| 917377-37-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• CAS: 917377-37-8
• 化学式: C₁₁H₁₃FN₂O₄S
• 分子量: 288.3
• InChiKey: XOWLOJQDZMCERS-MRTMQBJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.09
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  81.16
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 1H-1,2,4-三唑 、 三氯氧磷 、 ammonium hydroxide 作用下， 以 1,4-二氧六环 为溶剂， 以9 mg的产率得到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-butyl(diphenyl)silyl]oxymethyl]-4-phenylmethoxythiolan-3-ol 在 吡啶 、 4-二甲氨基吡啶 、 二乙胺基三氟化硫 、 四丁基氟化铵 、 sodium methylate 、 三氯化硼 、 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 21.17h， 生成
  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.