硒吩-3-羧酸 | 35577-09-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硒吩
• 中文名称: 硒吩-3-羧酸
• 英文名称: selenophene-3-carboxylic acid
• 英文别名: 3-carboxy-selenophene；Selenophen-carbonsaeure-(3)；Selenophen-3-carbonsaeure；3-Carboxy-selenophen
• CAS: 35577-09-4
• 化学式: C₅H₄O₂Se
• 分子量: 175.046
• InChiKey: LPNFPTALNNSHRL-UHFFFAOYSA-N

物化性质

• 沸点：
  146-147 °C

计算性质

• 辛醇/水分配系数(LogP)：
  0.44
• 重原子数：
  8
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  硒吩-3-羧酸 在 ammonium hydroxide 、 氯化亚砜 、 乙醇 、 sodium ethanolate 、 四氯化锡 作用下， 反应 33.75h， 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：

  3-Cyanoselenophen 在 盐酸 作用下， 反应 1.0h， 以67%的产率得到硒吩-3-羧酸
  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

• Selenolopyrazole derivatives and use thereof as anticancer agents
  申请人：China Medical University

  公开号：US08053459B1

  公开（公告）日：2011-11-08

  The present invention synthesizes a series of selenolo[3,2-c]pyrazole and selenolo[2,3-c]pyrazole derivatives, and discovers their anticancer activity.

  本发明合成了一系列硒代[3,2-c]吡唑和硒代[2,3-c]吡唑衍生物，并发现它们的抗癌活性。
• Synthesis and in vitro anticancer activity of 6,7-methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-one analogs
  作者：Chien-Ting Chen、Mei-Hua Hsu、Yung-Yi Cheng、Chin-Yu Liu、Li-Chen Chou、Li-Jiau Huang、Tian-Shung Wu、Xiaoming Yang、Kuo-Hsiung Lee、Sheng-Chu Kuo

  DOI：10.1016/j.ejmech.2011.10.017

  日期：2011.12

  6,7-Methylenedioxy (or 5-hydroxy-6-methoxy)-2-(substituted selenophenyl)quinolin-4-ones and their isosteric compounds were synthesized and evaluated for anticancer activity. Structure activity relationships (SAR) of these compounds were established. Among all tested compounds, 6,7-methylenedioxy-2-(5-methylselenophen-2-yl)quinolin-4-one (4d) was found to be the most promising anticancer agent. In screening against NCI's 60 human tumor cell line panel, 4d exhibited highly selective and potent inhibitory activity against MDA-MB-435 melanoma. Furthermore, the results of COMPARE analysis suggested that 4d is an antimitotic agent with a different mechanism of action from the conventional antimitotic agents, such as colchicine, vinca alkaloids and paclitaxel. Therefore, 4d was identified as a new lead compound that merits further optimization. (C) 2011 Elsevier Masson SAS. All rights reserved.
• Selenosartans: Novel selenophene analogues of milfasartan and eprosartan
  作者：Rebecca L. Grange、James Ziogas、Andrea J. North、James A. Angus、Carl H. Schiesser

  DOI：10.1016/j.bmcl.2007.11.136

  日期：2008.2

  A series of selenophene analogues of the thiophene-containing anti hypertensives milfasartan and eprosartan were prepared and tested for AT(1) receptor antagonist properties. All four selenophene compounds proved to be potent AT(1) receptor antagonists, with pK(B) estimates indicating that these selenides are at least as effective as the thiophene parent compounds at blocking AT(1) receptor mediated responses. These results reveal that replacement of sulfur with selenium in thiophene-containing sartans does not interfere with sartan activity. (C) 2007 Elsevier Ltd. All rights reserved.
• Cathodic reduction of 3-substituted five-membered heteroaromatic acids
  作者：T. G. Konstantinova、V. P. Gul'tyai、V. P. Litvinov、A. Ya. Shteinshneider、E. D. Daeva、A. M. Moiseenkov

  DOI：10.1007/bf00953498

  日期：1983.4
• 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.

表征谱图