treating or preventing a neurodegenerative disorder, such as a tauopathy, Alzheimer's disease (AD), Parkinson's disease (PD), Huntington's disease (HD), Lewy body dementia, frontotemporal dementia, and amyotrophic lateral sclerosis (ALS).

  本文提供了化合物I和II及其盐，以及包含这些化合物的组合物，用于调节细胞中的中性鞘磷脂酰胆碱酰肌醇酶2（n-SMase2）。本文还披露了使用上述化合物和组合物抑制Tau种子从供体细胞传播到受体细胞的方法。此外，本文还披露了使用上述化合物和组合物治疗或预防神经退行性疾病的方法，例如tau病理、阿尔茨海默病（AD）、帕金森病（PD）、亨廷顿病（HD）、Lewy体痴呆、额颞叶痴呆和肌萎缩侧索硬化症（ALS）。
• Synthesis of modified uracil and cytosine nucleobases using a microwave-assisted method
  作者：Laxmi Narayana Burgula、K. Radhakrishnan、Lal Mohan Kundu

  DOI：10.1016/j.tetlet.2012.03.056

  日期：2012.5

  Modified nucleobases and nucleic acids have found many biological and pharmaceutical applications. Here we report a microwave-directed synthesis of a variety of modified uracil and cytosine nucleobases with high yields under solvent-free conditions. The reaction yields were further improved by addition of Lewis acid. The crystal structures of 5-isopropyl-6-methyluracil and 6-phenyluracil were also determined. (C) 2012 Elsevier Ltd. All rights reserved.
• Wheeler; McFarland, American Chemical Journal, 1909, vol. 42, p. 114
  作者：Wheeler、McFarland

  DOI：——

  日期：——
• COMPOSITIONS AND METHODS FOR INHIBITING N-SMASE2
  申请人：BILOUSOVA Tina

  公开号：US20200270216A1

  公开（公告）日：2020-08-27

  Provided herein are compounds of Formula (I) and (II) and their salts, and compositions comprising such compounds that are useful for useful for modulating neutral sphingomyelinase 2 (n-SMase2) in cells. Also disclosed herein are methods of using the disclosed compounds and compositions for inhibiting the spread of Tau seeds from donor cells to recipient cells. Moreover, disclosed herein are methods of using the disclosed compounds and compositions for treating or preventing a neurodegenerative disorder, such as a tauopathy, Alzheimer's disease (AD), Parkinson's disease (PD), Huntington's disease (HD), Lewy body dementia, frontotemporal dementia, and amyotrophic lateral sclerosis (ALS).
• Synthesis of l‐(Alkoxymethyl)‐5‐benzyl‐6‐methyluracil as Potential Nonnucleoside HIV‐1 RT Inhibitors
  作者：Yanli Chen、Ying Guo、Hua Yang、Xiaowei Wang、Junyi Liu

  DOI：10.1080/00397910600772850

  日期：2006.9.1

  1,3-Dibenzyl-6-methyl-5-zincbromomethyluracil 6 was prepared starting from 6-methyluracil 1. The cross-coupling reaction of benzylic zinc reagent 6 with PhI using bis(dibenzylideneacetone) palladium( 0) and (o-furyl)(3)P as catalyst gave 1,3,5-tribenzyl-6-methyluracil 7. The N-1, N-3-dibenzyl group could be removed in dealkylation to give the 5-benzyl-6-methyluracil 8. It was N-1-alkylated with chloromethyl ethyl ether or chloromethyl benzyl ether to obtained the targets 9a and b. All synthesized compounds were tested for their inhibition of HIV-1 reverse transcriptase, and moderate activity were found for target compounds 9a and b and 5.