9-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-β-D-2-deoxyribofuranosyl]-6-chloropurine | 958649-32-6

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 9-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-β-D-2-deoxyribofuranosyl]-6-chloropurine
• CAS: 958649-32-6
• 化学式: C₂₃H₂₉ClN₄O₄Si
• 分子量: 489.046
• InChiKey: XFOCKKUVYRQLOA-RCCFBDPRSA-N

反应信息

• 作为反应物：
  描述：

  9-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-β-D-2-deoxyribofuranosyl]-6-chloropurine 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 6.0h， 以72%的产率得到9-(5-O-benzoyl-β-D-2-deoxyribofuranosyl)-6-chloropurine
  参考文献：
  名称：

  5′-O-Masked 2′-deoxyadenosine analogues as lead compounds for hepatitis C virus (HCV) therapeutic agents

  摘要：

  On the basis of our previous Study on antiviral agents against the severe acute respiratory syndrome (SARS) coronavirus, a series of nucleoside analogues whose 5'-hydroxyl groups are masked by various protective groups such as carboxylate, sulfortate, and ether were synthesized and evaluated to develop novel anti-hepatitis C virus (HCV) agents. Among these, several 5'-O-masked analogues of 6-chloropurine-2'-deoxyiriboside (e.g., 5'-O-benzoyl, 5'-O-p-methoxybenzoyl and 5'-O-benzyl analogues) were found to exhibit effective anti-HCV activity. In particular, the 5'-O-benzoyl analogue exhibited the highest potency with an EC50 of 6.1 JAM in a cell-based HCV replicon assay. Since the 5'-O-unmasked analogue (i.e., 6-chloropurine-2'-deoxyriboside) was not sufficiently potent (EC50 = 47.2 mu M), masking of the 5'-hydroxyl group seems to be an effective method for the development of anti-HCV agents. Presently, we hypothesize two roles for the 5'-O-masked analogues: One is the role as an anti-HCV agent by itself, and the other is as a prodrug of its 5'-0-demasked (deprotected) derivative. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.025
• 作为产物：
  描述：

  5'-O-benzoyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxyadenosine 在 亚硝酸特丁酯 、 四乙基氯化铵 作用下， 以 四氯化碳 、 二氯甲烷 为溶剂， 反应 3.5h， 以58%的产率得到9-[5-O-benzoyl-3-O-(tert-butyldimethylsilyl)-β-D-2-deoxyribofuranosyl]-6-chloropurine
  参考文献：
  名称：

  5′-O-Masked 2′-deoxyadenosine analogues as lead compounds for hepatitis C virus (HCV) therapeutic agents

  摘要：

  On the basis of our previous Study on antiviral agents against the severe acute respiratory syndrome (SARS) coronavirus, a series of nucleoside analogues whose 5'-hydroxyl groups are masked by various protective groups such as carboxylate, sulfortate, and ether were synthesized and evaluated to develop novel anti-hepatitis C virus (HCV) agents. Among these, several 5'-O-masked analogues of 6-chloropurine-2'-deoxyiriboside (e.g., 5'-O-benzoyl, 5'-O-p-methoxybenzoyl and 5'-O-benzyl analogues) were found to exhibit effective anti-HCV activity. In particular, the 5'-O-benzoyl analogue exhibited the highest potency with an EC50 of 6.1 JAM in a cell-based HCV replicon assay. Since the 5'-O-unmasked analogue (i.e., 6-chloropurine-2'-deoxyriboside) was not sufficiently potent (EC50 = 47.2 mu M), masking of the 5'-hydroxyl group seems to be an effective method for the development of anti-HCV agents. Presently, we hypothesize two roles for the 5'-O-masked analogues: One is the role as an anti-HCV agent by itself, and the other is as a prodrug of its 5'-0-demasked (deprotected) derivative. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.08.025