• 文献检索
  • 文档翻译
  • 深度研究
  • 学术资讯
  • Suppr Zotero 插件Zotero 插件
  • 邀请有礼
  • 套餐&价格
  • 历史记录
应用&插件
Suppr Zotero 插件Zotero 插件浏览器插件Mac 客户端Windows 客户端微信小程序
定价
高级版会员购买积分包购买API积分包
服务
文献检索文档翻译深度研究API 文档MCP 服务
关于我们
关于 Suppr公司介绍联系我们用户协议隐私条款
关注我们

Suppr 超能文献

核心技术专利：CN118964589B侵权必究
粤ICP备2023148730 号-1Suppr @ 2026

文献检索

告别复杂PubMed语法，用中文像聊天一样搜索，搜遍4000万医学文献。AI智能推荐，让科研检索更轻松。

立即免费搜索

文件翻译

保留排版，准确专业，支持PDF/Word/PPT等文件格式，支持 12+语言互译。

免费翻译文档

深度研究

AI帮你快速写综述，25分钟生成高质量综述，智能提取关键信息，辅助科研写作。

立即免费体验

通过1,3-偶极环加成反应区域选择性合成5-取代的3-(β-D-吡喃葡萄糖基)异恶唑和异恶唑啉作为潜在抗癌剂和糖原磷酸化酶抑制剂。

Regioselective Synthesis of 5-Substituted 3-(β-d-Glycopyranosyl)isoxazoles and -isoxazolines by 1,3-Dipolar Cycloaddition as Potential Anticancer Agents and Glycogen Phosphorylase Inhibitors.

作者信息

Kaszás Tímea, Szakács Bence, Bertalan Márta, Blága Tekla, Hameed Faria, Lengyel Ákos, Saifi Samreen, Juhász-Tóth Éva, Varga Luca A, Docsa Tibor, Sipos Adrienn, Bai Péter, Ábrahám Anita, Kiss-Szikszai Attila, Kun Sándor, Kiss György Attila, József János, Juhász László, Tóth Marietta

机构信息

Department of Organic Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary.

Doctoral School of Chemistry, University of Debrecen, P.O. Box 400, H-4002 Debrecen, Hungary.

出版信息

Int J Mol Sci. 2025 Aug 22;26(17):8167. doi: 10.3390/ijms26178167.

DOI:10.3390/ijms26178167
PMID:40943091
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12427784/
Abstract

Anhydro-aldose oximes were employed to generate in situ nitrile oxides via a halogenation/base-induced elimination sequence in the presence of NCS and EtN, which were then used in 1,3-dipolar cycloadditions with alkenes and alkynes to afford 5-substituted 3-(β-d-glycopyranosyl)isoxazole and -isoxazoline derivatives exclusively. These newly synthesized glycomimetics were evaluated for their potential to act as antagonists of A2780 ovarian cancer cells and as inhibitors of glycogen phosphorylase; however, they exhibited no significant activity.

摘要

脱水醛糖肟在NCS和EtN存在下，通过卤化/碱诱导消除序列原位生成腈氧化物，然后将其用于与烯烃和炔烃的1,3-偶极环加成反应，专门得到5-取代的3-(β-D-吡喃葡萄糖基)异恶唑和异恶唑啉衍生物。对这些新合成的糖模拟物作为A2780卵巢癌细胞拮抗剂和糖原磷酸化酶抑制剂的潜力进行了评估；然而，它们没有表现出显著活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/84ebcbc1ff04/ijms-26-08167-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/ccdb53a31922/ijms-26-08167-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/f21280b38aa9/ijms-26-08167-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/11ac9c72be5b/ijms-26-08167-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/84ebcbc1ff04/ijms-26-08167-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/ccdb53a31922/ijms-26-08167-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/f21280b38aa9/ijms-26-08167-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/11ac9c72be5b/ijms-26-08167-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/4d94/12427784/84ebcbc1ff04/ijms-26-08167-g001.jpg

