ethyl 2-β-D-ribofuranosylselenophene-3-carboxylate | 189145-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-β-D-ribofuranosylselenophene-3-carboxylate
• 英文别名: ethyl 2-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]selenophene-3-carboxylate
• CAS: 189145-43-5
• 化学式: C₁₂H₁₆O₆Se
• 分子量: 335.215
• InChiKey: YDGXYXJYZFJBSW-ZYUZMQFOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.93
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 2-β-D-ribofuranosylselenophene-3-carboxylate 在 ammonium hydroxide 作用下， 反应 8.0h， 以27.5%的产率得到2-β-D-ribofuranosylselenophene-3-carboxamide
  参考文献：
  名称：

  Synthesis, Structure, and Antiproliferative Activity of Selenophenfurin, an Inosine 5‘-Monophosphate Dehydrogenase Inhibitor Analogue of Selenazofurin

  摘要：

  The synthesis and biological activity of selenophenfurin (5-beta-D-ribofuranosylselenophene-3-carboxamide, 1), the selenophene analogue of selenazofurin, are described. Glycosylation of ethyl selenophene-3-carboxylate (6) under stannic chloride-catalyzed conditions gave 2- and 5-glycosylated regioisomers, as a mixture of alpha- and beta-anomers, and the beta-2,5-diglycosylated derivative. Deprotected ethyl 5-beta-D-ribofuranosylselenophene-3-carboxylate (12 beta) was converted into selenophenfurin by ammonolysis. The structure of 12 beta was determined by H-1- and C-13-NMR, crystallographic, and computational studies. Selenophenfurin proved to be antiproliferative against a number of leukemia, lymphoma, and solid tumor cell lines at concentrations similar to those of selenazofurin but was more potent than the thiophene and thiazole analogues thiophenfurin and tiazofurin. Incubation of K562 cells with selenophenfurin resulted in inhibition of IMP dehydrogenase (IMPDH) (76%) and an increase in IMP pools (14.5-fold) with a concurrent decrease in GTP levels (58%). The results obtained confirm the hypothesis that the presence of heteroatoms such as S or Se in the heterocycle in position 2 with respect to the glycosidic bond is essential for both cytotoxicity and IMP dehydrogenase inhibitory activity in this type of C-nucleosides.

  DOI：

  10.1021/jm960864o
• 作为产物：
  描述：

  四乙酰核糖 在 sodium ethanolate 、 四氯化锡 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 生成 ethyl 2-β-D-ribofuranosylselenophene-3-carboxylate
  参考文献：
  名称：

  Synthesis and Cytotoxic Activity of Selenophenfurin, a New Inhibitor of IMP Dehydrogenase

  摘要：

  The synthesis of 5-beta-D-ribofuranosylselenophene-3-carboxamide (selenophenfurin) is reported. Selenophenfurin was found active as cytotoxic agent and as inosine monophosphate dehydrogenase inhibitor.

  DOI：

  10.1080/07328319708006129

文献信息

• Synthesis, Structure, and Antiproliferative Activity of Selenophenfurin, an Inosine 5‘-Monophosphate Dehydrogenase Inhibitor Analogue of Selenazofurin
  作者：Palmarisa Franchetti、Loredana Cappellacci、Ghassan Abu Sheikha、Hiremagalur N. Jayaram、Vivek V. Gurudutt、Thaw Sint、Bryan P. Schneider、William D. Jones、Barry M. Goldstein、Graziella Perra、Antonella De Montis、Anna Giulia Loi、Paolo La Colla、Mario Grifantini

  DOI：10.1021/jm960864o

  日期：1997.5.1

  The synthesis and biological activity of selenophenfurin (5-beta-D-ribofuranosylselenophene-3-carboxamide, 1), the selenophene analogue of selenazofurin, are described. Glycosylation of ethyl selenophene-3-carboxylate (6) under stannic chloride-catalyzed conditions gave 2- and 5-glycosylated regioisomers, as a mixture of alpha- and beta-anomers, and the beta-2,5-diglycosylated derivative. Deprotected ethyl 5-beta-D-ribofuranosylselenophene-3-carboxylate (12 beta) was converted into selenophenfurin by ammonolysis. The structure of 12 beta was determined by H-1- and C-13-NMR, crystallographic, and computational studies. Selenophenfurin proved to be antiproliferative against a number of leukemia, lymphoma, and solid tumor cell lines at concentrations similar to those of selenazofurin but was more potent than the thiophene and thiazole analogues thiophenfurin and tiazofurin. Incubation of K562 cells with selenophenfurin resulted in inhibition of IMP dehydrogenase (IMPDH) (76%) and an increase in IMP pools (14.5-fold) with a concurrent decrease in GTP levels (58%). The results obtained confirm the hypothesis that the presence of heteroatoms such as S or Se in the heterocycle in position 2 with respect to the glycosidic bond is essential for both cytotoxicity and IMP dehydrogenase inhibitory activity in this type of C-nucleosides.
• Synthesis and Cytotoxic Activity of Selenophenfurin, a New Inhibitor of IMP Dehydrogenase
  作者：L. Cappellacci、P. Franchetti、G. Abu Sheikha、H. N. Jayaram、V. V. Gurudutt、T. Sint、B. P. Schneider、B. M. Goldstein、G. Perra、S. Poma、P. La Colla、M. Grifantini

  DOI：10.1080/07328319708006129

  日期：1997.7

  The synthesis of 5-beta-D-ribofuranosylselenophene-3-carboxamide (selenophenfurin) is reported. Selenophenfurin was found active as cytotoxic agent and as inosine monophosphate dehydrogenase inhibitor.