4-N-(5-hydroxymethylfurfuryl)cytosine | 1333466-51-5

• 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: 4-N-(5-hydroxymethylfurfuryl)cytosine
• 英文别名: 4-N-(5-hydroxymethyI)furfurylcytosine；4-(((5-(hydroxymethyl)furan-2-yl)methyl)amino)pyrimidin-2(1H)-one；6-[[5-(hydroxymethyl)furan-2-yl]methylamino]-1H-pyrimidin-2-one
• CAS: 1333466-51-5
• 化学式: C₁₀H₁₁N₃O₃
• 分子量: 221.216
• InChiKey: PHBJRSFXAFRHDC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  86.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-羟甲基糠醛 在 sodium tetrahydroborate 、 magnesium methanolate 作用下， 以 甲醇 为溶剂， 反应 3.5h， 生成 4-N-(5-hydroxymethylfurfuryl)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

• CYTOSINE ANALOGUE, A METHOD OF PREPARATION OF A CYTOSINE ANALOGUE, A DNA METHYLTRANSFERASE 1 INHIBITOR, A METHOD FOR DNA METHYLATION INHIBITION, THE USE OF THE ANALOGUE IN THE TREATMENT OF DISEASES ASSOCIATED WITH DEVIATIONS FROM NORMAL DNA METHYLATION
  申请人：Barciszewski Jan

  公开号：US20120322755A1

  公开（公告）日：2012-12-20

  This invention provides a cytosine analogue, a method of preparation of a cytosine analogue, a DNA rhethyltransferase 1 inhibitor, a method for DNA methylation inhibition, the use of the analogue in the treatment of diseases associated with deviations from normal DNA methylation. More precisely, the invention relates to various derivatives of cytosine, as well as methods of preparation of mono- and multi-1,4,5 and 6-substituted cytosines. In general, the solution relates to providing effective modulators of DNA methylation which could be used in prevention and treatment of diseases associated with DNA methylation level disorders.

  这项发明提供了一种胞嘧啶类似物，一种制备胞嘧啶类似物的方法，一种DNA甲基转移酶1抑制剂，一种DNA甲基化抑制方法，以及在治疗与正常DNA甲基化偏差相关的疾病中使用该类似物。更具体地说，该发明涉及胞嘧啶的各种衍生物，以及单取代和多1,4,5和6位取代胞嘧啶的制备方法。总的来说，该解决方案涉及提供有效的DNA甲基化调节剂，可用于预防和治疗与DNA甲基化水平紊乱相关的疾病。
• A CYTOSINE ANALOGUE, A METHOD OF PREPARATION OF A CYTOSINE ANALOGUE, A DNA METHYLTRANSFERASE 1 INHIBITOR, A METHOD FOR DNA METHYLATION INHIBITION, THE USE OF THE ANALOGUE IN THE TREATMENT OF DISEASES ASSOCIATED WITH DEVIATIONS FROM NORMAL DNA METHYLATION
  申请人：Instytut Chemii Bioorganicznej PAN

  公开号：EP2556081B1

  公开（公告）日：2021-06-16
• US9040490B2
  申请人：——

  公开号：US9040490B2

  公开（公告）日：2015-05-26
• 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.