3'-amino-2',3'-dideoxy-5-dodecyloxymethyluridine | 1450644-52-6

• 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: 3'-amino-2',3'-dideoxy-5-dodecyloxymethyluridine
• 英文别名: 5-dodecyloxymethyl-3′-amino-2′,3′-dideoxyuridine；1-[(2R,4S,5S)-4-amino-5-(hydroxymethyl)tetrahydrofuran-2-yl]-5-(dodecoxymethyl)-4-hydroxy-pyrimidin-2-one；1-[(2R,4S,5S)-4-amino-5-(hydroxymethyl)oxolan-2-yl]-5-(dodecoxymethyl)pyrimidine-2,4-dione
• CAS: 1450644-52-6
• 化学式: C₂₂H₃₉N₃O₅
• 分子量: 425.569
• InChiKey: CSUCKKHSVQETJV-XUVXKRRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  30
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114
• 氢给体数：
  3
• 氢受体数：
  6

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	3'-azido-2',3'-dideoxy-5-dodecyloxymethyluridine	1450644-51-5	C22H37N5O5	451.566
  齐多夫定	3'-azido-2',3'-deoxythymidine	30516-87-1	C10H13N5O4	267.244
  ——	5'-O-acetyl-3'-azido-3'-deoxythymidine	66323-42-0	C12H15N5O5	309.282

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  ——	5-dodecyloxymethyl-3'-ethylamino-2',3'-dideoxyuridin	1450644-54-8	C24H43N3O5	453.623
  ——	5-dodecyloxymethyl-3'-diethylamino-2',3'-dideoxyuridine	1450644-53-7	C26H47N3O5	481.676

反应信息

• 作为反应物：
  描述：

  3'-amino-2',3'-dideoxy-5-dodecyloxymethyluridine 、 乙醛 以 乙醇 为溶剂， 反应 2.0h， 生成
  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
• 作为产物：
  描述：

  5'-O-acetyl-3'-azido-3'-deoxythymidine 在 DL-dithiothreitol 、 氨 、 水 、 溴 作用下， 以 1,4-二氧六环 、 乙醇 、 1,2-二氯乙烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.0h， 生成 3'-amino-2',3'-dideoxy-5-dodecyloxymethyluridine
  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

• 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.