1-[(3S,4S,5R)-4-fluoro-5-(hydroxymethyl)thiolan-3-yl]pyrimidine-2,4-dione | 917377-23-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-[(3S,4S,5R)-4-fluoro-5-(hydroxymethyl)thiolan-3-yl]pyrimidine-2,4-dione
• CAS: 917377-23-2
• 化学式: C₉H₁₁FN₂O₃S
• 分子量: 246.262
• InChiKey: DYSOEHXNULVIHQ-JKMUOGBPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  94.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-[(3S,4S,5R)-4-fluoro-5-(hydroxymethyl)thiolan-3-yl]pyrimidine-2,4-dione 在 吡啶 、 1H-1,2,4-三唑 、 三氯氧磷 作用下， 生成 4-amino-1-[(3S,4S,5R)-4-fluoro-5-(hydroxymethyl)thiolan-3-yl]pyrimidin-2-one
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives

  摘要：

  Novel iso-D-2',3'-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIR Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.066
• 作为产物：
  描述：

  (+)-(3S,4S,5R)-5-(tert-butyldiphenylsilanyloxymethyl)-4-fluorotetrahydrothien-3-ol 在 四丁基氟化铵 、 sodium methylate 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 1-[(3S,4S,5R)-4-fluoro-5-(hydroxymethyl)thiolan-3-yl]pyrimidine-2,4-dione
  参考文献：
  名称：

  Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives

  摘要：

  Novel iso-D-2',3'-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIR Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2006.09.066

文献信息

• Design, Enantiopure Synthesis, and Biological Evaluation of Novel ISO-D-2′,3′-Dideoxy-3′-Fluorothianucleoside Derivatives as a bioisostere of Lamivudine
  作者：Kyung Ran Kim、Ah-Young Park、Hyung Ryong Moon、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1080/15257770701506426

  日期：2007.11.26

  Novel isoD-2',3'-dideoxythianucleoside derivatives 1-3 were designed and asymmetrically synthesized to search for new anti-HIV agents. Final compounds 1-3 were evaluated against a variety of viruses including HIV-1 and 2. Only cytosine analog 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso 2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent.
• Design, synthesis, and biological evaluation of novel iso-d-2′,3′-dideoxy-3′-fluorothianucleoside derivatives
  作者：Kyung Ran Kim、Hyung Ryong Moon、Ah-Young Park、Moon Woo Chun、Lak Shin Jeong

  DOI：10.1016/j.bmc.2006.09.066

  日期：2007.1.1

  Novel iso-D-2',3'-dideoxythianucleoside derivatives 1-4 were designed and asymmetrically synthesized as a bioisostere of lamivudine to search for new anti-HIV agents. The information about using sulfur participation occurred on DAST fluorination and Mitsunobu reaction will be of great help in synthesizing sulfur-containing compounds. Final compounds 1-4 were evaluated against HIV-1 and 2, HSV-1 and 2, EMCV, Cox. B3, VSV, FluA (Taiwan), FluA (Johan.), FCV, and FIR Only cytosine analogue 3 showed a potent anti-VSV activity (EC50 = 9.43 mu g/mL). This result implies that iso-2',3'-dideoxy sugar templates might play a role of a sugar surrogate of nucleosides for the development of anti-RNA virus agent. (c) 2006 Elsevier Ltd. All rights reserved.