Arylcyanomethylenequinone Oximes: An Overview of Synthesis, Chemical Transformations, and Biological Activity
Abstract
:1. Introduction
2. Synthesis of Arylcyanomethylenequinone Oximes and Some of Their Derivatives
2.1. The Condensation of (Hetero) Arylacetonitriles with Nitro (Hetero) Arenes
2.2. The Conversion of Quinone Methide Derivatives Using Hydroxylamine
3. Chemical Transformation of Arylcyanomethylenequinone Oximes
3.1. The Oxime–Nitroso Tautomerism Equilibrium in Arylcyanomethylenequinone Oxime
3.2. The Reduction Reactions of Arylcyanomethylenequinone Oxime
3.3. The Oxidation Reactions of Arylcyanomethylenequinone Oxime
3.4. The Substitution of a Hydrogen Atom at the Oxime Group in Arylcyanomethylenequinone Oxime
3.4.1. The Acylation of a Hydrogen Atom at the Oxime Group
3.4.2. The Alkylation of a Hydrogen Atom at the Oxime Group
3.4.3. Other Substitution Reactions at Oxygen Atom of the Oxime Group
4. Biological Properties of Arylcyanomethylenequinone Oximes
4.1. Antiallergic Activity
4.2. Antifungal Activity
4.3. Anti-Inflammatory Activity
4.4. Anticancer Activity
4.5. Positive Inotropic and Lusitropic Effects
4.6. Potential Application of Arylcyanomethylenequinone Oximes in Veterinary Medicine
4.7. Potential Application of Arylcyanomethylenequinone Oximes as Plant Protection Products
5. Conclusions and Future Outlook
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
Sample Availability
References
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Product (Yield [%]) | R | R1 | R2 | R3 | Product (Yield [%]) | R | R1 | R2 | R3 | ||
---|---|---|---|---|---|---|---|---|---|---|---|
12aa | (53) | -H | -H | -H | -Cl | 12be | (94) | -Cl | -Cl | -H | -Cl |
12ab | (25) | -H | -H | -H | -OCH3 | 12bf | (92) | -Cl | -Cl | -Cl | -H |
12ac | (76) | -H | -H | -H | -CH3 | 12bg | (77) | -Cl | -Cl | -H | -CH3 |
12ad | (92) | -H | -Cl | -H | -H | 12bh | (80) | -Cl | -OCH3 | -H | -H |
12ae | (93) | -H | -Cl | -H | -Cl | 12bi | (81) | -Cl | -OCH3 | -H | -Cl |
12af | (53) | -H | -Cl | -Cl | -H | 12bj | (80) | -Cl | -OCH3 | -H | -OCH3 |
12ag | (77) | -H | -Cl | -H | -CH3 | 12bk | (60) | -Cl | -CH3 | -H | -H |
12ah | (87) | -H | -OCH3 | -H | -H | 12bm | (80) | -Cl | -CH3 | -Cl | -H |
12ai | (82) | -H | -OCH3 | -H | -Cl | 12bn | (43) | -Cl | -CH3 | -H | -CH3 |
12aj | (88) | -H | -OCH3 | -H | -OCH3 | 12ce | (91) | -OCH3 | -Cl | -H | -Cl |
12ak | (72) | -H | -CH3 | -H | -H | 12cg | (80) | -OCH3 | -Cl | -H | -CH3 |
12al | (92) | -H | -CH3 | -H | -Cl | 12cf | (65) | -OCH3 | -Cl | -Cl | -H |
12am | (82) | -H | -CH3 | -Cl | -H | 12ci | (84) | -OCH3 | -OCH3 | -H | -Cl |
12an | (53) | -H | -CH3 | -H | -CH3 | 12cj | (65) | -OCH3 | -OCH3 | -H | -OCH3 |
12ba | (100) | -Cl | -H | -H | -Cl | 12cl | (88) | -OCH3 | -CH3 | -H | -Cl |
12bb | (89) | -Cl | -H | -H | -OCH3 | 12cm | (80) | -OCH3 | -CH3 | -Cl | -H |
12bd | (100) | -Cl | -Cl | -H | -H | 12cn | (69) | -OCH3 | -CH3 | -H | -CH3 |
Product (Yield (%)) | R | R1 | Product (Yield (%)) | R | R1 | ||
---|---|---|---|---|---|---|---|
33aa | (67) | -H | -CH3 | 33ca | (65) | -OCH3 | -CH3 |
33ab | (69) | -H | -C2H5 | 33cb | (70) | -OCH3 | -C2H5 |
33ba | (86) | -Cl | -CH3 | 33da | (90) | -CH3 | -CH3 |
33bb | (76) | -Cl | -C2H5 | 33db | (92) | -CH3 | -C2H5 |
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Kula, K.; Nagatsky, R.; Sadowski, M.; Siumka, Y.; Demchuk, O.M. Arylcyanomethylenequinone Oximes: An Overview of Synthesis, Chemical Transformations, and Biological Activity. Molecules 2023, 28, 5229. https://doi.org/10.3390/molecules28135229
Kula K, Nagatsky R, Sadowski M, Siumka Y, Demchuk OM. Arylcyanomethylenequinone Oximes: An Overview of Synthesis, Chemical Transformations, and Biological Activity. Molecules. 2023; 28(13):5229. https://doi.org/10.3390/molecules28135229
Chicago/Turabian StyleKula, Karolina, Roman Nagatsky, Mikołaj Sadowski, Yevheniia Siumka, and Oleg M. Demchuk. 2023. "Arylcyanomethylenequinone Oximes: An Overview of Synthesis, Chemical Transformations, and Biological Activity" Molecules 28, no. 13: 5229. https://doi.org/10.3390/molecules28135229