ethyl selenophene-3-carboxylate | 67945-73-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硒吩
• 英文名称: ethyl selenophene-3-carboxylate
• CAS: 67945-73-7
• 化学式: C₇H₈O₂Se
• 分子量: 203.099
• InChiKey: ADCMRDUQQVUBIC-UHFFFAOYSA-N

物化性质

• 沸点：
  231.5±13.0 °C(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  10
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  ethyl selenophene-3-carboxylate 在 ammonium hydroxide 、 乙醇 、 sodium ethanolate 、 四氯化锡 作用下， 反应 28.0h， 生成 selenophenfurin
  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：

  硒吩-3-羧酸 在 氯化亚砜 作用下， 反应 5.75h， 生成 ethyl selenophene-3-carboxylate
  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

文献信息

• Multi‐Selenophene Incorporated Thiazole Imide‐Based n‐Type Polymers for High‐Performance Organic Thermoelectrics
  作者：Yongchun Li、Wenchang Wu、Yimei Wang、Enmin Huang、Sang Young Jeong、Han Young Woo、Xugang Guo、Kui Feng

  DOI：10.1002/anie.202316214

  日期：2024.1.15

  Developing polymers with high electrical conductivity (σ) after n‐doping is a great challenge for the advance of the field of organic thermoelectrics (OTEs). Herein, we report a series of thiazole imide‐based n‐type polymers by gradually increasing selenophene content in polymeric backbone. Thanks to the strong intramolecular noncovalent N⋅⋅⋅S interaction and enhanced intermolecular Se⋅⋅⋅Se interaction, with the increase of selenophene content, the polymers show gradually lowered LUMOs, more planar backbone, and improved film crystallinity versus the selenophene‐free analogue. Consequently, polymer PDTzSI−Se with the highest selenophene content achieves a champion σ of 164.0 S cm⁻¹ and a power factor of 49.0 μW m⁻¹ K⁻² in the series when applied in OTEs after n‐doping. The σ value is the highest one for n‐type donor‐acceptor OTE materials reported to date. Our work indicates that selenophene substitution is a powerful strategy for developing high‐performance n‐type OTE materials and selenophene incorporated thiazole imides offer an excellent platform in enabling n‐type polymers with high backbone coplanarity, deep‐lying LUMO and enhanced mobility/conductivity.

  摘要开发 n 掺杂后具有高导电率（σ）的聚合物是推动有机热电（OTE）领域发展的一大挑战。在此，我们报告了一系列基于噻唑亚胺的 n 型聚合物，其方法是逐渐增加聚合物骨架中的硒吩含量。因此，硒吩含量最高的聚合物 PDTzSI-Se 在 n 掺杂后应用于 OTE 时，其冠军 σ 为 164.0 S cm-1，功率因数为 49.0 μW m-1 K-2。该 σ 值是迄今为止报告的 n 型供体-受体 OTE 材料中最高的。我们的工作表明，硒吩取代是开发高性能 n 型 OTE 材料的有力策略，硒吩与噻唑亚胺的结合为实现具有高骨架共面性、深层 LUMO 和增强迁移率/电导率的 n 型聚合物提供了一个极好的平台。
• Selenium Substitution in Bithiophene Imide Polymer Semiconductors Enables High‐Performance <i>n</i> ‐Type Organic Thermoelectric
  作者：Jianfeng Li、Min Liu、Kun Yang、Yimei Wang、Junwei Wang、Zhicai Chen、Kui Feng、Dong Wang、Jianqi Zhang、Yongchun Li、Han Guo、Zhixiang Wei、Xugang Guo

  DOI：10.1002/adfm.202213911

  日期：——

  Designing n-type polymers with high electrical conductivity remains a major challenge for organic thermoelectrics (OTEs). Herein, by devising a novel selenophene-based electron-deficient building block, the pronounced advantages of selenium substitution in simultaneously enabling advanced n-type polymers is demonstrated with high mobility (≈2 orders of magnitude higher versus their sulfur-based analogues

  设计具有高导电性的n型聚合物仍然是有机热电材料 (OTE) 的主要挑战。在此，通过设计一种新型的基于硒吩的缺电子结构单元，硒取代在同时实现先进n型聚合物方面的显着优势被证明具有高迁移率（由于两者的原因，与其硫基类似物相比高约 2 个数量级）增强的链内和链间相互作用）和所得聚合物的n掺杂效率大大提高（通过大幅降低的 LUMO 水平和≈0.2 eV 裕度实现）。通过侧链优化和供体工程，硒取代聚合物 f-BSeI2TEG-FT 实现了 103.5 S cm -1的最高电导率和 70.1 µW m -1  K -2的功率因数，这是文献中报道的n型聚合物的最高值之​​一，f-BSeI2TEG-FT 的电导率增加 40%，大大优于硫基模拟聚合物。这些结果表明，硒替代是提高n型性能的一种非常有效的策略，并为开发高性能n型 OTE 材料提供了重要的结构-性能相关性。
• DECROIX B.; DUBUS P.; MOREL J.; PASTOUR P., BULL. SOC. CHIM. FRANCE <BSCF-AS>, 1976, NO 3-4, PART. 2, 621-627
  作者：DECROIX B.、 DUBUS P.、 MOREL J.、 PASTOUR P.

  DOI：——

  日期：——
• 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.