ABSTRACT
Schiff bases are organic compounds containing carbon nitrogen double bond –CH=N- with enormous importance due to their structural chemistry (-CH=N-). This study was designed to synthesize and characterise some Schiff bases derived from Quercetin and examine their antibacterial activities. The two Schiff bases were synthesised using conventional method by refluxing ethanolamine and thiourea with Quercetin. The compounds were characterized with UV/vis and FT-IR spectroscopy and subjected to in vitro antibacterial screening using disc diffusion techniques on selected bacterial species. The wavelength of maximum absorption showed 1.757 and 1.650 for AQ-1, and AQ-2 respectively, while the infrared absorption for the imine (1576-1888 cm-1) carbonyl (1608-1722 cm-1) and hydroxy (3201-3365 cm-1) groups were observed in all the synthesized compounds. The antibacterial activity showed that AQ2 had the highest zone of inhibition (30 mm) against E. coli with minimum inhibitory concentration (MIC) of 12.5 µg/ml. This indicates that AQ is effective as antibacterial agent. The results obtained have shown the efficiency of the Schiff bases as potential antibacterial molecules for development of antibacterial drugs.
Table of Contents
DECLARATION ii
CERTIFICATION iii
DEDICATION iv
ACKNOWLEDGMENTS v
ABSTRACT 1
CHAPTER ONE
1.0 INTRODUCTION
1.1 Background of the Study 3
1.2 Synthetic Modification of Organic Compounds. 5
1.2.1 The Significance of Synthetic Modification: 5
1.9 Statement of Research Problem 12
1.10 Justification for research 13
CHAPTER TWO
2.0 BRIEF LITERATURE REVIEW
2.1 Method of Schiff Base synthesis 13
CHAPTER THREE
3.0 MATERIALS AND METHODS
3.1 Materials 25
3.2 Reagents 26
3.2.1 Synthesis of Quercetin Thiourea 26
3.4 Antibacterial activity 28
3.3.1 In vitro antibacterial screening 28
3.3.2 Minimum inhibitory concentration (MIC) 29
3.3.3 Minimum Bactericidal Concentration (MBC) 30
CHAPTER FOUR
4.0 RESULTS AND DISCUSSION
Table 1: Chemical data of synthesised compounds 31
KEY; AQ1: Quercetin Thiourea, AQ2: Quercetin Ethanolamine 31
KEY; AQ1: Quercetin Thiourea, AQ2: Quercetin Ethanolamine 32
Table 3: Table of Antimicrobial screening 32
4.2 DISCUSSIONS 35
4.2.1 Synthesis and characterization 35
4.2.2 ANTIMICROBIAL ACTIVITY 36
CHAPTER FIVE
5.0 CONCLUSION AND RECOMMENDATION
5.1 CONCLUSION 38
5.2 RECOMMENDATION 38
REFERENCES 39
APPENDIX 1 42
CHAPTER ONE
1.0 INTRODUCTION
1.1 Background of the Study
Quercetin is a natural polyphenolic compound found abundantly in fruits, vegetables, and various plant-based foods. It belongs to the flavonoid class of compounds and has garnered significant attention in recent years due to its numerous health-promoting properties (Smith, 2021). Quercetin is known for its antioxidant, anti-inflammatory, and anticancer activities, making it a subject of interest in the fields of medicine, nutrition, and pharmaceuticals.
The potential therapeutic benefits of quercetin have sparked research aimed at enhancing its bioavailability and pharmacological activity. One promising avenue for achieving this is the synthetic modification of quercetin using various chemical reagents. Among these reagents, thiourea and ethanolamine have emerged as notable candidates for modifying quercetin's chemical structure (Smith, 2021).
Thiourea is a well-known compound in synthetic chemistry, valued for its versatile reactivity and ability to introduce functional groups into organic molecules. Ethanolamine, on the other hand, is a compound that contains both an amine and an alcohol functional group, making it suitable for reactions that involve nucleophilic substitution and the formation of new chemical bonds (Johnson, 2019).
The synthetic modification of quercetin with thiourea and ethanolamine offers the potential to create novel quercetin derivatives with improved bioavailability and enhanced pharmacological properties. These modified compounds may find applications in drug development, where the optimization of quercetin's bioactivity could lead to new therapeutic agents for various medical conditions.
