6-[(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-[1,3]oxathiolan-5-yl]-5-oxo-5,6-dihydro-imidazo[1,2-c]pyrimidine-2-carboxylic acid ethyl ester | 188251-87-8

• 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: 6-[(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-[1,3]oxathiolan-5-yl]-5-oxo-5,6-dihydro-imidazo[1,2-c]pyrimidine-2-carboxylic acid ethyl ester
• 英文别名: ethyl 6-[(2S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-1,3-oxathiolan-5-yl]-5-oxoimidazo[1,2-c]pyrimidine-2-carboxylate
• CAS: 188251-87-8
• 化学式: C₁₉H₂₉N₃O₅SSi
• 分子量: 439.608
• InChiKey: IFPJXJIAYWEOME-CVEARBPZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.28
• 重原子数：
  29
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  108
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  6-[(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-[1,3]oxathiolan-5-yl]-5-oxo-5,6-dihydro-imidazo[1,2-c]pyrimidine-2-carboxylic acid ethyl ester 在 lithium aluminium tetrahydride 、 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 2-Hydroxymethyl-6-((2S,5R)-2-hydroxymethyl-[1,3]oxathiolan-5-yl)-6H-imidazo[1,2-c]pyrimidin-5-one
  参考文献：
  名称：

  Discovery of imidazo[1,2-c]pyrimidin-5(6H)-one heterosubstituted nucleoside analogues with potent activity against human hepatitis B virus in vitro

  摘要：

  The in vitro antihepatitis B virus (HBV) activities of eleven novel imidazo[1,2-c]pyrimidin-5(6H)-one dideoxynucleoside analogues in which the sugar ring is 1,3-dioxolane or 1,3-oxathiolane were compared in the chronically HBV-producing human cell line 2.2.15. Seven nucleoside analogues 4, 9, 10, 15, 16, Is, and 24, of which 16 possesses the tra,ls relative stereochemistry, displayed good potency and selectivity towards HBV. The order of decreasing potency at the 90% extracellular DNA inhibition level was 15>16>24 approximate to 9>10>18. None of the tested imidazo[1,2-c]pyrimidines inhibited the replication of HIV-1 in MT-4 cells. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00001-2
• 作为产物：
  描述：

  ent-拉米夫定 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 6-[(2S,5R)-2-(tert-Butyl-dimethyl-silanyloxymethyl)-[1,3]oxathiolan-5-yl]-5-oxo-5,6-dihydro-imidazo[1,2-c]pyrimidine-2-carboxylic acid ethyl ester
  参考文献：
  名称：

  Discovery of imidazo[1,2-c]pyrimidin-5(6H)-one heterosubstituted nucleoside analogues with potent activity against human hepatitis B virus in vitro

  摘要：

  The in vitro antihepatitis B virus (HBV) activities of eleven novel imidazo[1,2-c]pyrimidin-5(6H)-one dideoxynucleoside analogues in which the sugar ring is 1,3-dioxolane or 1,3-oxathiolane were compared in the chronically HBV-producing human cell line 2.2.15. Seven nucleoside analogues 4, 9, 10, 15, 16, Is, and 24, of which 16 possesses the tra,ls relative stereochemistry, displayed good potency and selectivity towards HBV. The order of decreasing potency at the 90% extracellular DNA inhibition level was 15>16>24 approximate to 9>10>18. None of the tested imidazo[1,2-c]pyrimidines inhibited the replication of HIV-1 in MT-4 cells. (C) 1997, Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00001-2

文献信息

• Discovery of imidazo[1,2-c]pyrimidin-5(6H)-one heterosubstituted nucleoside analogues with potent activity against human hepatitis B virus in vitro
  作者：Tarek S. Mansour、Colleen A. Evans、Marie Charron、Brent E. Korba

  DOI：10.1016/s0960-894x(97)00001-2

  日期：1997.2

  The in vitro antihepatitis B virus (HBV) activities of eleven novel imidazo[1,2-c]pyrimidin-5(6H)-one dideoxynucleoside analogues in which the sugar ring is 1,3-dioxolane or 1,3-oxathiolane were compared in the chronically HBV-producing human cell line 2.2.15. Seven nucleoside analogues 4, 9, 10, 15, 16, Is, and 24, of which 16 possesses the tra,ls relative stereochemistry, displayed good potency and selectivity towards HBV. The order of decreasing potency at the 90% extracellular DNA inhibition level was 15>16>24 approximate to 9>10>18. None of the tested imidazo[1,2-c]pyrimidines inhibited the replication of HIV-1 in MT-4 cells. (C) 1997, Elsevier Science Ltd.