2-[(2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy]ethyl 4-oxo-4-{[3-((3S)-3,7,10-trimethyl-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecan-1-yl)propyl]amino}butanoate

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-[(2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy]ethyl 4-oxo-4-{[3-((3S)-3,7,10-trimethyl-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecan-1-yl)propyl]amino}butanoate
• 英文别名: 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl 4-oxo-4-[3-[(3S)-3,7,10-trimethyl-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecan-1-yl]propylamino]butanoate
• 化学式: C₂₄H₃₉N₇O₈Si
• 分子量: 581.701
• InChiKey: CZLNWDNXDLOKGO-AKABYQOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.01
• 重原子数：
  40
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  181
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  阿昔洛韦 在 吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 2-[(2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy]ethyl 4-oxo-4-{[3-((3S)-3,7,10-trimethyl-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecan-1-yl)propyl]amino}butanoate
  参考文献：
  名称：

  Synthesis and biological evaluation of nucleoside analogues than contain silatrane on the basis of the structure of acyclovir (ACV) as novel inhibitors of hepatitis B virus (HBV)

  摘要：

  Hepatitis B virus (HBV) infection causes major public health problems worldwide. Acyclovir (ACV) is mainly used to inhibit herpes simplex virus (HSV) rather than HBV. In this study, we used the combination principle to design and synthesize nucleoside analogues that contain silatrane on the basis of the structure of ACV. We found that the compounds were effective inhibitors of HBV, both in vitro and in vivo. All of the compounds showed suppressive activity on the expression of HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) in the HepG2.2.15 cell line with low cytotoxicity. One of compounds was studied in HBV transgenic mice model, and the test results showed its ability to reduce the levels of HBsAg, HBeAg and HBV DNA by ELASE and qPCR. Furthermore, significant improvement of T lymphocyte was observed after treatment, as evaluated by flow cytometry (FCM). (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.097

文献信息

• Synthesis and biological evaluation of nucleoside analogues than contain silatrane on the basis of the structure of acyclovir (ACV) as novel inhibitors of hepatitis B virus (HBV)
  作者：Anyue Han、Lingna Li、Kuiyou Qing、Xiaolu Qi、Leping Hou、Xintong Luo、Shaohua Shi、Faqing Ye

  DOI：10.1016/j.bmcl.2012.12.097

  日期：2013.3

  Hepatitis B virus (HBV) infection causes major public health problems worldwide. Acyclovir (ACV) is mainly used to inhibit herpes simplex virus (HSV) rather than HBV. In this study, we used the combination principle to design and synthesize nucleoside analogues that contain silatrane on the basis of the structure of ACV. We found that the compounds were effective inhibitors of HBV, both in vitro and in vivo. All of the compounds showed suppressive activity on the expression of HBV surface antigen (HBsAg) and HBV e antigen (HBeAg) in the HepG2.2.15 cell line with low cytotoxicity. One of compounds was studied in HBV transgenic mice model, and the test results showed its ability to reduce the levels of HBsAg, HBeAg and HBV DNA by ELASE and qPCR. Furthermore, significant improvement of T lymphocyte was observed after treatment, as evaluated by flow cytometry (FCM). (C) 2013 Elsevier Ltd. All rights reserved.