Synthesis of Heterocyclic and Non-heterocyclic Compounds Derived from Novel 2-Furanones and Evaluation of their Anti-viral Activity

Hend El-Shanbaky,Mosad Mohamed,Rania Abd El-Hameed

doi:10.21608/aprh.2020.49788.1120

Hend El-Shanbaky, Mosad Mohamed + Show 1 more

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https://doi.org/10.21608/aprh.2020.49788.1120

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Abstract

Objective: The aim of the present study is to synthesize novel 2-furanones due to their biological activities and also their ability to be converted to several biologically active heterocyclic and non-heterocyclic compounds. Methods: Two novel 2-furanone derivatives were synthesized and used to prepare fourteen heterocyclic and non-heterocyclic compounds. Structures of all the newly synthesized compounds were confirmed by elemental and spectral analysis including Mass, IR and 1H-NMR spectroscopy. Evaluation of antiviral activity of selected examples of the obtained compounds was performed using two gastroenteric viruses: adenovirus and rotavirus. Results: Two pyridazinone derivatives namely; 3-(3,4-Dichlorophenyl)-5-[(2-methoxypheny)l-methyl]-1H-pyridazin-6-one (7a) and 3-(3,4-Dichlorophenyl)-5-[(4-fluropheny)l-methyl]-1H-pyridazin-6-one (7b) showed high activities against rotavirus. Conclusions: Compounds 7a and 7b can be considered as promising anti-rotaviral agents needing further investigations and clinical studies.

Highlights

Viruses are from the prime causes of diseases worldwide; viral gastroenteritis is a serious viral infection which affects millions of individuals around the world, most of them are children
All melting points were uncorrected and measured using Electro-thermal IA 9100 apparatus (Shimadzu, Japan); IR spectra were recorded as potassium bromide pellets on a Perkin-Elmer 1650 spectrophotometer (USA), Faculty of Science, Cairo University, Cairo, Egypt. 1HNMR spectra were determined on a Varian Mercury (300 MHz) spectrometer (Varian UK) and chemical shifts were expressed as ppm against TMS as internal reference (The Main Chemical warfare Laboratories, Almaza, Cairo, Egypt)
With ammonium acetate; pyrrol-2-one derivatives 3a,b were produced. 4-Oxo-butanamides 4a,b were synthesized by refluxing 2-furanones 2a,b with benzyl amine and 1-phenyl-pyridazinone 5a,b were prepared from 2-furanones by refluxing with phenyl hydrazine according to the reported procedure [19,21]

Summary

Introduction

Viruses are from the prime causes of diseases worldwide; viral gastroenteritis is a serious viral infection which affects millions of individuals around the world, most of them are children. The infection may occur due to different viruses, for example, coxsackievirus, adenovirus, and rotavirus. Rotavirus is the leading cause of severe gastroenteritis in the pediatric population worldwide 3 adenovirus is the second most common virus causing gastroenteritis in young children,[4] and coxsackievirus is considered the least dangerous cause of gastroenteritis among the three viruses 5. 2-Furanones; well-known heterocyclic derivatives; had attracted a great attention during the last decade due to facile ring opening and conversion to other heterocycles; pyrrolones, pyridazinones, pyrazoles and oxadizoles. These heterocycles acquired an obvious medicinal interest as antimicrobial 6-8, anti-inflammatory 8-16, antimycobacterial 18,19 and anti-cancer agents 20-22

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