相似文献

1
Regioselective Synthesis of 5-Substituted 3-(β-d-Glycopyranosyl)isoxazoles and -isoxazolines by 1,3-Dipolar Cycloaddition as Potential Anticancer Agents and Glycogen Phosphorylase Inhibitors.通过1,3-偶极环加成反应区域选择性合成5-取代的3-(β-D-吡喃葡萄糖基)异恶唑和异恶唑啉作为潜在抗癌剂和糖原磷酸化酶抑制剂。
Int J Mol Sci. 2025 Aug 22;26(17):8167. doi: 10.3390/ijms26178167.
2
Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition.葡萄糖衍生的螺异恶唑啉是通过抑制糖原磷酸化酶来对抗2型糖尿病的抗高血糖药物。
Eur J Med Chem. 2016 Jan 27;108:444-454. doi: 10.1016/j.ejmech.2015.12.004. Epub 2015 Dec 10.
3
Synthesis of heterocyclic N-(β-D-glucopyranosyl)carboxamides for inhibition of glycogen phosphorylase.杂环 N-(β-D-吡喃葡萄糖基)羧酰胺的合成及其对糖原磷酸化酶的抑制作用。
Carbohydr Res. 2012 Apr 1;351:56-63. doi: 10.1016/j.carres.2012.01.020. Epub 2012 Jan 31.
4
Prescription of Controlled Substances: Benefits and Risks管制药品的处方：益处与风险
5
Platinum-group metal half-sandwich complexes of sugar-isoxazol(in)e conjugates - synthesis and evaluation of their antineoplastic and antimicrobial activities.糖异恶唑（啉）共轭物的铂族金属半夹心配合物——其抗肿瘤和抗菌活性的合成与评价
Eur J Pharm Sci. 2025 Sep 5:107260. doi: 10.1016/j.ejps.2025.107260.
6
Design, evaluation, cytotoxic activity, molecular docking, ADMET analysis, and dynamic simulations and the preparation of new isoxazoles, thiazoles, 1,3-thiazines, and thiazolopyrimidines derived from quinoline-pyridopyrimidines.喹啉-吡啶并嘧啶衍生的新型异恶唑、噻唑、1,3-噻嗪和噻唑并嘧啶的设计、评估、细胞毒性活性、分子对接、ADMET分析、动态模拟及制备
Pharm Biol. 2025 Dec;63(1):607-644. doi: 10.1080/13880209.2025.2547744. Epub 2025 Aug 19.
7
Design and Synthesis of 3-(β-d-Glucopyranosyl)-4-amino/4-guanidino Pyrazole Derivatives and Analysis of Their Glycogen Phosphorylase Inhibitory Potential.设计与合成 3-(β-d-吡喃葡萄糖基)-4-氨基/4-胍基吡唑衍生物及其对糖原磷酸化酶抑制潜力的分析。
Molecules. 2023 Mar 28;28(7):3005. doi: 10.3390/molecules28073005.
8
Recent advances in the application of the isoxazoline route to aldols in the synthesis of natural products.异恶唑啉路线在天然产物合成中用于醛醇缩合反应的最新进展。
Nat Prod Rep. 2025 May 22;42(5):876-910. doi: 10.1039/d4np00069b.
9
Design, synthesis, and biological evaluation of 5-(1H-indol-5-yl)isoxazole-3-carboxylic acids as novel xanthine oxidase inhibitors.设计、合成及 5-(1H-吲哚-5-基)异恶唑-3-羧酸类化合物作为新型黄嘌呤氧化酶抑制剂的生物评价。
Eur J Med Chem. 2024 May 5;271:116443. doi: 10.1016/j.ejmech.2024.116443. Epub 2024 Apr 26.
10
Synthesis, characterization and biological evaluation of some novel 17-isoxazoles in the estrone series.雌酮系列中一些新型 17-异恶唑的合成、表征及生物评价。
Steroids. 2012 Sep;77(11):1075-85. doi: 10.1016/j.steroids.2012.05.003. Epub 2012 May 18.

