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用于合成4,4'-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物和1,4-二氢吡喃并[2,3-c]吡唑的聚(苯胺-三聚氰胺)@MnFeO纳米催化剂及其抗氧化和抗癌活性评估

Poly(aniline--melamine)@MnFeO nanocatalyst for the synthesis of 4,4'-(arylmethylene) bis (1H-pyrazole-5-ol) derivatives, and 1,4- dihydropyrano[2,3-]pyrazoles and evaluation of their antioxidant, and anticancer activities.

作者信息

Mirani Nezhad Shefa, Pourmousavi Seied Ali, Nazarzadeh Zare Ehsan, Heidari Golnaz, Manoochehri Hamed, Sharifi Esmaeel

机构信息

School of Chemistry, Damghan University, Damghan, Iran.

Research Center for Molecular Medicine, Hamadan University of Medical Sciences, Hamadan, Iran.

出版信息

Front Chem. 2022 Oct 28;10:1046120. doi: 10.3389/fchem.2022.1046120. eCollection 2022.

Abstract

In this work, magnetic poly(aniline--melamine) nanocomposite as an efficient heterogeneous polymer-based nanocatalyst was fabricated in two steps. First, poly(aniline--melamine) was synthesized through the chemical oxidation by ammonium persulfate, then the magnetic nanocatalyst was successfully prepared from the coprecipitation method in the presence of poly(aniline--melamine). The resulting poly(aniline--melamine)@MnFeO was characterized by FTIR, FESEM, XRD, VSM, EDX, TGA, and UV-vis analyses. The catalytic activity of poly(aniline--melamine)@MnFeO was investigated in the synthesis of 4,4'-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives, and new alkylene bridging bis 4,4'-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives in excellent yields. The yield of 1,4-dihydropyrano[2,3-c]pyrazoles, 4,4'-(arylmethylene)bis(1H-pyrazol-5-ol), yields, and new alkylene bridging bis 4,4'-(arylmethylene)bis(1H-pyrazol-5-ol) derivatives were obtained 89%-96%, 90%-96%, and 92%-96%, respectively. The poly(aniline--melamine)@MnFeO nanocatalyst can be recycled without pre-activation and reloaded up to five consecutive runs without a significant decrease in its efficiency. In addition, the antioxidant activity of some derivatives was evaluated by DPPH assay. Results showed that the maximum antioxidant activity of 4,4'-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives and 1,4-dihydropyrano[2,3-]pyrazoles were 75% and 90%, respectively. Furthermore, 4,4'-(arylmethylene)bis(1H-pyrazole-5-ol) derivatives and 1,4-dihydropyrano[2,3-]pyrazoles showed good potential for destroying colon cancer cell lines. Consequently, the poly(aniline--melamine)@MnFeO nanocomposite is an excellent catalyst for green chemical processes owing to its high catalytic activity, stability, and reusability.

摘要

在本研究中,通过两步法制备了磁性聚(苯胺 - 三聚氰胺)纳米复合材料作为一种高效的非均相聚合物基纳米催化剂。首先,通过过硫酸铵化学氧化合成聚(苯胺 - 三聚氰胺),然后在聚(苯胺 - 三聚氰胺)存在下,采用共沉淀法成功制备磁性纳米催化剂。通过傅里叶变换红外光谱(FTIR)、场发射扫描电子显微镜(FESEM)、X射线衍射(XRD)、振动样品磁强计(VSM)、能谱仪(EDX)、热重分析(TGA)和紫外可见光谱(UV-vis)分析对所得的聚(苯胺 - 三聚氰胺)@MnFeO进行了表征。研究了聚(苯胺 - 三聚氰胺)@MnFeO在合成4,4'-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物以及新型亚烷基桥联双4,4'-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物中的催化活性,产率优异。1,4-二氢吡喃并[2,3-c]吡唑、4,4'-(芳基亚甲基)双(1H-吡唑-5-醇)以及新型亚烷基桥联双4,4'-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物的产率分别为89% - 96%、90% - 96%和92% - 96%。聚(苯胺 - 三聚氰胺)@MnFeO纳米催化剂无需预活化即可循环使用,并且可以连续重复使用多达五次,而其效率没有显著降低。此外,通过DPPH法评估了一些衍生物的抗氧化活性。结果表明,4,4'-(芳基亚甲基)双(1H-吡唑-5-醇)衍生物和1,

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1c5c/9649443/fef64b8de487/fchem-10-1046120-g001.jpg

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