Chemistry of Biologically Potent Natural Products and Synthetic Compounds

Cover
Half-Title Page
Series Page
Title Page
Copyright Page
Contents
Preface
1 Medicinal Importance of Plant Metabolites
	1.1 Introductory Note
	1.2 Primary and Secondary Metabolites
	1.3 Functional Roles of Secondary Metabolites
	1.4 Source and Production of Secondary Metabolites
	1.5 Classification of Secondary Metabolic Substances
		1.5.1 Terpenes
		1.5.2 Phenol-Based Compounds
		1.5.3 Nitrogen-Containing Secondary Metabolites
			1.5.3.1 Alkaloids
		1.5.4 Secondary Metabolites Having Sulfur
	1.6 Bioactivity of Secondary Metabolites
		1.6.1 As Antioxidants
		1.6.2 As Antimicrobials
		1.6.3 As Anti-Diabetics Agents
	1.7 Conclusion and Future Perspectives
	References
2 Advances in Natural Products-Based Antiviral Agents
	2.1 Introduction
	2.2 Anti-HIV Agents
		2.2.1 Terpenes
		2.2.2 Phenylpropanoids
		2.2.3 Anthraquinones
		2.2.4 Alkaloids
	2.3 Natural Alkaloids With Activity Against HBV and HCV Infections
	2.4 Anti-Influenza Virus Agents
	2.5 Natural Products Active Against Herpesviruses
	2.6 Natural Products Against Chikungunya Virus
	2.7 Natural Products Targeting Dengue Virus
	2.8 Natural Products Targeting Coronaviruses
	2.9 Natural Products Against Other Viral Infections
	2.10 Conclusion
	Acknowledgements
	References
3 Bioactive Component of Black Pepper-Piperine: Structure-Activity Relationship and Its Broad-Spectrum Activity—An Overview
	List of Abbreviations
	3.1 Introduction: What is a Natural Product?
	3.2 Black Pepper
		3.2.1 Constituents of Black Pepper
		3.2.2 Major Alkaloids of Black Pepper
	3.3 Piperine—Active Molecule of Pepper
		3.3.1 Isolation of Piperine
		3.3.2 Piperine as Potential Drug
			3.3.2.1 Metabolism of Piperine
			3.3.2.2 Structure-Activity Relationship
			3.3.2.3 Piperine and Piperine Analogs
			3.3.2.4 Synergistic Activity of Piperine
	3.4 Overall Summary and Conclusion
	References
4 Chemoenzymatic Synthesis of Pharmacologically Active Compounds Containing Chiral 1,2-Amino Alcohol Moiety
	4.1 Introduction
		4.1.1 Chirality
		4.1.2 Biocatalysis
			4.1.2.1 Biocatalysis is Green and Sustainable
			4.1.2.2 Industrial Applications of Biocatalysts
		4.1.3 Vicinal Amino Alcohols
	4.2 Synthetic Approaches Toward 1,2-Amino Alcohols
		4.2.1 Chemoenzymatic Synthesis of L-Norephedrine
		4.2.2 Synthesis of Valinol
		4.2.3 Chemoenzymatic Synthesis of Atazanavir
		4.2.4 Chemoenzymatic Synthesis of Levamisole
		4.2.5 Chemoenzymatic Synthesis of Optically Active (R)- and (S)-Aryloxypropanolamines
		4.2.6 Chemoenzymatic Preparation of Trans-(1R,2R)- and Cis (1S,2R)-1-Amino-2-Indanol
		4.2.7 Synthesis of Enantiomerically Pure 2-Aminopentane-1,3-Diol and 2-Amino-1,3,4-Butanetriol (ABT)
		4.2.8 Synthesis of Optically Active Cytoxazone
		4.2.9 Chemoenzymatic and Highly Integrated Synthesis of (S)-Tembamide
		4.2.10 Chemoenzymatic Synthesis of Paclitaxel C₁₃ Side Chain
	4.3 Conclusion
	Acknowledgements
	References
5 1,4-Naphthoquinone: A Privileged Structural Framework in Drug Discovery
