Studies on Benzoxazine Derivaties

Abstract

The 5, 6, 7 trimethoxy (1, 4) benzoxazine -2,3diones was synthesized by reaction of 2-amino-3,4,5 trimethoxyphenol with oxalyl chloride. The new compound of benzoxazine derivative was characterized by elemental analysis, mass spectroscopy , infrared and 1H-NMR . The compound exhibited antifungal and antibacterial activities.

Introduction

I. INTRODUCTION

In recent years benzoxazine derivatives containing nitrogen have attracted increased attention due to the broad spectrum of their biological activities {1} like antibacterial {2,3}antifungal {4}  

Benzoxazines show a wide range of biological activity which are key molecules for the synthesis of various pharmaceutical agents as antifungal [5], antimicrobial [6]. There are only few reports suggesting the antimicrobial properties of benzoxazine derivatives so for [7,8]. Benzoxazine derivatives also display various biological activities such as anticancer [9], antimicrobial [10], antifungi [11], antiplatelet [12], and antituberculosis activities [13].

II. EXPERIMENTAL PART

A. Instrumentation

All melting points were measured on a Gallenkamp melting apparatus and uncorrted.The IR spectra of compounds were recorded on shimadzu IR Affinity FTIR spectrophotometer using KBr discs and the values are expressed in???? cm-1. The 1H-NMR spectra of compound were recorded on Bruker Avance 400 MHz NMR spectrophotometer using DMSO as an internal standard and the values are expressed in ???? ppm. The elemental analyasis of the compounds were recorded on a perkin – Elmer 2400 CHN elemental analyzer.

The mass spectra were recorded on a GCMS-QP-1000EX mass spectrometer at (70ev) Synthesis of 5, 6, 7 trimethoxy {1, 4} benzoxazine -2, 3 diones: In around bottom flask 250ml dissolve (16,3gm,0.1mole) of 2-amino-3,4,5 trimethoxyphenol in 100ml ethanol then add (12,6gm,0.1mole) of oxalyl chloride, stirr the mixture at room temperature for 2hrs then add 2ml of piperidine. The mixture was heated to reflux for 10hrs and keep overnight. The solide was separated by filtration. The solid was recrystallized from ethanol.

III. RESULTS AND DISCUSSION

Spectrscpic studies of 5, 6, 7 trimethoxy (1, 4) benzoxazine –

2, 3 diones : The infrared spectrum of  table (2) displayed a strong band at 1665cm-1 corresponding to ? (C=O) (lactone),as well as the IR spectrum exhibited absorption band at 3218cm-1 due to (N- H). the 1H-NMR spectrum of the (2) in deuterated DMSO-d6 table (2)exhibited from low field to high field, the following signals (???? /ppm): 8,13(S,H,NH),7,65(S,1H,Ar- H)and 3,81(3S,9H,3OCH3). The mass spectrum of compound (1) exhibited the molecular ion peak [M]+ at m/e 253 (67%) indicating the molecular formula C11H11NO6, beside other fragemnts which are in accordance with the proposed structure 238(44%), 223(45%), 193(71%),163(80%),149(93%).77(100%).

A. Biological Activity

Measurement of antimicrobial activity using diffusion disc method: Antibacterial and antifungal activities of some synthesized compound was screened using the disc diffusion method. All the tested compounds showed antibacterial and antifungal activity and these activities were compared to standard amoxicillin, the results of antimicrobial studies are given in table 3, the antimicrobial activity of newly synthesized benzoxazine was conducted against gram positive and gram negative groups namely staphylococcus aureus and Escherichia coli respectively as well as Aspergillus flavus and candida albicans as tested fungi by disc diffusion method. Amoxicillin was employed as reference standard to compare the results. Each test compare was dissolved in dimethyl sulphoxide (DMSO). The concentration of DMSO solutions was 0.1 mg/ml.

Table 1: Physical characterization of  benzoxazine derivative

Table 2: Spectroscopic for benzoxazine derivative

Table 3: The inhibition zone diameter of some benzoxazine derivative

References

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Copyright

Copyright © 2024 Mohamed Saad Muftah. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.