The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure-Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles
Abstract
:1. Introduction
2. Results and Discussion
2.1. Synthesis and Characterization
2.2. Cytotoxicity Properties
2.3. Structure-Activity Relationship (SAR)
3. Materials and Methods
3.1. Materials
3.2. Instrumentation
3.3. Synthesis
3.3.1. General procedure for the Synthesis 6-(2,5-dichlorothiophen-3-yl)-2-methoxy-4-(4-methoxyphenyl)pyridines (5a–i) and (6a–g)
3.3.2. Characterization Data for Products
3.4. Cell Culture and Maintenance
3.5. Cytotoxicity Assay
4. Conclusions
Supplementary Materials
Author Contributions
Funding
Conflicts of Interest
References
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Sample Availability: Samples of the compounds 5a–i are available from the authors. |
Tested cpd. | IC50 Values (µM) | ||||||
---|---|---|---|---|---|---|---|
DU145 | SI | HepG2 | SI | MDA-MB-231 | SI | HSF1184 | |
5a | >100 | ND | 49.55 ± 0.51 | 1.66 | 21.15 ± 0.37 | 3.90 | 82.39 ± 0.04 |
5b | >100 | ND | 9.48 ± 0.63 | 12.08 | >100 | ND | 114.54 ± 0.38 |
5c | 42.36 ± 0.21 | 2.18 | >100 | ND | 28.34 ± 0.42 | 3.26 | 92.38 ± 0.38 |
5d | 3.63 ± 0.17 | 116.65 | 1.62 ± 0.15 | 261.39 | 2.59 ± 0.04 | 163.49 | 423.45 ± 0.49 |
5f | 27.45 ± 0.63 | 3.48 | 18.34 ± 0.31 | 5.21 | 43.49 ± 0.06 | 2.20 | 95.49 ± 0.29 |
5g | 4.97 ± 0.35 | 27.28 | 2.11 ± 0.26 | 64.26 | 1.93 ± 0.03 | 70.25 | 135.59 ± 0.55 |
5h | 1.77 ± 0.38 | 105.93 | 1.53 ± 0.38 | 122.54 | 2.14 ± 0.06 | 87.61 | 187.49 ± 0.14 |
5i | 1.82 ± 0.21 | 128.82 | 1.72 ± 0.42 | 136.31 | 1.38 ± 0.03 | 169.89 | 234.45 ± 0.27 |
6a | 53.49 ± 0.02 | 1.67 | 32.31 ± 0.23 | 2.77 | 15.34 ± 0.41 | 5.82 | 89.34 ± 0.55 |
6b | 64.59 ± 0.08 | 1.59 | 39.49 ± 0.58 | 2.59 | 52.39 ± 0.31 | 1.95 | 102.39 ± 0.30 |
6c | 21.65 ± 0.12 | 5.19 | 11.28 ± 0.22 | 9.96 | 10.34 ± 0. 37 | 10.87 | 112.38 ± 0.47 |
6d | 29.45 ± 0.88 | 3.14 | 64.59 ± 0.33 | 1.43 | 15.43 ± 0.48 | 6.00 | 92.55 ± 0.42 |
6f | 18.45 ± 0.02 | 5.68 | 38.45 ± 0.62 | 2.73 | 64.39 ± 0.28 | 1.63 | 104.83 ± 0.71 |
6g | 25.42 ± 0.38 | 3.33 | 39.43 ± 0.09 | 2.14 | 18.34 ± 0.34 | 4.61 | 84.56 ± 0.40 |
5-fluorouracil | 1.92 ± 0.24 | 96.60 | 1.65 ± 0.09 | 112.41 | 2.21 ± 0.28 | 83.93 | 185.48 ± 0.48 |
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Al-Refai, M.; Ibrahim, M.M.; Nurul Azmi, M.; Osman, H.; Abu Bakar, M.H.; Geyer, A. The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure-Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles. Molecules 2019, 24, 4072. https://doi.org/10.3390/molecules24224072
Al-Refai M, Ibrahim MM, Nurul Azmi M, Osman H, Abu Bakar MH, Geyer A. The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure-Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles. Molecules. 2019; 24(22):4072. https://doi.org/10.3390/molecules24224072
Chicago/Turabian StyleAl-Refai, Mahmoud, Mohammad M. Ibrahim, Mohamad Nurul Azmi, Hasnah Osman, Mohamad Hafizi Abu Bakar, and Armin Geyer. 2019. "The Synthesis, Characterization, Cytotoxic Activity Assessment and Structure-Activity Relationship of 4-Aryl-6-(2,5-dichlorothiophen-3-yl)-2-methoxypyridine-3-carbonitriles" Molecules 24, no. 22: 4072. https://doi.org/10.3390/molecules24224072