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磁性磺化多糖作为合成具有取代吡咯环的异恶唑-5-酮衍生物的高效催化剂,用作抗癌剂。

Magnetic sulfonated polysaccharides as efficient catalysts for synthesis of isoxazole-5-one derivatives possessing a substituted pyrrole ring, as anti-cancer agents.

作者信息

Ghasemi Zarrin, Amale Afsaneh Hamidian, Azizi Sajjad, Valizadeh Sepideh, Soleymani Jafar

机构信息

Department of Organic Chemistry and Biochemistry, Faculty of Chemistry, University of Tabriz Tabriz 5166614766 Iran

Pharmaceutical Analysis Research Center, Tabriz University of Medical Sciences Tabriz Iran.

出版信息

RSC Adv. 2021 Nov 17;11(58):36958-36964. doi: 10.1039/d1ra06472j. eCollection 2021 Nov 10.

Abstract

Four polysaccharides (chitosan, cellulose, starch, and pectin) were magnetized with magnetic iron oxide (FeO) and then sulfonated (except pectin) with chlorosulfonic acid. The obtained solid acids were used as a catalyst in three-component reactions between -substituted-2-formylpyrrole, hydroxylamine-hydrochloride, and β-keto esters for the synthesis of 4-(2-pyrrolyl) methylene-isoxazole-5-ones. The optimal catalyst system was selected and studied by IR, SEM, TEM and XRD methods. The diverse isoxazoline derivatives (obtained a mild and simple approach) were also fully characterized by spectroscopic methods and screened for anti-cancer activities against HT-29 and MCF-7 colon and breast cancer and HEK 293 normal cells. The results revealed interesting anti-cancer activities.

摘要

四种多糖(壳聚糖、纤维素、淀粉和果胶)用磁性氧化铁(FeO)进行磁化,然后(果胶除外)用氯磺酸进行磺化。所得固体酸用作催化剂,用于α-取代-2-甲酰基吡咯、盐酸羟胺和β-酮酯之间的三组分反应,以合成4-(2-吡咯基)亚甲基异恶唑-5-酮。通过红外光谱(IR)、扫描电子显微镜(SEM)、透射电子显微镜(TEM)和X射线衍射(XRD)方法选择并研究了最佳催化剂体系。还通过光谱方法对以温和且简单的方法获得的多种异恶唑啉衍生物进行了全面表征,并针对HT-29和MCF-7结肠和乳腺癌以及HEK 293正常细胞筛选了抗癌活性。结果显示出有趣的抗癌活性。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d723/9043612/76f6d60c20b0/d1ra06472j-f1.jpg

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