3-硒吩羰基氯化物 | 75529-68-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 硒吩
• 中文名称: 3-硒吩羰基氯化物
• 中文别名: 2-环丁烯-1-酮,3-甲氧基-(9CI)
• 英文名称: Selenophen-3-carbonsaeurechlorid
• 英文别名: selenophene-3-carbonyl chloride；Selenophen-carbonsaeure-(3)-chlorid
• CAS: 75529-68-9
• 化学式: C₅H₃ClOSe
• 分子量: 193.491
• InChiKey: SPDHFEGMNPCZOA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.12
• 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：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-硒吩羰基氯化物 在 ammonium hydroxide 、 乙醇 、 sodium ethanolate 、 四氯化锡 作用下， 反应 33.0h， 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， 以 二氯甲烷 为溶剂， 反应 20.0h， 生成 3-硒吩羰基氯化物
  参考文献：
  名称：

  Selenolopyrazole derivatives and use thereof as anticancer agents

  摘要：

  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。

  公开号：

  US08053459B1

文献信息

• Organische photochemie
  作者：Klaus Beelitz、Klaus Praefcke、Salo Gronowitz

  DOI：10.1016/s0022-328x(00)86665-6

  日期：1980.7

  The two new ring systems 9H-selenolo[3,2-b][1]benzoselenine and 4H-selenolo [2,3-b][1]benzoselenine are described; these compounds are synthesized by photoinduced selenol esterseleninone transformations of Se-p-tolylselenophenselenocarboxylates

  描述了两个新的环系统9 H-硒代[3,2- b ] [1]苯并硒氨酸和4 H-硒代[2,3- b ] [1]苯并硒氨酸；这些化合物由光诱导的硒醇esterseleninone变换合成硒- p -tolylselenophenselenocarboxylates
• Beelitz, Klaus; Praefcke, Klaus; Gronowitz, Salo, Liebigs Annalen der Chemie, 1980, # 10, p. 1597 - 1603
  作者：Beelitz, Klaus、Praefcke, Klaus、Gronowitz, Salo

  DOI：——

  日期：——
• 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.
• BEELITZ K.; PRAEFCKE K.; GRONOWITZ S., J. ORGANOMETAL. CHEM., 1980, 194, NO 2, 167-171
  作者：BEELITZ K.、 PRAEFCKE K.、 GRONOWITZ S.

  DOI：——

  日期：——
• BEELITZ K.; PRAEFCKE K., LIEBIGS ANN. CHEM. 1980, NO 10, 1597-1603,
  作者：BEELITZ K.、 PRAEFCKE K.

  DOI：——

  日期：——