本文引用的文献

1
Half sandwich-type osmium, ruthenium, iridium and rhodium complexes with bidentate glycosyl heterocyclic ligands induce cytostasis in platinum-resistant ovarian cancer cells and bacteriostasis in Gram-positive multiresistant bacteria.具有双齿糖基杂环配体的半夹心型锇、钌、铱和铑配合物可诱导铂耐药卵巢癌细胞的细胞生长停滞以及革兰氏阳性多重耐药细菌的抑菌作用。
Front Chem. 2023 Jan 30;11:1086267. doi: 10.3389/fchem.2023.1086267. eCollection 2023.
2
Dual-Target Compounds against Type 2 : Proof of Concept for Sodium Dependent Glucose Transporter (SGLT) and Glycogen Phosphorylase (GP) Inhibitors.针对2型糖尿病的双靶点化合物：钠依赖性葡萄糖转运蛋白（SGLT）和糖原磷酸化酶（GP）抑制剂的概念验证
Pharmaceuticals (Basel). 2021 Apr 15;14(4):364. doi: 10.3390/ph14040364.
3
(Guanidine)copper Complex-Catalyzed Enantioselective Dynamic Kinetic Allylic Alkynylation under Biphasic Condition.（胍）铜配合物催化的双相条件下对映选择性动态动力学烯丙基炔基化反应
J Am Chem Soc. 2018 Jul 11;140(27):8448-8455. doi: 10.1021/jacs.7b12806. Epub 2018 Jun 26.
4
Glycogen phosphorylase inhibition improves beta cell function.糖原磷酸化酶抑制可改善β细胞功能。
Br J Pharmacol. 2018 Jan;175(2):301-319. doi: 10.1111/bph.13819. Epub 2017 Jun 18.
5
C-Glycopyranosyl Arenes and Hetarenes: Synthetic Methods and Bioactivity Focused on Antidiabetic Potential.C-糖基芳基化合物和杂芳基化合物：合成方法和以抗糖尿病潜力为重点的生物活性。
Chem Rev. 2017 Feb 8;117(3):1687-1764. doi: 10.1021/acs.chemrev.6b00475. Epub 2017 Jan 25.
6
Accurate quantification of apoptosis progression and toxicity using a dielectrophoretic approach.利用介电泳方法准确量化细胞凋亡进程和毒性。
Analyst. 2016 Nov 14;141(23):6408-6415. doi: 10.1039/c6an01596d.
7
4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase.4(5)-芳基-2-C-吡喃葡萄糖基-咪唑类化合物作为新型纳摩尔级糖原磷酸化酶葡萄糖类似物抑制剂
ACS Med Chem Lett. 2015 Oct 19;6(12):1215-9. doi: 10.1021/acsmedchemlett.5b00361. eCollection 2015 Dec 10.
8
Synthesis of C-xylopyranosyl- and xylopyranosylidene-spiro-heterocycles as potential inhibitors of glycogen phosphorylase.作为糖原磷酸化酶潜在抑制剂的C-吡喃木糖基和亚甲基吡喃木糖基螺杂环的合成。
Carbohydr Res. 2014 Nov 18;399:38-48. doi: 10.1016/j.carres.2014.05.020. Epub 2014 Jun 4.
9
Glycogen phosphorylase inhibitor N-(3,5-dimethyl-Benzoyl)-N'-(β-D-glucopyranosyl)urea improves glucose tolerance under normoglycemic and diabetic conditions and rearranges hepatic metabolism.糖原磷酸化酶抑制剂 N-(3,5-二甲基苯甲酰基)-N'-(β-D-吡喃葡萄糖基)脲在正常血糖和糖尿病条件下改善葡萄糖耐量，并重新排列肝脏代谢。
PLoS One. 2013 Jul 25;8(7):e69420. doi: 10.1371/journal.pone.0069420. Print 2013.
10
Hypoiodite mediated synthesis of isoxazolines from aldoximes and alkenes using catalytic KI and Oxone as the terminal oxidant.次碘酸盐介导的醛肟和烯烃合成异噁唑啉反应，使用催化碘化钾和过氧单磺酸钾作为末端氧化剂。
Chem Commun (Camb). 2013 May 25;49(42):4800-2. doi: 10.1039/c3cc41164h.