Chemistry of Biologically Potent Natural Products and Synthetic Compounds

432 Pages·2021·14.051 MB·English

by  Shahid Ul-Islam, Javid Ahmad Banday

Chemistry of Biologically
Potent Natural Products and
Synthetic Compounds
Scrivener Publishing
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Emerging Trends in Medicinal and Pharmaceutical Chemistry
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erging Trends in Medicinal Chemistry and Pharmacology Series is intendedto provide recenttrends,
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Chemistry of Biologically
Potent Natural Products and
Synthetic Compounds
Edited by
Shahid-ul-Islam
and
Javid Ahmad Banday
This edition first published 2021 by John Wiley & Sons, Inc., 111 River Street, Hoboken, NJ 07030, USA
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Library of Congress Cataloging-in-Publication Data
ISBN 978-1-119-64034-9
Cover image: Pixabay.Com
Cover design by Russell Richardson
Set in size of 11pt and Minion Pro by Manila Typesetting Company, Makati, Philippines
Printed in the USA
10 9 8 7 6 5 4 3 2 1
Contents
Preface xiii
1 Medicinal Importance of Plant Metabolites 1
Sunita Panchawat and Chetna Ameta
1.1 Introductory Note 1
1.2 Primary and Secondary Metabolites 3
1.3 Functional Roles of Secondary Metabolites 3
1.4 Source and Production of Secondary Metabolites 4
1.5 Classification of Secondary Metabolic Substances 7
1.5.1 Terpenes 8
1.5.2 Phenol-Based Compounds 9
1.5.3 Nitrogen-Containing Secondary Metabolites 10
1.5.3.1 Alkaloids 10
1.5.4 Secondary Metabolites Having Sulfur 11
1.6 Bioactivity of Secondary Metabolites 12
1.6.1 As Antioxidants 12
1.6.2 As Antimicrobials 13
1.6.3 As Anti-Diabetics Agents 13
1.7 Conclusion and Future Perspectives 14
References 14
2 Advances in Natural Products-Based Antiviral Agents 21
Zhipeng Fu, Luis Menéndez-Arias, Xinyong Liu
and Peng Zhan
2.1 Introduction 21
2.2 Anti-HIV Agents 22
2.2.1 Terpenes 23
2.2.2 Phenylpropanoids 24
2.2.3 Anthraquinones 25
2.2.4 Alkaloids 26
2.3 Natural Alkaloids With Activity Against HBV
and HCV Infections 26
v
vi Contents
2.4 Anti-Influenza Virus Agents 28
2.5 Natural Products Active Against Herpesviruses 30
2.6 Natural Products Against Chikungunya Virus 31
2.7 Natural Products Targeting Dengue Virus 32
2.8 Natural Products Targeting Coronaviruses 33
2.9 Natural Products Against Other Viral Infections 36
2.10 Conclusion 37
Acknowledgements 37
References 37
3 Bioactive Component of Black Pepper-Piperine:
Structure-Activity Relationship and Its Broad-Spectrum
Activity—An Overview 43
Arthi Sivashanmugam and Sivan Velmathi
List of Abbreviations 44
3.1 Introduction: What is a Natural Product? 44
3.2 Black Pepper 48
3.2.1 Constituents of Black Pepper 51
3.2.2 Major Alkaloids of Black Pepper 51
3.3 Piperine—Active Molecule of Pepper 52
3.3.1 Isolation of Piperine 52
3.3.2 Piperine as Potential Drug 54
3.3.2.1 Metabolism of Piperine 54
3.3.2.2 Structure-Activity Relationship 55
3.3.2.3 Piperine and Piperine Analogs 59
3.3.2.4 Synergistic Activity of Piperine 72
3.4 Overall Summary and Conclusion 88