	5.1 Introduction
		5.1.1 Overview
	5.2 Various Targets of 1,4-Naphthoquinone for Its Actions
		5.2.1 Bacterial Topoisomerase II-DNA Gyrase for Antibacterial Action
		5.2.2 Mammalian Topoisomerases I and II for Antitumor Action
		5.2.3 HIV-1 Integrase and Proteinase for or Antiviral Action
		5.2.4 Dihydroorotate Dehydrogenase for Antimalarial Action
		5.2.5 Trypanothione and Trypanothione Reductase (TryR) for Leishmanicidal Action
		5.2.6 Mitochondrial Cytochrome (Coenzyme Q) for Antifungal Action
	5.3 Antifungal Activity
	5.4 Antibacterial Activities
	5.5 Anticancer Activity
	5.6 Antileishmanial Activity
	5.7 Antimalarial Activity
	5.8 Antiviral Activity
	5.9 Conclusion
	Acknowledgments
	References
6 Design and Synthesis of Spirobiisoxazoline Derivatives
	6.1 Introduction
	6.2 Literature Review on Spiroisoxazolines
		6.2.1 Chemistry
		6.2.2 Previous Approaches
		6.2.3 Biological Importance
	6.3 Literature Review on Quinones
		6.3.1 Chemistry
		6.3.2 Synthetic Approach
		6.3.3 Biological Importance
	6.4 Review on 1,3 Dipolar Cycloadditions of Oxime Chloride With Allenoates
	6.5 Present Work; Spirobiisoxazoline
		6.5.1 Results and Discussion
			6.5.1.1 Synthetic Studies
			6.5.1.2 Spectral Analysis
		6.5.2 Experimental Section
	6.6 Conclusion
	References
7 Potential of Metal Complexes for the Treatment of Cancer: Current Update and Future Prospective
	7.1 Introduction
	7.2 Conclusion and Future Prospective
	References
8 Design, Synthesis, and Biological Evaluation of Aziridynyl Quinone Derivatives
	8.1 Introduction
	8.2 Aziridines
		8.2.1 Literature Review
		8.2.2 Synthetic Approach
		8.2.3 Biological Importance
	8.3 Quinones
		8.3.1 Literature Review
		8.3.2 Synthetic Approach
		8.3.3 Biological Importance
	8.4 Aziridinyl Quinone Derivatives
		8.4.1 Present Work
		8.4.2 Synthetic Studies
			8.4.2.1 Confirmation of Regioisomers 63 and 63a
			8.4.2.2 Confirmation of Regioselectivity for Diaziridinyl Compounds
		8.4.3 Biological Evaluation
			8.4.3.1 Antibacterial Activity
			8.4.3.2 Minimum Bactericidal Concentration
			8.4.3.3 Biofilm Inhibition Assay
			8.4.3.4 Antifungal Activity
			8.4.3.5 Minimum Fungicidal Concentration
			8.4.3.6 Cytotoxic Activity
		8.4.4 Experimental Section
			8.4.4.1 Chemistry
			8.4.4.2 Biological Studies
	8.5 Conclusion
	References
9 Exploring the Promising Anticancer and Antimicrobial Potential of Bioactive Triazoles and Their Related Compounds
	9.1 Introduction
	9.2 Anticancer Triazole Derivatives
	9.3 Antimicrobial Triazole Derivatives
	9.4 Conclusion
	References
10 Fused Triazolo Isoquinoline Derivatives—Design, Synthesis, and Biological Evaluation
	10.1 Introduction
	10.2 Literature Review on 1,2,4 Triazoles
		10.2.1 Chemistry
		10.2.2 Synthetic Approach
		10.2.3 Biological Importance
	10.3 Review on Isoquinoline and Fused Triazolo Isoquinolines
	10.4 Present Work
	10.5 Results and Discussion
		10.5.1 Synthetic Studies
			10.5.1.1 Confirmation of Regioisomer
		10.5.2 Spectral Analysis
