N⁴-furfuryl-2'-deoxycytidine | 271790-76-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: N⁴-furfuryl-2'-deoxycytidine
• 英文别名: 4-N-furfuryl-2'-deoxycytidine；4-(furan-2-ylmethylamino)-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
• CAS: 271790-76-2
• 化学式: C₁₄H₁₇N₃O₅
• 分子量: 307.306
• InChiKey: IPAHXSYYUYRPBD-DMDPSCGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.8
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N⁴-furfuryl-2'-deoxycytidine 在 盐酸 、 三乙胺 作用下， 以 甲醇 、 水 为溶剂， 反应 21.0h， 生成 4-N-furfuryl-5-hydroxymethylcytosine
  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
• 作为产物：
  描述：

  在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 N⁴-furfuryl-2'-deoxycytidine
  参考文献：
  名称：

  N（6）-和N（4）-取代的腺嘌呤和胞嘧啶及其2'-脱氧核糖苷的便捷合成方法。

  摘要：

  开发了一种便捷高效的合成腺嘌呤和胞嘧啶的N 6-和N 4-取代衍生物及其2'-脱氧核糖苷的方法。未保护的核碱基（腺嘌呤，胞嘧啶）或未保护的2'-脱氧核糖苷与芳基或烷基醛的反应可生成相应的席夫碱，这些席夫碱可被还原为目标标题化合物，且总收率高。在芳基醛的情况下，亚胺衍生物在甲醇中的甲醇盐存在下获得，并用硼氢化钠还原。与烷基醛的相应反应需要使用乙酸和硼烷二甲基硫醚络合物。

  DOI：

  10.1080/15257770.2012.742198

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。
• METHOD OF OBTAINING OF 4-N-FURFURYLCYTOSINE AND/OR ITS DERIVATIVES, AN ANTI-AGING COMPOSITION AND USE OF 4-N-FURFURYLCYTOSINE AND/OR ITS DERIVATIVES IN THE MANUFACTURE OF ANTI-AGING COMPOSITION
  申请人：Barciszewski Jan

  公开号：US20100317612A1

  公开（公告）日：2010-12-16

  The subjects of the present invention are the method of preparation of 4-furfurylcytosine and/or its derivatives, its use in the manufacture of anti-aging compositions and an anti-aging composition. As 4-furfurylcytosine and/or its derivatives possesses a series of biological properties it might be use as a composition having excellent anti-aging effect to prevent the sagging of skin and loss of luster and to improve sufficiently its aesthetic appearance without significantly change the growth rate and the total growth ability of the skin. Optimal methods of manufacturing this compound, while at the same time obtaining the highest possible process efficiency, with particular emphasis on its utility in the pharmaceutical and cosmetic industries are presented.

  本发明的主题是制备4-糠基胞嘧啶和/或其衍生物的方法，其用于制造抗衰老组合物和一种抗衰老组合物。由于4-糠基胞嘧啶和/或其衍生物具有一系列生物特性，因此它可能被用作具有出色抗衰老效果的组合物，以防止皮肤松弛和光泽丧失，并充分改善其美观外观，而不会显着改变皮肤的生长速率和总生长能力。本文介绍了制造这种化合物的最佳方法，同时获得最高的工艺效率，特别强调其在制药和化妆品行业中的实用性。
• THE SYNTHESIS OF DIENE-CONTAINING NUCLEOSIDE PHOSPHORAMIDITES AND THEIR USE IN THE LABELING OF OLIGONUCLEOTIDES
  作者：Emma Anderson、Douglas Picken

  DOI：10.1081/ncn-200060085

  日期：2005.4.1

  A variety of furan-modified nucleoside phosphoramidite monomers has been prepared and efficiently incorporated into oligonucleotides. These take part in Diels-Alder reactions with fluorescent maleimides to give fluorescent-labeled oligonucleotides. This represents a strategy for oligonucleotide labeling that is orthogonal to amine-based methods.
• [EN] METHOD OF OBTAINING OF 4-N-FURFURYLCYTOSINE AND/OR ITS DERIVATIVES, AN ANTI-AGING COMPOSITION AND USE OF 4-N-FURFURYLCYTOSINE AND/OR ITS DERIVATIVES IN THE MANUFACTURE OF ANTI-AGING COMPOSITION<br/>[FR] PROCÉDÉ D'OBTENTION DE 4-FURFURYLCYTOSINE ET/OU DE SES DÉRIVÉS, COMPOSITION ANTIVIEILLISSEMENT ET UTILISATION DE LA 4-FURFURYLCYTOSINE ET/OU DE SES DÉRIVÉS DANS LA FABRICATION D'UNE COMPOSITION ANTIVIEILLISSEMENT
  申请人：INST CHEMII BIOORG PAN

  公开号：WO2009067035A3

  公开（公告）日：2009-09-24
• 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