3'-O-(tert-butyldimethylsilyl)-2'-deoxy-N-(2,2-dimethyl-1-oxopropyl)adenosine | 958649-36-0

• 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: 3'-O-(tert-butyldimethylsilyl)-2'-deoxy-N-(2,2-dimethyl-1-oxopropyl)adenosine
• CAS: 958649-36-0
• 化学式: C₂₁H₃₅N₅O₄Si
• 分子量: 449.625
• InChiKey: NBKMTNIOLCTECP-RRFJBIMHSA-N

反应信息

• 作为反应物：
  描述：

  3'-O-(tert-butyldimethylsilyl)-2'-deoxy-N-(2,2-dimethyl-1-oxopropyl)adenosine 、 溴甲苯 在 potassium tert-butylate 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 以97%的产率得到5'-O-benzyl-3'-O-(tert-butyldimethylsilyl)-2'-deoxy-N-(2,2-dimethyl-1-oxopropyl)adenosine
  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：

  在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 1.5h， 以324 mg的产率得到3'-O-(tert-butyldimethylsilyl)-2'-deoxy-N-(2,2-dimethyl-1-oxopropyl)adenosine
  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