Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity
Abstract
:1. Introduction
2. Materials and Methods
2.1. Chemistry
2.1.1. Synthesis of the Starting Materials (2)
2.1.2. Synthesis of 2-Oxo-1,2-dihydroquinoline-3-carboxylic acid (4)
2.1.3. General Procedures for the Preparation of Ethyl 3-aryl-2-cyanoccrylamates (6a–d)
2.1.4. General Procedures for Synthesis of 1-[2-Cyano-2-(ethoxy) carbonyl-1-arylvinyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (7a–d)
2.1.5. General Procedures for Preparation of 1-[(Aryl)(3-amino-5-oxopyrazolidine-4-ylidene)methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic acid (8a–d)
2.2. Biological Assay
2.2.1. In vitro Anticancer Effect of the Compounds 7a–d and 8a–d Against MCF-7 Cell Line
2.2.2. Cell-Cycle Analysis
2.3. Statistical Analysis
3. Results and Discussion
3.1. Chemistry
3.2. In Vitro Cytotoxic Activity Against MCF-7 Cell Line
3.3. Cell-Cycle Analysis
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Acknowledgments
Conflicts of Interest
References
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Compound | IC50 Values (μM)/MCF-7 |
---|---|
7a | >50 |
7b | 3.87 ± 0.33 c |
7c | 1.73 ± 0.27 a |
7d | >50 |
8a | 17.32 ± 0.44 e |
8b | 5.67 ± 0.21 d |
8c | 4.03 ± 0.60 c |
8d | >50 |
Dox | 2.82 ± 0.07 b |
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Gaber, A.; Alsanie, W.F.; Alhomrani, M.; Alamri, A.S.; El-Deen, I.M.; Refat, M.S. Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity. Crystals 2021, 11, 571. https://doi.org/10.3390/cryst11050571
Gaber A, Alsanie WF, Alhomrani M, Alamri AS, El-Deen IM, Refat MS. Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity. Crystals. 2021; 11(5):571. https://doi.org/10.3390/cryst11050571
Chicago/Turabian StyleGaber, Ahmed, Walaa F. Alsanie, Majid Alhomrani, Abdulhakeem S. Alamri, Ibrahim M. El-Deen, and Moamen S. Refat. 2021. "Synthesis of 1-[(Aryl)(3-amino-5-oxopyrazolidin-4-ylidene) methyl]-2-oxo-1,2-dihydroquinoline-3-carboxylic Acid Derivatives and Their Breast Anticancer Activity" Crystals 11, no. 5: 571. https://doi.org/10.3390/cryst11050571