4-N-p-toluenesulfonyl-2'-deoxycytidine | 137213-26-4

• 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: 4-N-p-toluenesulfonyl-2'-deoxycytidine
• 英文别名: N-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl]-4-methylbenzenesulfonamide
• CAS: 137213-26-4
• 化学式: C₁₆H₁₉N₃O₆S
• 分子量: 381.409
• InChiKey: FDVHBDMMKDZQFF-GZBFAFLISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  137
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-N-p-toluenesulfonyl-2'-deoxycytidine 在 吡啶 作用下， 生成 N⁴-(2-aminoethyl)-5'-O-(4,4'-dimethoxytrityl)-2'-deoxycytidine
  参考文献：
  名称：

  Phototriggering of Caged Fluorescent Oligodeoxynucleotides

  摘要：

  We describe a synthetic route for incorporating a photocleavable (PC) DABSYL moiety and fluorescein at adjacent cytidines in the middle of a 25-mer oligodeoxynucleotide. In hybridization studies, both fluorescein and the photocleavable DABSYL reduced the T-m about 6 degreesC separately. UV irradiation (355 nm, 2 min) removed the PC-DABSYL moiety, which increased the fluorescence intensity 51-fold and restored the melting temperature. Caged fluorescent oligodeoxynucleotides (CFOs) will allow many DNA processes to be controlled with light.

  DOI：

  10.1021/ol047729n
• 作为产物：
  描述：

  N-{1-[(2R,4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-4-methyl-benzenesulfonamide 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以99%的产率得到4-N-p-toluenesulfonyl-2'-deoxycytidine
  参考文献：
  名称：

  Phototriggering of Caged Fluorescent Oligodeoxynucleotides

  摘要：

  We describe a synthetic route for incorporating a photocleavable (PC) DABSYL moiety and fluorescein at adjacent cytidines in the middle of a 25-mer oligodeoxynucleotide. In hybridization studies, both fluorescein and the photocleavable DABSYL reduced the T-m about 6 degreesC separately. UV irradiation (355 nm, 2 min) removed the PC-DABSYL moiety, which increased the fluorescence intensity 51-fold and restored the melting temperature. Caged fluorescent oligodeoxynucleotides (CFOs) will allow many DNA processes to be controlled with light.

  DOI：

  10.1021/ol047729n

文献信息

• Functionalized carrier materials for the simultaneous synthesis and
  申请人：Boehringer Mannheim GmbH

  公开号：US05574141A1

  公开（公告）日：1996-11-12

  The synthesis and use of polymeric carriers is described which are loaded with nucleic acid building blocks which in turn contain labelling groups or precursors thereof. The polymeric carrier loaded in this way serves as a solid or liquid phase for the assembly of oligonucleotides which can be used as primers for template-dependent enzymatic nucleic acid syntheses such as for example in sequencing analysis according to Sanger and co-workers or in the polymerase chain reaction (PCR).

  本文描述了合成和使用聚合物载体，其装载有含有标记基团或其前体的核酸构建块。以这种方式装载的聚合物载体可作为寡核苷酸的固体或液体相，用于组装寡核苷酸，可用作模板依赖性酶催化核酸合成的引物，例如在Sanger和同事的测序分析中或在聚合酶链反应（PCR）中。
• 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：US08404660B2

  公开（公告）日：2013-03-26

  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4-呋喃基胞嘧啶及其衍生物的制备方法，其在制造抗衰老组合物和抗衰老组合物方面的应用。由于4-呋喃基胞嘧啶及其衍生物具有一系列生物特性，因此可以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，而不显著改变皮肤的生长速率和总生长能力。本发明提供了制造该化合物的最佳方法，同时在制药和化妆品行业中的实用性得到了特别强调，以获得尽可能高的工艺效率。
• 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。
• 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.
• [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