5-[(4-octyl)-1,2,3-triazol-1-yl]methyl-2′-deoxyuridine | 1450644-59-3

• 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: 5-[(4-octyl)-1,2,3-triazol-1-yl]methyl-2′-deoxyuridine
• 英文别名: 5-(4-octyl-1,2,3-triazol-1-yl)methyl-2'-deoxyuridine；4-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-[(4-octyltriazol-1-yl)methyl]pyrimidin-2-one；1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-[(4-octyltriazol-1-yl)methyl]pyrimidine-2,4-dione
• CAS: 1450644-59-3
• 化学式: C₂₀H₃₁N₅O₅
• 分子量: 421.497
• InChiKey: NFGISSQTRAYCOD-RCCFBDPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  130
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3',5'-di-O-acetyl-5-bromomethyl-2'-deoxyuridine 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 氨 、 水 、 sodium ascorbate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 38.0h， 生成 5-[(4-octyl)-1,2,3-triazol-1-yl]methyl-2′-deoxyuridine
  参考文献：
  名称：

  Inhibition of Mycobacterium tuberculosis strains H37Rv and MDR MS-115 by a new set of C5 modified pyrimidine nucleosides

  摘要：

  Two sets of pyrimidine nucleoside derivatives bearing extended alkyloxymethyl or alkyltriazolidomethyl substituents at position 5 of the nucleobase were synthesized and evaluated as potential antituberculosis agents. The impact of modifications at 3'- and 5'-positions of the carbohydrate moiety on the antimycobacterial activity and cytotoxicity was studied. The highest effect was shown for 5-dodecyloxymethyl-2'-deoxyuridine, 5-decyltriazolidomethyl-2'-deoxyuridine, and 5-dodecyltriazolidomethyl-2'-deoxycytidine. They effectively inhibited the growth of two Mycobacterium tuberculosis strains in vitro, laboratory H37Rv (MIC99 = 20, 10, and 20 mu g/mL, respectively) and clinical MDR MS-115 resistant to five top antituberculosis drugs (MIC99 = 50, 10, and 10 mu g/mL, respectively). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.07.003

文献信息

• 5-(4-alkyl-1,2,3-triazol-1-yl)methyl derivatives of 2′-deoxyuridine as inhibitors of viral and bacterial growth
  作者：L. A. Alexandrova、O. V. Efremenkova、V. L. Andronova、G. A. Galegov、P. N. Solyev、I. L. Karpenko、S. N. Kochetkov

  DOI：10.1134/s1068162016050022

  日期：2016.11

  A series of 5-(4-alkyl-1,2,3-triazol-1-yl)methyl derivatives of 2′-deoxyuridine have been synthesized by the interaction of 3′,5′-diacetyl-5-azidomethyl-2′-deoxyuridine with the corresponding 1-alkynes in a biphasic methylene chloride—water system catalyzed by Cu(I) followed by the deblocking with a water-alcohol ammonia solution. A low cytotoxicity of the compounds in Vero, Jurkat, and A549 cell cultures

  通过3',5'-二乙酰-5-叠氮甲基-2'的相互作用合成了一系列2'-脱氧尿苷的5-(4-烷基-1,2,3-三唑-1-基)甲基衍生物-脱氧尿苷与相应的 1-炔烃在双相二氯甲烷 - 水系统中由 Cu(I) 催化，然后用水 - 醇氨溶液解封。已显示这些化合物在 Vero、Jurkat 和 A549 细胞培养物中的低细胞毒性。2'-脱氧尿苷衍生物在体外对人类单纯疱疹病毒 1 型 (HSV-1) 的两种实验室毒株表现出抗疱疹活性：阿昔洛韦敏感 (HSV-1/L2) 和阿昔洛韦耐药 (HSV-1/L2RACV) . 它们还在体外抑制了一些细菌（耻垢分枝杆菌、金黄色葡萄球菌、藤黄微球菌和肠系膜明串珠菌）和酵母酿酒酵母的生长。
• Inhibition of Mycobacterium tuberculosis strains H37Rv and MDR MS-115 by a new set of C5 modified pyrimidine nucleosides
  作者：Eduard R. Shmalenyuk、Larisa N. Chernousova、Inna L. Karpenko、Sergey N. Kochetkov、Tatiana G. Smirnova、Sofia N. Andreevskaya、Alexander O. Chizhov、Olga V. Efremenkova、Ludmila A. Alexandrova

  DOI：10.1016/j.bmc.2013.07.003

  日期：2013.9

  Two sets of pyrimidine nucleoside derivatives bearing extended alkyloxymethyl or alkyltriazolidomethyl substituents at position 5 of the nucleobase were synthesized and evaluated as potential antituberculosis agents. The impact of modifications at 3'- and 5'-positions of the carbohydrate moiety on the antimycobacterial activity and cytotoxicity was studied. The highest effect was shown for 5-dodecyloxymethyl-2'-deoxyuridine, 5-decyltriazolidomethyl-2'-deoxyuridine, and 5-dodecyltriazolidomethyl-2'-deoxycytidine. They effectively inhibited the growth of two Mycobacterium tuberculosis strains in vitro, laboratory H37Rv (MIC99 = 20, 10, and 20 mu g/mL, respectively) and clinical MDR MS-115 resistant to five top antituberculosis drugs (MIC99 = 50, 10, and 10 mu g/mL, respectively). (C) 2013 Elsevier Ltd. All rights reserved.