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通过微波辐射下使用可重复使用的多相纳米催化剂的[3 + 2]环加成反应合成()-1-芳基-2-(1H-四唑-5-基)丙烯腈衍生物及其抗菌活性

Synthesis and Antimicrobial Activity of ()-1-Aryl-2-(1H-tetrazol-5-yl)acrylonitrile Derivatives via [3+2] Cycloaddition Reaction Using Reusable Heterogeneous Nanocatalyst under Microwave Irradiation.

作者信息

Nanda Ayashkanta, Kaur Navneet, Kaur Manvinder, Husain Fohad Mabood, Han Haesook, Bhowmik Pradip K, Sohal Harvinder Singh

机构信息

Medicinal and Natural Product Laboratory, Department of Chemistry, Chandigarh University, Gharuan, Mohali 140413, Punjab, India.

Department of Food Science and Nutrition, College of Food and Agriculture Sciences, King Saud University, Riyadh 11451, Saudi Arabia.

出版信息

Molecules. 2024 Sep 12;29(18):4339. doi: 10.3390/molecules29184339.

DOI:10.3390/molecules29184339
PMID:39339334
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11434072/
Abstract

The magnetically recoverable heterogeneous FeO@cellulose@Mn nanocomposite was synthesized by a stepwise fabrication of Mn nanoparticles on cellulose-modified magnetic FeO nanocomposites, and the morphology of the nanocomposite was characterized through advanced spectroscopic techniques. This nanocomposite was investigated as a heterogeneous catalyst for the synthesis of medicinally important tetrazole derivatives through Knoevenagel condensation between aromatic/heteroaromatic aldehyde and malononitrile followed by [3+2] cycloaddition reaction with sodium azide. Thirteen potent ()-1-aryl-2-(1H-tetrazol-5-yl)acrylonitrile derivatives are reported in this paper with very high yields (up to 98%) and with excellent purity (as crystals) in a very short period (3 min @ 120 W) using microwave irradiation. The present procedure offers several advantages over recent protocols, including minimal catalyst loading, quick reaction time, and the utilization of an eco-friendly solvent. Furthermore, the synthesized ()-1-aryl-2-(1H-tetrazol-5-yl)acrylonitrile derivatives (, , and ) are shown to have excellent resistance against various fungal strains over bacterial strains as compared to the standard drugs Cefixime (4 μg/mL) and Fluconazole (2 μg/mL).

摘要

通过在纤维素改性的磁性FeO纳米复合材料上逐步制备Mn纳米颗粒,合成了可磁回收的多相FeO@纤维素@Mn纳米复合材料,并通过先进的光谱技术对该纳米复合材料的形貌进行了表征。研究了这种纳米复合材料作为多相催化剂,通过芳族/杂芳族醛与丙二腈之间的Knoevenagel缩合反应,然后与叠氮化钠进行[3+2]环加成反应,合成具有重要药用价值的四唑衍生物。本文报道了13种有效的()-1-芳基-2-(1H-四唑-5-基)丙烯腈衍生物,使用微波辐射在很短的时间内(120W下3分钟)以非常高的产率(高达98%)和优异的纯度(作为晶体)获得。与最近的方案相比,本方法具有几个优点,包括催化剂负载量最低、反应时间短以及使用环保溶剂。此外,与标准药物头孢克肟(4μg/mL)和氟康唑(2μg/mL)相比,合成的()-1-芳基-2-(1H-四唑-5-基)丙烯腈衍生物(、和)对各种真菌菌株的抗性优于细菌菌株。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/99fe050a7137/molecules-29-04339-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/9705ec864ff8/molecules-29-04339-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/a4b3f3edc249/molecules-29-04339-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/f4be050faada/molecules-29-04339-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/567c7247c72e/molecules-29-04339-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/5a2fd69ed895/molecules-29-04339-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/fce023a5e99a/molecules-29-04339-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/0ace4a5c89e3/molecules-29-04339-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/99fe050a7137/molecules-29-04339-sch003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/9705ec864ff8/molecules-29-04339-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/a4b3f3edc249/molecules-29-04339-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/f4be050faada/molecules-29-04339-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/567c7247c72e/molecules-29-04339-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/5a2fd69ed895/molecules-29-04339-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/fce023a5e99a/molecules-29-04339-sch001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/0ace4a5c89e3/molecules-29-04339-sch002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/bfa2/11434072/99fe050a7137/molecules-29-04339-sch003.jpg

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