References 89
4 Chemoenzymatic Synthesis of Pharmacologically Active
Compounds Containing Chiral 1,2-Amino Alcohol Moiety 93
Pankaj Gupta and Neha Mahajan
4.1 Introduction 94
4.1.1 Chirality 94
4.1.2 Biocatalysis 96
4.1.2.1 Biocatalysis is Green and Sustainable 97
4.1.2.2 Industrial Applications of Biocatalysts 98
4.1.3 Vicinal Amino Alcohols 99
4.2 Synthetic Approaches Toward 1,2-Amino Alcohols 102
4.2.1 Chemoenzymatic Synthesis of L-Norephedrine 102
Contents vii
4.2.2 Synthesis of Valinol 106
4.2.3 Chemoenzymatic Synthesis of Atazanavir 107
4.2.4 Chemoenzymatic Synthesis of Levamisole 107
4.2.5 Chemoenzymatic Synthesis of Optically Active
(R)- and (S)-Aryloxypropanolamines 108
4.2.6 Chemoenzymatic Preparation of Trans-(1R,2R)-
and Cis (1S,2R)-1-Amino-2-Indanol 112
4.2.7 Synthesis of Enantiomerically Pure 2-Aminopentane-
1,3-Diol and 2-Amino-1,3,4-Butanetriol (ABT) 113
4.2.8 Synthesis of Optically Active Cytoxazone 115
4.2.9 Chemoenzymatic and Highly Integrated Synthesis
of (S)-Tembamide 116
4.2.10 Chemoenzymatic Synthesis of Paclitaxel C
13
Side Chain 117
4.3 Conclusion 118
Acknowledgements 119
References 119
5 1,4-Naphthoquinone: A Privileged Structural Framework
in Drug Discovery 133
Umar Ali Dar, Mehnaz Kamal and Shakeel A. Shah
5.1 Introduction 133
5.1.1 Overview 134
5.2 Various Targets of 1,4-Naphthoquinone for Its Actions 135
5.2.1 Bacterial Topoisomerase II-DNA Gyrase
for Antibacterial Action 135
5.2.2 Mammalian Topoisomerases I and II
for Antitumor Action  135
5.2.3 HIV-1 Integrase and Proteinase for or Antiviral
Action 135
5.2.4 Dihydroorotate Dehydrogenase for Antimalarial
Action 136
5.2.5 Trypanothione and Trypanothione Reductase
(TryR) for Leishmanicidal Action 137
5.2.6 Mitochondrial Cytochrome (Coenzyme Q)
for Antifungal Action 137
5.3 Antifungal Activity 137
5.4 Antibacterial Activities 140
5.5 Anticancer Activity 142
viii Contents
5.6 Antileishmanial Activity 145
5.7 Antimalarial Activity 147
5.8 Antiviral Activity 149
5.9 Conclusion 149
Acknowledgments 150
References 150
6 Design and Synthesis of Spirobiisoxazoline Derivatives 155
K. Jones Madhuswapnaja, Satyanarayana Yennam
and Murthy Chavali
6.1 Introduction 155
6.2 Literature Review on Spiroisoxazolines 157
6.2.1 Chemistry 157
6.2.2 Previous Approaches 159
6.2.3 Biological Importance 163
6.3 Literature Review on Quinones 166
6.3.1 Chemistry 166
6.3.2 Synthetic Approach 167
6.3.3 Biological Importance 169
6.4 Review on 1,3 Dipolar Cycloadditions of Oxime Chloride
With Allenoates 171
6.5 Present Work; Spirobiisoxazoline 172
6.5.1 Results and Discussion 172
6.5.1.1 Synthetic Studies 172
6.5.1.2 Spectral Analysis 176
6.5.2 Experimental Section 178
6.6 Conclusion 179
References 179
7 Potential of Metal Complexes for the Treatment of Cancer:
Current Update and Future Prospective 183
Shipra Yadav
7.1 Introduction 184
7.2 Conclusion and Future Prospective 195
References 196
8 Design, Synthesis, and Biological Evaluation of Aziridynyl
Quinone Derivatives 205
K. Jones Madhuswapnaja, Satyanarayana Yennam
and Murthy Chavali
8.1 Introduction 206
8.2 Aziridines 207