Spirooxindole

Chemistry, Synthesis, Characterization and Biological Significance

1st Edition - June 12, 2024
Editors: Gautam Patel, Vraj R. Shah, Tuan Anh Nguyen, Kalim Deshmukh
Language: English
Paperback ISBN:
9 7 8 - 0 - 4 4 3 - 2 2 3 2 4 - 2
eBook ISBN:
9 7 8 - 0 - 4 4 3 - 2 2 3 2 5 - 9

Spirooxindole: Chemistry, Synthesis, Characterization and Biological Significance examines the current state-of-the-art, recent progress, and new challenges associated with the… Read more

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Spirooxindole: Chemistry, Synthesis, Characterization and Biological Significance examines the current state-of-the-art, recent progress, and new challenges associated with the development of spirooxindole derivatives for various medicinal applications. Owing to their exceptional properties, these compounds can be used in various fields, including chemical and pharma industries, and in clinical research. This book has chapters written by experts in several different areas. It serves as a useful reference book for scientists, industrial practitioners, graduate students, and other professionals in the field of hetrocyclic chemistry, medicinal chemistry, organic synthesis clinical research and chemical sciences.

The growing interest among the academics and industrial researchers in the field of organic chemistry and medicinal chemistry is the driving force for the presentation of this edited book.

