Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents
Abstract
:1. Introduction
2. Results
2.1. Synthesis
2.2. MTT Cytotoxicity Studies
2.3. Interaction with DNA
3. Discussion
4. Materials and Methods
4.1. Chemistry
4.2. General Synthetic Procedures
4.2.1. Synthesis of Analogues of Compound VIII
Synthesis of 7-Acetyl-5,6-Dimethoxy-3-Methylbenzofuran-2-Carboxylic Acid (1)
Synthesis of 7-Acetyl-5,6-Dimethoxy-3-Methylbenzofuran-2-Carboxamide (1a)
Synthesis of Methyl 7-Acetyl-5,6-Dimethoxy-3-Methylbenzofuran-2-Carboxylate (1b)
Synthesis of Methyl 7-Acetyl-3-(Bromomethyl)-5,6-Dimethoxybenzofuran-2-Carboxylate (1c)
Synthesis of 1-(2-Bromo-5,6-Dimethoxy-3-Methylbenzofuran-7-yl)ethanone (1d)
Synthesis of 2-Bromo-1-(2-Bromo-5,6-Dimethoxy-3-Methylbenzofuran-7-yl]ethanone (1e)
4.2.2. Synthesis of Analogues of Compound IX
Synthesis of 6-Acetyl-5-Hydroxy-2-Methylbenzofuran-3-Carboxamide (2a)
Synthesis of 6-Acetyl-4-Bromo-5-Hydroxy-2-Methylbenzofuran-3-Carboxamide (2b)
Synthesis of Methyl 6-Acetyl-5-Hydroxy-2-Methylbenzofuran-3-Carboxylate (2c)
Synthesis of Methyl 6-Acetyl-2-(Bromomethyl)-5-Hydroxybenzofuran-3-Carboxylate (2d)
Synthesis of 6-Acetyl-4-Bromo-5-Hydroxy-2-Methylbenzofuran-3-Carboxylic Acid (2e)
4.2.3. Synthesis of Analogues of Compound X
Synthesis of Methyl 6-Acetyl-5-Methoxy-2-Methylbenzofuran-3-Carboxylate (3) and Methyl 6-(Dibromoacetyl)-5-Methoxy-2-Methyl-1-Benzofuran-3-Carboxylate (X)
Synthesis of Methyl 6-(2,2-Dibromo-1-Hydroxyethyl)-5-Methoxy-2-Methylbenzofuran-3-Carboxylate (3a)
Synthesis of 6-Acetyl-5-Methoxy-2-Methylbenzofuran-3-Carboxylic Acid (3b)
Synthesis of 6-Acetyl-5-Methoxy-2-Methylbenzofuran-3-Carboxamide (3c)
Synthesis of Methyl 6-Acetyl-2-(Bromomethyl)-5-Methoxybenzofuran-3-Carboxylate (3d)
4.3. Anticancer Activity
4.3.1. Cells and Cytotoxicity Assay
4.3.2. Induction of Cell Apoptosis Analyzed by Caspase-3/7 Assay
4.3.3. Digestion of Plasmid DNA with BamHI Restriction Nuclease
5. Conclusions
Author Contributions
Funding
Acknowledgments
Conflicts of Interest
References
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Sample Availability: Not available. |
Compound | clogP |
---|---|
VIII | 2.4327 |
1 | 1.7254 |
1a | 1.3276 |
1b | 2.1533 |
1c | 2.4745 |
1d | 3.0089 |
1e | 3.3301 |
IX | 3.5663 |
2a | 1.1219 |
2b | 1.8471 |
2d | 2.2688 |
2e | 2.2449 |
X | 3.1168 |
3a | 2.9350 |
3b | 1.7954 |
3c | 1.3972 |
3d | 2.5445 |
Compound | HeLa | K562 | MOLT-4 | HUVEC |
---|---|---|---|---|
1c | 50 | 25 | 180 | 30 |
1e | 28 | 41 | 70 | 30 |
2d | 35 | 20 | 35 | 30 |
3a | 80 | 85 | 85 | 67 |
3d | 35 | 28 | 55 | 6 |
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Napiórkowska, M.; Cieślak, M.; Kaźmierczak-Barańska, J.; Królewska-Golińska, K.; Nawrot, B. Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents. Molecules 2019, 24, 1529. https://doi.org/10.3390/molecules24081529
Napiórkowska M, Cieślak M, Kaźmierczak-Barańska J, Królewska-Golińska K, Nawrot B. Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents. Molecules. 2019; 24(8):1529. https://doi.org/10.3390/molecules24081529
Chicago/Turabian StyleNapiórkowska, Mariola, Marcin Cieślak, Julia Kaźmierczak-Barańska, Karolina Królewska-Golińska, and Barbara Nawrot. 2019. "Synthesis of New Derivatives of Benzofuran as Potential Anticancer Agents" Molecules 24, no. 8: 1529. https://doi.org/10.3390/molecules24081529