Given the significance of quercetin as a natural bioactive compound and the potential benefits of synthetic modification, this study aims to explore the reactions of quercetin with thiourea and ethanolamine in detail. The research seeks to elucidate the mechanisms of these reactions, characterize the resulting compounds, and assess their potential pharmacological activities. Ultimately, this investigation contributes to the growing body of knowledge on quercetin and its synthetic derivatives, with implications for drug discovery and the development of health-promoting compounds (Anderson, 2018).
1.2 Synthetic Modification of Organic Compounds.
Synthetic modification, also known as chemical modification or functionalization, is a fundamental aspect of organic chemistry and materials science. It involves the deliberate alteration of a molecule's chemical structure to introduce specific functional groups or properties. Synthetic modification plays a pivotal role in various fields, including pharmaceuticals, materials science, and chemical engineering. This section provides an introductory overview of synthetic modification and its importance in the context of your study on the modification of quercetin with thiourea and ethanolamine.
1.2.1 The Significance of Synthetic Modification:
Synthetic modification serves as a powerful tool for tailoring the properties of molecules to meet specific needs and applications. It allows chemists to enhance the functional characteristics of existing compounds or create entirely new compounds with desired attributes. In the case of quercetin, synthetic modification holds the promise of optimizing its pharmacological activity and bioavailability, potentially expanding its applications in medicine and related fields (Brown, 2017).
1.2.2 Methods of Synthetic Modification:
There are numerous methods and reagents available for synthetic modification, ranging from simple chemical reactions to more complex organic synthesis strategies. Common techniques include acylation, alkylation, esterification, amidation, and nucleophilic substitution reactions, among others. Each method has its own set of advantages and limitations, and the choice of method depends on the specific goals of the modification.
1.2.3 Applications of Synthetic Modification:
Synthetic modification finds applications in various industries and disciplines:
Pharmaceuticals: In drug development, synthetic modification is employed to improve the pharmacokinetics and pharmacodynamics of compounds, enhancing their therapeutic efficacy and reducing potential side effects.
Materials Science: In materials science, chemical modification is used to enhance the properties of polymers, composites, and other materials, tailoring them for specific applications such as electronics, coatings, and biomaterials.
Chemical Engineering: Chemical engineers use synthetic modification to optimize industrial processes, increase the efficiency of chemical reactions, and design novel chemical products.
Environmental Science: Chemical modification can be applied to environmental remediation by designing compounds that capture pollutants or enhance the degradation of contaminants.
1.3 Quercetin: A Natural Polyphenol
Quercetin is a naturally occurring polyphenolic compound belonging to the flavonoid group, a class of secondary metabolites found in various plants. It is widely distributed in fruits, vegetables, leaves, and grains, making it a common dietary constituent. Quercetin has gained considerable attention in the fields of nutrition, medicine, and pharmaceuticals due to its diverse biological activities and potential health benefits (Wilson, 2020).
Chemical Structure and Properties:
Quercetin is characterized by its distinctive chemical structure, featuring a flavonoid core with multiple phenolic rings and hydroxyl groups. The chemical formula of quercetin is C₁₅H₁₀O₇, and its molecular weight is approximately 302.24 g/mol. The compound exists in several naturally occurring forms, including quercetin aglycone and various glycosides, where sugar molecules are attached to the quercetin backbone.
Fig; Structure of Quercetin
Biological Activities:
Quercetin is renowned for its remarkable biological activities, including:
Antioxidant Properties: Quercetin is a potent antioxidant that can neutralize harmful free radicals and reactive oxygen species (ROS). This antioxidant capacity contributes to its potential protective role against oxidative stress-related diseases.
Anti-Inflammatory Effects: Quercetin exhibits anti-inflammatory properties by inhibiting inflammatory mediators and pathways. It may help reduce chronic inflammation, which is associated with various chronic diseases.
Anticancer Potential: Some studies suggest that quercetin may have anticancer properties by interfering with the growth and proliferation of cancer cells and promoting apoptosis (cell death), (Brown, 2017).
Cardiovascular Health: Quercetin is linked to cardiovascular health due to its ability to improve endothelial function, reduce blood pressure, and lower the risk of heart disease.
Immune System Support: Quercetin may enhance immune system function by modulating immune responses and suppressing allergic reactions.
Neuroprotective Effects: Emerging research indicates that quercetin may have neuroprotective properties, potentially reducing the risk of neurodegenerative diseases.
Dietary Sources: Quercetin is abundant in a wide range of foods, including apples, onions, citrus fruits, berries, tea, and leafy greens. Its presence in the diet is associated with potential health benefits, and it is often included in discussions about the health-promoting aspects of a balanced and plant-rich diet.
