3-benzoyl-1-[3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydro-selenophen-2-yl]-1H-pyrimidine-2,4-dione | 1187425-06-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 3-benzoyl-1-[3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydro-selenophen-2-yl]-1H-pyrimidine-2,4-dione
• 英文别名: 3-benzoyl-1-[(2R,3S,4S,5R)-3-hydroxy-4-(oxan-2-yloxy)-5-(trityloxymethyl)selenolan-2-yl]pyrimidine-2,4-dione
• CAS: 1187425-06-4
• 化学式: C₄₀H₃₈N₂O₇Se
• 分子量: 737.711
• InChiKey: WAMDJCINIVHMFY-QXGVGYHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.98
• 重原子数：
  50
• 可旋转键数：
  10
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  106
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3-benzoyl-1-[3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydro-selenophen-2-yl]-1H-pyrimidine-2,4-dione 在 二乙胺基三氟化硫 作用下， 以 二氯甲烷 为溶剂， 以45%的产率得到3-benzoyl-1-[3-fluoro-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydro-selenophen-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Discovery of a New Template for Anticancer Agents: 2′-deoxy-2′-fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-Seleno-ara-C)

  摘要：

  The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent anticancer activity in all cancer cell lines tested and was more potent than ara-C (1).

  DOI：

  10.1021/jm900852b
• 作为产物：
  描述：

  3-benzoyl-1-((2R,3S,4S,5R)-4-((tetrahydro-2H-pyran-2-yl)oxy)-3-((triethylsilyl)oxy)-5-((trityloxy)methyl)tetrahydroselenophen-2-yl)pyrimidine-2,4(1H,3H)-dione 在 四丁基氟化铵 、 溶剂黄146 作用下， 以 四氢呋喃 为溶剂， 反应 0.25h， 以99%的产率得到3-benzoyl-1-[3-hydroxy-4-(tetrahydro-pyran-2-yloxy)-5-trityloxymethyl-tetrahydro-selenophen-2-yl]-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Discovery of a New Template for Anticancer Agents: 2′-deoxy-2′-fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-Seleno-ara-C)

  摘要：

  The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent anticancer activity in all cancer cell lines tested and was more potent than ara-C (1).

  DOI：

  10.1021/jm900852b

文献信息

• Discovery of a New Template for Anticancer Agents: 2′-deoxy-2′-fluoro-4′-selenoarabinofuranosyl-cytosine (2′-F-4′-Seleno-ara-C)
  作者：Lak Shin Jeong、Dilip K. Tosh、Won Jun Choi、Sang Kook Lee、You-Jin Kang、Sun Choi、Jin Hee Lee、Hankil Lee、Hyuk Woo Lee、Hea Ok Kim

  DOI：10.1021/jm900852b

  日期：2009.9.10

  The first synthesis of 2'-deoxy-2'-fluoro-4'-selenoarabinofuranosyl pyrimidines as potent anticancer agents was accomplished using the DAST fluorination as a key step. It was first revealed that selenium atom participated in the DAST fluorination of 4'-selenonucleosides and that conformational bias induced by bulky selenium acted as a decisive factor in the DAST fluorination. Among compounds tested, 2'-F-4'-seleno-ara-C (4a) exhibited highly potent anticancer activity in all cancer cell lines tested and was more potent than ara-C (1).