4-N-(benzyl-5-methyl)cytosine | 89399-87-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4-N-(benzyl-5-methyl)cytosine
• 英文别名: N⁴-benzyl-5-methylcytosine；6-(benzylamino)-5-methyl-1H-pyrimidin-2-one
• CAS: 89399-87-1
• 化学式: C₁₂H₁₃N₃O
• 分子量: 215.255
• InChiKey: QBFUKKFEXBNTJX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  53.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-benzyl-5-methyl-2’-deoxycytidine 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 4.0h， 以74%的产率得到4-N-(benzyl-5-methyl)cytosine
  参考文献：
  名称：

  New cytosine derivatives as inhibitors of DNA methylation

  摘要：

  DNA cytosine methylation catalyzed by DNA methyltransferase 1 (DNMT1) is an epigenetic method of gene expression regulation and development. Changes in methylation pattern lead to carcinogenesis. Inhibition of DNMT1 activity could be a good strategy of safe and efficient epigenetic therapy. In this work, we present a novel group of cytosine analogs as inhibitors of DNA methylation. We show new methods of synthesis and their effect on in vitro reaction of DNA methylation. Almost all of analyzed compounds inhibit DNA methyltransferase activity in the competitive manner. K-i values for the most potent compound 4-N-furfuryl-5,6-dihydroazacytosines is 0.7 mu M. These compounds cause also a decrease of 5-methylcytosine (m(5)C) level in DNA of mammalian HeLa and HEK293 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2012.07.024

文献信息

• Identification of Chemical Probes Targeting MBD2
  作者：Diane Erdmann、Jean Contreras、Rémy A. Le Meur、Bruno Vitorge、Vincent Saverat、Ambre Tafit、Corinne Jallet、Véronique Cadet-Daniel、Corentin Bon、Phannarath Phansavath、Virginie Ratovelomanana-Vidal、Albert Jeltsch、Sophie Vichier-Guerre、J. Iñaki Guijarro、Paola B. Arimondo

  DOI：10.1021/acschembio.1c00959

  日期：2022.6.17
• New cytosine derivatives as inhibitors of DNA methylation
  作者：Beata Plitta、Ewelina Adamska、Małgorzata Giel-Pietraszuk、Agnieszka Fedoruk-Wyszomirska、Mirosława Naskręt-Barciszewska、Wojciech T. Markiewicz、Jan Barciszewski

  DOI：10.1016/j.ejmech.2012.07.024

  日期：2012.9

  DNA cytosine methylation catalyzed by DNA methyltransferase 1 (DNMT1) is an epigenetic method of gene expression regulation and development. Changes in methylation pattern lead to carcinogenesis. Inhibition of DNMT1 activity could be a good strategy of safe and efficient epigenetic therapy. In this work, we present a novel group of cytosine analogs as inhibitors of DNA methylation. We show new methods of synthesis and their effect on in vitro reaction of DNA methylation. Almost all of analyzed compounds inhibit DNA methyltransferase activity in the competitive manner. K-i values for the most potent compound 4-N-furfuryl-5,6-dihydroazacytosines is 0.7 mu M. These compounds cause also a decrease of 5-methylcytosine (m(5)C) level in DNA of mammalian HeLa and HEK293 cells. (C) 2012 Elsevier Masson SAS. All rights reserved.