			10.5.2.1 ¹H NMR Spectral and Mass Analysis
			10.5.2.2 ¹³C NMR Spectral Analysis
		10.5.3 Biological Studies
			10.5.3.1 Antifungal Activity
			10.5.3.2 Minimum Fungicidal Concentration
			10.5.3.3 Ergosterol Biosynthesis Inhibition
			10.5.3.4 Cytotoxic Activity
		10.5.4 Molecular Docking Studies
		10.5.5 Experimental Section
			10.5.5.1 Chemistry
			10.5.5.2 Biological Studies
		10.5.6 Molecular Modeling Procedure
	10.6 Conclusion
	References
11 Amide as a Potential Pharmacophore for Drug Designing of Novel Anticonvulsant Compounds
	11.1 Introduction
	11.2 Chemistry of Amides
		11.2.1 Synthesized Methods Utilized for Amide Bond Formation
		11.2.2 Amide Pharmacophore Containing Anticonvulsant Drug
		11.2.3 Anticonvulsant Activity
	11.3 Conclusion
	Acknowledgments
	References
12 Nitric Oxide, Carbon Monoxide, and Hydrogen Sulfide as Biologically Important Signaling Molecules With the Significance of Their Respective Donors in Ophthalmic Diseases
	12.1 Introduction
	12.2 A Meaningful Introduction to Gasotransmitters
	12.3 Biosynthesis and Target of NO, CO, and H₂S
		12.3.1 Biological Synthesis and Target of NO
		12.3.2 Biological Production and Target of CO
		12.3.3 Biosynthesis and Target Sites of H₂S
	12.4 Gasotransmitters in the Mission of Vision (Eye-Health Contribution)
		12.4.1 NO News is Good News for Eyes: NO Donors for the Treatment of Eye Diseases
			12.4.1.1 Nitric Oxide Releasing Molecules (NORMS) and the IOP
		12.4.2 Carbon Monoxide, CORMS, and the Ocular System
		12.4.3 Hydrogen Sulfide and Ophthalmic Diseases
	12.5 Concluding Remarks and Future Outlook
	References
13 Influence of rol Genes for Enhanced Biosynthesis of Potent Natural Products
	13.1 Introduction
	13.2 Secondary Metabolites or Natural Products
		13.2.1 Classes of Natural Products (Secondary Metabolites)
			13.2.1.1 Terpenoids
			13.2.1.2 Phenolic Compounds
			13.2.1.3 Alkaloids
		13.2.2 Strategies to Enhance Natural Products
			13.2.2.1 Plant Cell Culture (Somaclonal Variation)
			13.2.2.2 Genetic Transformation of Plant Cell
			13.2.2.3 Multiple Gene Transfer Through Improving Vectors
		13.2.3 Genetic Engineering/Metabolic Engineering
	13.3 rol Genes
		13.3.1 Origin of rol Genes
		13.3.2 Types of rol Genes
			13.3.2.1 The rolA Gene
			13.3.2.2 The rolB Gene
			13.3.2.3 The rolC Gene
			13.3.2.4 The rolD Gene
		13.3.3 The Combined Effect of Genes rol on Secondary Metabolism
	13.4 Mechanism of Action of rol Genes
		13.4.1 How rol Genes Regulate ROS Production and Mediate Secondary Metabolites Production
			13.4.1.1 Agrobacterium (rol Gene) and ROS
			13.4.1.2 Plants Secondary Metabolism and ROS
			13.4.1.3 Stabilization of Secondary Metabolites Biosynthesis Through rol Genes
	13.5 Impact of rol Gene on Different Secondary Metabolites
		13.5.1 Impact of rol Gene on Alkaliods
		13.5.2 Impact of rol Genes on Flavonoids
		13.5.3 Impact of rol Genes on Terpenoids
	13.6 Conclusion
	References
Index
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