Cover image
Title page
Table of Contents
Copyright
List of contributors
About the editors
Preface
Chapter 1. Synthesis of spirooxindoles by [3+2] cycloadditions
Abstract
1.1 Introduction
1.2 Cycloadditions of isatin-based dipolarophiles
1.3 [3+2] Cycloadditions of isatin-derived 1,3-dipoles
1.4 Cycloadditions of isatin-derived 1,3-dipoles and dipolarophiles for dispirooxindoles
1.5 Intramolecular [3+2] cycloadditions
1.6 Summary
References
Chapter 2. Synthesis of spirooxindoles under ultrasonication
Abstract
2.1 Introduction
2.2 Construction of three member ring on C-3 carbon of oxindole
2.3 Construction of five member ring on C-3 carbon oxindole
2.4 Construction of six member ring on C-3 carbon of oxindoles
2.5 Construction of seven member ring on C-3 carbon
2.6 Conclusion
References
Chapter 3. Organocatalyzed cycloaddition of N-2,2,2-trifluoroethylisatin ketimines for synthesis of CF3-containing spirooxindoles
Abstract
3.1 Introduction
3.2 Organocatalyzed asymmetric [3+2] cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines
3.3 Organocatalyzed asymmetric [4+3] cycloaddition reaction of N-2,2,2-trifluoroethylisatin ketimines
3.4 Conclusions
References
Chapter 4. Regio- and stereoselective synthesis of spirooxindole scaffold
Abstract
4.1 Introduction
4.2 Regio- and stereoselective synthesis of spirooxindole scaffolds
4.3 Conclusion
References
Chapter 5. Synthesis of spiroheterocyclic compounds by using isatin
Abstract
5.1 Introduction
5.2 Use of isatin for synthesis of spiroheterocyclic compounds
Acknowledgments
References
Chapter 6. Synthesis of highly functionalized spirooxindole derivatives via multicomponent [3+2] cycloaddition reactions
Abstract
6.1 Introduction
6.2 Synthesis of highly functionalized 3,2′-spirooxindoles via multicomponent 1,3-dipolar cycloaddition reaction
6.3 Spirooxindole synthesis through ylideneoxindole multicomponent reactions
References
Chapter 7. Organocatalyzed enantioselective synthesis of spirooxindole scaffolds
Abstract
7.1 Introduction
7.2 Multicomponent reactions
7.3 Two-component reactions
7.4 One-component reactions
7.5 Other synthetic precursors
7.6 Challenges and future perspectives
References
Chapter 8. Synthesis of spirooxindoles and its derivatives using green and nanotechnology
Abstract
8.1 Introduction
8.2 Synthesis of spirooxindole and its derivatives
8.3 Synthesis of spirooxindole and its derivatives using organocatalysts
8.4 Conclusion
References
Chapter 9. Recent strategies in the synthesis of spirooxindole scaffolds (stereoselective synthesis)
Abstract
9.1 Introduction
9.2 Stereoselective synthesis of spirooxindoles
9.3 Conclusion
Acknowledgments
Conflict of Interest
References
Chapter 10. Characterization techniques for synthesized spirooxindole scaffold
Abstract
10.1 Introduction
10.2 Characterization techniques
10.3 Future perspectives
10.4 Conclusion
References
Chapter 11. Stereoselective synthesis of spirooxindole scaffold
Abstract
11.1 Introduction
11.2 Summary and conclusions
Acknowledgments
Abbreviation
References
Chapter 12. Synthesis of hybrid spirooxindoles
Abstract
12.1 Introduction
12.2 Summary and conclusions
Acknowledgments
Abbreviation
References
Chapter 13. Anticancer properties of spirooxindole derivatives
Abstract
13.1 Introduction
13.2 Synthesis and biological evaluation of spirooxindole fused/hybrid with other heterocycles as anticancer agents
13.3 Conclusion
Funding information
Conflict of interest
Abbreviations
References
Chapter 14. Medicinal application of spirooxindole and its derivatives: an introduction
Abstract
14.1 Introduction
14.2 Biological characteristics of spirooxindole based natural products
14.3 Anticancer activity
14.4 Antimicrobial/bacterial/fungal activities
14.5 Antiinflammatory activity
14.6 Spirooxindole based derivatives as cholinesterase inhibitors
14.7 Analgesic activity
14.8 Antioxidant activity
14.9 Antileishmanial and antiplasmodial activities
14.10 Antiviral activity
14.11 Antiatherosclerotic activity
14.12 Antidiabetic activity
14.13 Conclusion
References
Chapter 15. Spirooxindole derivatives as an anticancer agents: Synthetic developments, structure–activity relationship, and biological applications
Abstract
15.1 Introduction
15.2 Spirooxindole
15.3 Synthetic schemes of spirooxindole derivatives as an anticancer agent
15.4 Conclusion
Declaration of author's contribution
Ethical approval
Acknowledgment
Competing interest
Abbreviations
References
Chapter 16. Spirooxindole derivatives as an anticancer agent
Abstract
16.1 Background
16.2 Bioactive natural spirooxindoles
16.3 Synthetic spirooxindole advances to clinical trials as promising anticancer agents
16.4 Representative examples of anticancer spirooxindole analogs
16.5 Conclusion
16.6 Dedication
References
Chapter 17. Spirooxindole derivatives as kinase-based anticancer agents
Abstract
17.1 Introduction
17.2 Natural products containing spirooxindoles as kinase-based anticancer agents
17.3 C3-substituted five-membered spirooxindoles as kinase-based anticancer agents
17.4 C3-substituted-six-membered spirooxindoles as kinase-based anticancer agents
17.5 The journey of CFI-40095, a case study
17.6 Conclusion
References
Chapter 18. Spirooxindole derivatives as antioxidant agents
Abstract
18.1 Introduction
18.2 Experimental methods for evaluating antioxidant activity
18.3 Studies on the antioxidant properties of spirooxindoles
18.4 Application of antioxidants
18.5 Future perspectives
18.6 Conclusion
References
Chapter 19. Spirooxindole derivatives as promising antiviral agents: Structure–activity relationship studies and biological perspectives
Abstract
19.1 Introduction
19.2 Spirooxindole derivatives as antirespiratory syncytial virus agent
19.3 Spirooxindole derivatives as antihuman immunodeficiency virus agent
19.4 Spirooxindole derivatives as antiinfluenza agent
19.5 Spirooxindole derivatives as antidengue agent
19.6 Other spirooxindole containing antiviral agents
19.7 Conclusions and future perspectives
Declaration of author's contribution
Ethical approval
Acknowledgment
Competing interest
Abbreviations
References
Further reading
Chapter 20. Spirooxindole derivatives as an agrochemical
Abstract
20.1 Introduction
20.2 Molecular design
20.3 Synthetic method
20.4 Antiviral activities
20.5 Fungicidal activities
20.6 Insecticidal activities
20.7 Conclusion
References
Chapter 21. Other medicinal applications
Abstract
21.1 Introduction
21.2 Antidiabetic potential
21.3 Cholinesterase inhibitors
21.4 Anthelmintic activities
21.5 Anticonvulsant activity
21.6 Antiprotozoal activity
21.7 Antimalarial activity
21.8 Bovine serum albumin binding
21.9 Zebrafish embryo toxicity
21.10 Antiatherosclerotic agents (sterol O-acyltransferase inhibitors)
21.11 Sirtuin 2 inhibition
21.12 hNaV1.7 (human voltage-gated sodium channel subtype 1.7) inhibitors
21.13 Sensing applications
21.14 DNA cleavage
21.15 DNA interaction
21.16 Mineralocorticoid receptor antagonists
21.17 Antiobesity agents
21.18 Cognitive disorders
21.19 Antifungal and anticoagulant
21.20 Cardioprotectant effects
21.21 Conclusion
References
Chapter 22. Spirooxindole derivatives as antibacterial agents
Abstract
22.1 Introduction
22.2 Glimpse of the in vitro antibacterial susceptibility testing methods
22.3 Spirooxindoles as antibacterial agents
22.4 Conclusion
References
Chapter 23. Medicinal applications of spirooxindole and its derivatives
Abstract
23.1 An overview of spirooxindoles
23.2 Introduction
23.3 Pharmacological significance of spirooxindoles
23.4 Common synthetic root for accessing spiroheterocyclic compounds
23.5 Case studies and recent advancements of spirooxindole and its derivatives
23.6 Challenges and future perspectives
23.7 Conclusion
References
Chapter 24. Anticancer effect of spirooxindole derivatives
Abstract
24.1 Introduction
24.2 Naturally occurring spirooxindoles as anticancer agent
24.3 Synthetic spirooxindoles as anticancer agent
24.4 Conclusion
References
Chapter 25. Anticancer potential of spirooxindole derivatives
Abstract
25.1 Introduction
25.2 Literature survey on the C-3 spirooxindole derivatives
25.3 Synthesis of spirooxindoles via different routes
25.4 Microwave-irradiation assessment for the formation of spirooxindole derivatives
25.5 Conclusion
References
Index

