Synthesis and antimicrobial activity of branched benzoxazinophenothiazines and their derivatives

Project Abstract

Benzoxazinophenothiazines and their derivatives have gained significant attention due to their diverse pharmacological activities, especially their antimicrobial properties. In this study, a series of branched benzoxazinophenothiazines and their derivatives were synthesized using efficient synthetic routes. The structures of the compounds were confirmed using spectroscopic techniques such as NMR, IR, and mass spectrometry. The antimicrobial activity of these compounds was evaluated against a panel of pathogenic microorganisms including bacteria and fungi. The results demonstrated that the synthesized branched benzoxazinophenothiazines and their derivatives exhibited promising antimicrobial activity. Some of the compounds showed potent inhibitory effects against both Gram-positive and Gram-negative bacteria. Furthermore, certain derivatives displayed significant antifungal activity against various fungal strains. The structure-activity relationship analysis revealed that the substitution pattern on the benzoxazinophenothiazine core significantly influenced the antimicrobial potency of the compounds. Mechanistic studies suggested that the antimicrobial activity of these compounds may be attributed to their ability to disrupt microbial cell membranes and interfere with essential cellular processes. Additionally, the compounds showed low cytotoxicity towards mammalian cells, indicating their potential for further development as antimicrobial agents. Further investigations into the mode of action and toxicity profiles of these compounds are warranted to fully elucidate their therapeutic potential. Overall, this study highlights the synthesis of novel branched benzoxazinophenothiazines and their derivatives as promising antimicrobial agents. The compounds exhibited potent activity against a wide range of pathogenic microorganisms, making them potential candidates for the development of new antimicrobial drugs. The findings of this research contribute to the growing body of knowledge on benzoxazinophenothiazines and their derivatives as effective antimicrobial agents, paving the way for future studies aimed at optimizing their pharmacological properties and therapeutic applications.

Project Overview

<p> Title page – – – – – – – – – – – i<br>Approval Page- – – – – – – – – – – ii<br>Certification – – – – – – – – – – – iii<br>Dedication – – – – – – – – – – – iv<br>Acknowledgment – – – – – – – – – – v<br>Abstract – – – – – – – – – – – vi<br>Table of contents – – – – – – – – – -vii<br>List of Figures- – – – – – – – – – -viii<br>List of Abbreviations – – – – – – – – – – x<br>List of Tables – – – – – – – – – – -xi<br>CHAPTER ONE: INTRODUCTION<br>1.1 Background of study – – – – – – – – – 1<br>1.2 Statement of the Problem – – – – – – – – 4<br>1.3 Objectives of the Study – – – – – – – – 5<br>1.4 Justification of the Study – – – – – – – – 5<br>CHAPTER TWO: LITERATURE REVIEW<br>2.0 Linear Phenothiazine – – – – – – – – – 6<br>2.1 Synthesis of Triazaphenothiazine – – – – – – – 7<br>2.2 Synthesis of Tetraazaphenothiazine – – – – – – – 9<br>2.3 Angular Phenothiazine – – – – – – – -10<br>viii<br>2.4 Aza Analogue of Angular phenothiazine – – – – – -13<br>2.5 Linear Phenoxazine – – – – – – – – – 18<br>2.6 Angular Phenoxazine – – – – – – – – – 19<br>2.7 Aza- Analogue of Angular Phenoxazine – – – – – -23<br>2.8 Branched phenothiazine and Phenoxazine Compounds – – – – 27<br>CHAPTER THREE: EXPERIMENTAL<br>3.0 General Information – – – – – – – – – 35<br>3.1 6-Chloro-10-nitro-5H-benzo[a]phenoxazin-5-one – – – – – 35<br>3.2 14- Nitrobenzo[a][1,4]benzoxazino[3,2,-c]phenothiazine – – – -36<br>3.3 11-Amino-6-Chloro-9-thiol-8,10-diazabenzo[a]phenoxazin-5-one – – – 37<br>3.4 15-Amino-13-thiol-12,14-diazabenzo[a][1,4]benzoxazino[3,2- c]phenothiazine – 37<br>3.5 6,8-Dichlorobenzo[a]phenoxazin-5-one – – – – – – 38<br>3.6 12-Chloro-9-methoxy-8-azabenzo[a][1,4]benzoxazino[3,2-c]phenothiazine – 38<br>3.7 Antimicrobial Activity – – – – – – – – 39<br>3.8 Sensitivity testing of compounds – – – – – – – 39<br>3.9 Minimum inhibitory concentration testing of compounds – – – – 40<br>CHAPTER FOUR: RESULTS AND DISCUSSION<br>4.1 6-Chloro-10-nitro-5H-benzo[a]phenoxazin-5-one – – – – – 41<br>4.2 11-Amino-6-Chloro-9-thiol-8,10-diazabenzo[a]phenoxazin-5-one – – -44<br>4.3 6,8-Dichlorobenzo[a]phenoxazin-5-one – – – – – – 47<br>4.4 Result of Antimicrobial Sensitivity Test – – – – – – 50<br>ix<br>4.5 Minimum inhibitory Concentration Determination – – – – – 51<br>4.6 Result of Minimum Inhibitory Concentration – – – – – 52<br>CHAPTER FIVE<br>Conclusion – – – – – – – – – – – 53<br>References – – – – – – – – – – – 54 <br></p>