2′-deoxycitidine | 2641-80-7

• 分子结构分类: 有机化合物
• 英文名称: 2′-deoxycitidine
• 英文别名: DHdC；dDHU；4-amino-1-(β-D-erythro-2-deoxy-pentofuranosyl)-5,6-dihydro-1H-pyrimidin-2-one；4-Amino-1-(β-D-erythro-2-desoxy-pentofuranosyl)-5,6-dihydro-1H-pyrimidin-2-on；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-imino-1,3-diazinan-2-one
• CAS: 2641-80-7
• 化学式: C₉H₁₅N₃O₄
• 分子量: 229.236
• InChiKey: DOCREZYYOZBCIN-SHYZEUOFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  108
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2′-deoxycitidine 、 水 生成 alkaline earth salt of/the/ methylsulfuric acid
  参考文献：
  名称：

  Green; Cohen, Journal of Biological Chemistry, 1957, vol. 228, p. 601,605,606

  摘要：

  DOI：
• 作为产物：
  描述：

  2'-脱氧胞嘧啶核苷 在 5% rhodium on activated aluminium oxide 、 氢气 作用下， 以 甲醇 为溶剂， 以32.1 mg的产率得到2′-deoxycitidine
  参考文献：
  名称：

  USES OF DIHYDRO BASES

  摘要：

  本发明提供了含有本文描述的二氢基（例如，化合物DHdC）的药物组合物。该二氢基可能显示多重互变异构体，并可能增加病毒或癌细胞的RNA和/或DNA的突变。该二氢基可用于减少DNA甲基化（例如，在癌细胞中）。本发明还提供包括创新药物组合物的试剂盒和使用这些药物组合物或试剂盒治疗病毒感染（例如流感、HIV感染或丙型肝炎）或癌症的方法。

  公开号：

  US20140206639A1

文献信息

• Laland et al., Acta Chemica Scandinavica (1947), 1957, vol. 11, p. 1081
  作者：Laland et al.

  DOI：——

  日期：——
• Effects of human sulfotransferases on the cytotoxicity of 12-hydroxynevirapine
  作者：Jia-Long Fang、Lucie Loukotková、Priyanka Chitranshi、Gonçalo Gamboa da Costa、Frederick A. Beland

  DOI：10.1016/j.bcp.2018.07.016

  日期：2018.9

  Nevirapine, a non-nucleoside reverse transcriptase inhibitor used for the treatment of AIDS, can cause serious skin rashes and hepatotoxicity. Previous studies have indicated that the benzylic sulfate 12-sulfoxynevirapine, the formation of which is catalyzed by human sulfotransferases (SULTs), may play a causative role in these toxicities. To characterize better the role of 12-sulfoxynevirapine in nevirapine-induced cytotoxicity, the ability of 12 expressed human SULT isoforms to conjugate 12-hydroxynevirapine was assessed. Of the 12 human SULTs, no detectable 12-sulfoxynevirapine was observed with SULT1A3, SULT1C2, SULT1C3, SULT2B1, SULT4A1, or SULT6B1. As determined by the V-max/K-m ratio, SULT2A1 had the highest overall 12-hydoxynevirapine sulfonation activity; lower activities were observed with SULT1A1, SULT1A2, SULT1B1, SULT1C4, and SULT1E1. Incubation of 12-sulfoxynevirapine with glutathione and cysteine led to adduct formation; lower yields were obtained with deoxynucleosides. 12-Hydroxynevirapine was more cytotoxic than nevirapine to TK6, TK6/SULT vector, and TK6/SULT2A1 cells. With nevirapine, there was no difference in cytotoxicity among the three cell lines, whereas with 12-hydroxynevirapine, TK6/SULT2A1 cells were more resistant than TK6 and TK6/SULT vector cells. Co-incubation of 12-hydroxynevirapine with the competitive SULT2A1 substrate dehydroepiandrosterone decreased the level of 12-sulfoxynevirapine and increased the cytotoxicity in TK6/SULT2A1 cells. These data demonstrate that although 12-sulfoxynevirapine reacts with nucleophiles to form adducts, sulfonation of 12-hydroxynevirapine decreases the cytotoxicity of 12-hydroxynevirapine in TK6 cells.
• METHODS OF SCREENING FOR NUCLEOSIDE ANALOGS THAT ARE INCORPORATED BY HIV REVERSE TRANSCRIPTASE AND CAUSE INCORRECT BASE PAIRING
  申请人：DARWIN MOLECULAR CORPORATION

  公开号：EP0767842A1

  公开（公告）日：1997-04-16
• [EN] METHODS OF SCREENING FOR NUCLEOSIDE ANALOGS THAT ARE INCORPORATED BY HIV REVERSE TRANSCRIPTASE AND CAUSE INCORRECT BASE PAIRING<br/>[FR] PROCEDES DE CRIBLAGE D'ANALOGUES DE NUCLEOSIDES INCORPORES PAR LA TRANSCRIPTASE INVERSE DU VIH ET PROVOQUANT UN APPARIEMENT INCORRECT ENTRE BASES
  申请人：LOEB, Lawrence, A.

  公开号：WO1996000797A1

  公开（公告）日：1996-01-11

  (EN) Methods and compositions related to HIV are disclosed. Using the methods of the present invention, nucleoside analogs may be screened for the ability to be incorporated by reverse transcriptase of human immunodeficiency virus ('HIV RT') and cause incorrect base pairing. Progressive mutation of the virus by such nucleoside analogs renders it non-viable.(FR) L'invention concerne des procédés et des compositions relatifs au VIH. Selon les procédés de l'invention, on peut cribler des analogues de nucléosides afin de déterminer leur capacité à être incorporés par la transcriptase inverse du virus d'immunodéficience humaine et provoquer un appariement incorrect entre bases. La mutation progressive du virus induite par de tels analogues de nucléosides permet de le rendre non viable.