Gautam Patel

Gautam Patel obtained PG from Institute of Science and Technology for Advanced Studies and Research (ISTAR), Vallabh Vidya Nagar and Doctoral degree from the M. S. University of Baroda, India. He is the Head and an Associate Professor at the Chemistry Department, Parul Institute of Applied Science, Parul University, India. His area of specialization is organic synthesis, green chemistry, nanosciences and nanotechnology. He has 3 patents to his name.

Affiliations and expertise

Head and Associate Professor, Parul University, India

Vraj R. Shah

Vraj R. Shah has received his B.Sc. in Industrial Chemistry from ITM Vocational University and M.Sc. degrees in Industrial Chemistry from ITM (SLS) Baroda University, Vadodara. Following his graduation, he is currently working as a graduate research assistant at the department of Chemical and Biological Engineering at The University of Alabama, USA. He has published 5 research papers in the peer-review international journals. He has contributed 8 book chapters with peer reviewed books of international publishers. His research interest mainly focuses on organic synthesis, medicinal chemistry, computational simulations, membrane synthesis, and nanotechnology. In addition, he has also received the prestigious GCF fellowship from University of Alabama to pursue his doctoral degree. Moreover, he has also been awarded “Best young researcher presentation ” from Sardar Vallabhbhai Patel National Institute of Technology (SVNIT).

Affiliations and expertise

Department of Applied Chemistry, School of Science, ITM (SLS) Baroda University, India

Tuan Anh Nguyen

Tuan Anh Nguyen is Principal Research Scientist at the Institute for Tropical Technology, Vietnam Academy of Science and Technology, Hanoi, Vietnam. His research focuses on advanced nanomaterials and nanotechnology for corrosion and materials integrity in transportation systems. His research activities include smart coatings, conducting polymers, corrosion and protection of metals/concrete, antibacterial materials, and advanced nanomaterials.

Affiliations and expertise

Senior Principal Research Scientist, Institute for Tropical Technology, Vietnam Academy of Science and Technology, Hanoi, Vietnam

Kalim Deshmukh

Kalim Deshmukh is a Senior Researcher at the New Technologies-Research Centre, University of West Bohemia, Pilsen, Czech Republic. His research interest is mainly focused on the synthesis, characterization, and property investigations of polymer nanocomposites reinforced with different nanofillers (including various nanoparticles and carbon allotropes such as carbon black, carbon nanotubes, and graphene) and their derivatives for energy storage, energy harvesting, gas sensing, EMI shielding, and high-k dielectric applications.

Affiliations and expertise

Senior Researcher, New Technologies - Research Centre, University of West Bohemia, Czech Republic