Bioavailability and Pharmacokinetics: While quercetin offers numerous health advantages, its bioavailability can be limited in some cases due to factors like poor solubility and rapid metabolism. This challenge has prompted research into methods to improve quercetin's bioavailability, including synthetic modification, which can enhance its pharmacological properties.
Understanding the natural occurrence, properties, and bioactivities of quercetin lays the foundation for exploring its synthetic modification, which aims to optimize its potential for pharmaceutical and biomedical applications. The next sections of your study will delve into the specific synthetic reactions involving quercetin, thiourea, and ethanolamine, shedding light on how these modifications may impact the compound's properties and bioactivities (Brown, 2017).
1.4 Importance of Quercetin in Pharmaceuticals
Quercetin, a naturally occurring polyphenolic compound, holds significant importance in the field of pharmaceuticals due to its diverse pharmacological properties and potential therapeutic applications. Its multifaceted benefits have made it a subject of interest for drug development and biomedical research. Here, we explore the crucial role of quercetin in pharmaceuticals:
1. Antioxidant Activity: Quercetin is a potent antioxidant with the ability to scavenge free radicals and reduce oxidative stress. Oxidative stress is implicated in various chronic diseases, including cardiovascular diseases, neurodegenerative disorders, and cancer. By neutralizing free radicals, quercetin may contribute to the prevention and treatment of oxidative stress-related conditions.
2. Anti-Inflammatory Properties: Chronic inflammation is at the core of many diseases, and quercetin exhibits anti-inflammatory effects by inhibiting inflammatory mediators and pathways. This anti-inflammatory activity can be valuable in conditions such as arthritis, allergies, and inflammatory bowel diseases.
3. Anticancer Potential: Quercetin has shown promise in cancer prevention and treatment. It can interfere with cancer cell growth and proliferation, induce apoptosis (programmed cell death), and inhibit angiogenesis (the formation of blood vessels that feed tumors). Research suggests that quercetin may have potential applications as an adjuvant therapy in cancer treatment.
4. Cardiovascular Health: Quercetin's cardiovascular benefits include improving endothelial function, reducing blood pressure, and lowering the risk of heart disease. It may help protect against atherosclerosis by inhibiting the oxidation of low-density lipoprotein (LDL) cholesterol and reducing inflammation in blood vessels.
In summary, quercetin's versatility as a natural compound with antioxidant, anti-inflammatory, anticancer, cardiovascular, immunomodulatory, neuroprotective, and antiviral properties positions it as a promising component in pharmaceutical research and development. Its potential to mitigate a wide range of health conditions makes it a valuable asset in the quest for novel therapeutic agents and improved pharmaceutical formulations. As such, your study on the synthetic modification of quercetin with thiourea and ethanolamine may contribute to harnessing its pharmaceutical potential further (Garcia, 2019).
1.7 Aim of Research
The primary aim of this study is to investigate and characterize the synthetic modification of quercetin through reactions with thiourea and ethanolamine. This research aims to elucidate the mechanisms, intermediates, and outcomes of these modifications, with a specific focus on understanding how they influence quercetin's chemical structure and potential bioactivities.
1.8 Objectives for Research
The objective of the research was to;
I. Synthesize quercetin derivatives through reactions with thiourea and ethanolamine.
II. Characterize the compounds synthesized using UV-Visible and FT-IR Spectroscopy.
III. Assess the potential antimicrobial properties of the modified quercetin compounds.
1.9 Statement of Research Problem
The research aims to investigate the potential health benefits and mechanisms of action of quercetin, despite numerous studies suggesting its antioxidant, anti-inflammatory, and anti-cancer properties, there is a need for a comprehensive understanding of the specific pathways and molecular interactions through which quercetin exerts its effects. Additionally, exploring the bioavailability and optimal dosage of quercetin for therapeutic applications is essential for translating its potential into practical health interventions. This research seeks to address these gaps in knowledge and contribute to the development of evidence-based recommendations for the utilization of quercetin in promoting human health.
1.10 Justification for research
This research on quercetin aims to uncover its health benefits and mechanisms of action, with its potential to impact conditions like cancer and cardiovascular diseases, understanding quercetin's therapeutic potential is crucial. The findings could have significant public health implications, this study addresses key knowledge gaps in the field, paving the way for advancements in nutrition and health.
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