selenophenfurin | 189145-39-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: selenophenfurin
• 英文别名: 5-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]selenophene-3-carboxamide
• CAS: 189145-39-9
• 化学式: C₁₀H₁₃NO₅Se
• 分子量: 306.177
• InChiKey: WWPFTXUYJRVAIJ-YYNOVJQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.0
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  113
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  selenophenfurin 在 盐酸 、 磷酸三乙酯 、 碳酸 、 水 、 三乙胺 、 原甲酸三乙酯 、 三氯氧磷 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 54.0h， 生成
  参考文献：
  名称：

  呋喃呋喃，噻吩呋喃和硒代苯呋喃衍生的烟酰胺腺嘌呤二核苷酸的等规类似物，是哺乳动物肌苷单磷酸脱氢酶（I和II型）的抑制剂。

  摘要：

  二核苷酸TFAD（6），FFAD（7）和SFAD（8），分别来自C-核苷5-β-d-核呋喃糖基噻吩-3-甲酰胺（thiophenfurin，1），5-beta-d的等排NAD类似物作为人肌苷单磷酸脱氢酶（IMPDH）的I型和II型抑制剂，合成了-呋喃呋喃糖基呋喃-3-羧酰胺（呋喃呋喃2）和5-β-d-呋喃核糖基硒吩3-羧酰胺（硒苯吩呋喃5）。合成是通过咪唑催化的1、2和5的5'-单磷酸酯与AMP偶联而进行的。这些二核苷酸也是噻唑-4-羧酰胺腺嘌呤二核苷酸（TAD）和硒唑-4-羧酰胺腺嘌呤二核苷酸（SAD）的类似物，它们是溶瘤性C-核苷2-β-D-核呋喃呋喃糖基噻唑-4-羧酰胺的活性代谢产物。 （tiazofurin）和2-beta-D-rifurfuranosylselenazole-4-carboxamide（selenazofurin），评估了它们对重组人IMPDH和I型II的抑制能力

  DOI：

  10.1021/jm970772e
• 作为产物：
  描述：

  ethyl 5-β-D-ribofuranosylselenophene-3-carboxylate 在 ammonium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 生成 selenophenfurin
  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 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.
• 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.
• Isosteric Analogues of Nicotinamide Adenine Dinucleotide Derived from Furanfurin, Thiophenfurin, and Selenophenfurin as Mammalian Inosine Monophosphate Dehydrogenase (Type I and II) Inhibitors
  作者：Palmarisa Franchetti、Loredana Cappellacci、Paolo Perlini、Hiremagalur N. Jayaram、Adrian Butler、Bryan P. Schneider、Frank R. Collart、Eliezer Huberman、Mario Grifantini

  DOI：10.1021/jm970772e

  日期：1998.5.1

  respectively, from C-nucleosides 5-beta-d-ribofuranosylthiophene-3-carboxamide (thiophenfurin, 1), 5-beta-d-ribofuranosylfuran-3-carboxamide (furanfurin, 2), and 5-beta-d-ribofuranosylselenophene-3-carboxamide (selenophenfurin, 5), were synthesized as human inosine monophosphate dehydrogenase (IMPDH) type I and II inhibitors. The synthesis was carried out by imidazole-catalyzed coupling of the 5'-monophosphate

  二核苷酸TFAD（6），FFAD（7）和SFAD（8），分别来自C-核苷5-β-d-核呋喃糖基噻吩-3-甲酰胺（thiophenfurin，1），5-beta-d的等排NAD类似物作为人肌苷单磷酸脱氢酶（IMPDH）的I型和II型抑制剂，合成了-呋喃呋喃糖基呋喃-3-羧酰胺（呋喃呋喃2）和5-β-d-呋喃核糖基硒吩3-羧酰胺（硒苯吩呋喃5）。合成是通过咪唑催化的1、2和5的5'-单磷酸酯与AMP偶联而进行的。这些二核苷酸也是噻唑-4-羧酰胺腺嘌呤二核苷酸（TAD）和硒唑-4-羧酰胺腺嘌呤二核苷酸（SAD）的类似物，它们是溶瘤性C-核苷2-β-D-核呋喃呋喃糖基噻唑-4-羧酰胺的活性代谢产物。 （tiazofurin）和2-beta-D-rifurfuranosylselenazole-4-carboxamide（selenazofurin），评估了它们对重组人IMPDH和I型II的抑制能力