Synthesis, Characterization, Docking Study and Biological Activates of New 3-Aminorhodanine Derivatives
DOI:
https://doi.org/10.32947/ajps.v24i3.1072Keywords:
EGFR mutantation, Lung Cancer, 3- aminorhodanineAbstract
Abstract: Increase in fatalities among cancer patients is one of untreated facts and today cancer remains one of the main health issues. The most common cause of cancer death is lung cancer. Rhodanine has been recognized as a privileged scaffold in medicinal chemistry due to its well-known ability to demonstrate a broad range of biological activities,
and most of its derivatives exhibited remarkable anticancer activity in the (μg/mL) concentration range, while causing negligible cytotoxicity to normal cells. New N- and 5- disubstituted aminorhodanine derivatives were synthesized by Schiff base and Knoevenagel condensation reactions over two consecutive steps. Human cancer cells and Hdfn (human dermal fibroblasts isolated from neonatal foreskin) cells line, were used to evaluate the synthesized compounds’ activity by MTT assay. The new compounds revealed higher anticancer activity against A549 lung cells cancer when compared with reference drug Erlotinib (anticancer drug) and determined no toxicity or safety on normal cell. Among the tested compounds, 2b2 compound show potent anticancer activity which have IC50 about (55.8 μg/mL).
References
- C. Fitzmaurice et al., “The global burden of cancer 2013,” JAMA Oncol., vol. 1, no. 4, pp. 505–527, 2015.
- K. Mc Namara, H. Alzubaidi, and J. K. Jackson, “Cardiovascular disease as a leading cause of death: how are pharmacists getting involved?,” Integr. Pharm. Res. Pract., pp. 1–11, 2019. DOI: https://doi.org/10.2147/IPRP.S133088
- V. T. DeVita, T. S. Lawrence, and S. A. Rosenberg, Cancer of the skin: cancer: principles & practice of oncology. Lippincott Williams & Wilkins, 2015.
- E. A. Semenova, R. Nagel, and A. Berns, “Origins, genetic landscape, and emerging therapies of small cell lung cancer,” Genes Dev., vol. 29, no. 14, pp. 1447–1462, 2015. DOI: https://doi.org/10.1101/gad.263145.115
- Y. Ai et al., “Residual multilayer perceptrons for genotype-guided recurrence prediction of non-small cell lung cancer,” in 2022 44th Annual International Conference of the IEEE Engineering in Medicine & Biology Society (EMBC), 2022, pp. 447–450. DOI: https://doi.org/10.1109/EMBC48229.2022.9871896
- T. Wang, R. A. Nelson, A. Bogardus, and F. W. Grannis Jr, “Five‐year lung cancer survival: which advanced stage nonsmall cell lung cancer patients attain long‐term survival?,” Cancer Interdiscip. Int. J. Am. Cancer Soc., vol. 116, no. 6, pp. 1518–1525, 2010. DOI: https://doi.org/10.1002/cncr.24871
- C. Xue et al., “National survey of the medical treatment status for non-small cell lung cancer (NSCLC) in China,” Lung Cancer, vol. 77, no. 2, pp. 371–375, 2012. DOI: https://doi.org/10.1016/j.lungcan.2012.04.014
- K. D. Miller et al., “Cancer treatment and survivorship statistics, 2016,” CA. Cancer J. Clin., vol. 66, no. 4, pp. 271–289, 2016. DOI: https://doi.org/10.3322/caac.21349
- N. M. Aljamali and I. O. Alfatlawi, “Synthesis of sulfur heterocyclic compounds and study of expected biological activity,” Res. J. Pharm. Technol., vol. 8, no. 9, pp. 1225–1242, 2015. DOI: https://doi.org/10.5958/0974-360X.2015.00224.3
- D. E. Taha, A. M. R. Raauf, and K. F. Ali, “Design, Synthesis, Characterization, Biological Activity and ADME Study of New 5-arylidene-4-Thiazolidinones Derivatives Having,” Al Mustansiriyah J. Pharm. Sci., vol. 19, no. 4, pp. 77–88, 2019. DOI: https://doi.org/10.32947/ajps.v19i4.637
- Y. Liu et al., “6-OH-phenanthroquinolizidine alkaloid and its derivatives exert potent anticancer activity by delaying S phase progression,” J. Med. Chem., vol. 60, no. 7, pp. 2764–2779, 2017. DOI: https://doi.org/10.1021/acs.jmedchem.6b01502
- A. A. Hamed, I. A. Abdelhamid, G. R. Saad, N. A. Elkady, and M. Z. Elsabee, “Synthesis, characterization and antimicrobial activity of a novel chitosan Schiff bases based on heterocyclic moieties,” Int. J. Biol. Macromol., vol. 153, pp. 492–501, 2020. DOI: https://doi.org/10.1016/j.ijbiomac.2020.02.302
- G. Mariappan, P. Prabhat, L. Sutharson, J. Banerjee, U. Patangia, and S. Nath, “Synthesis and antidiabetic evaluation of benzothiazole derivatives,” J. Korean Chem. Soc., vol. 56, no. 2, pp. 251–256, 2012. DOI: https://doi.org/10.5012/jkcs.2012.56.2.251
- S. M. Sondhi, R. N. Goyal, A. M. Lahoti, N. Singh, R. Shukla, and R. Raghubir, “Synthesis and biological evaluation of 2-thiopyrimidine derivatives,” Bioorg. Med. Chem., vol. 13, no. 9, pp. 3185–3195, 2005. DOI: https://doi.org/10.1016/j.bmc.2005.02.047
- S. De, B. Aamna, R. Sahu, S. Parida, S. K. Behera, and A. K. Dan, “Seeking heterocyclic scaffolds as antivirals against dengue virus,” Eur. J. Med. Chem., vol. 240, p. 114576, 2022. DOI: https://doi.org/10.1016/j.ejmech.2022.114576
- S. Tighadouini et al., “Synthesis, biochemical characterization, and theoretical studies of novel β-keto-enol pyridine and furan derivatives as potent antifungal agents,” ACS omega, vol. 5, no. 28, pp. 17743–17752, 2020. DOI: https://doi.org/10.1021/acsomega.0c02365
- W. A. M. A. El-Enany et al., “Synthesis and molecular docking of some new bis-thiadiazoles as anti-hypertensive α-blocking agents,” Synth. Commun., vol. 50, no. 1, pp. 85–96, 2020. DOI: https://doi.org/10.1080/00397911.2019.1683207
- M. Krátký, J. Vinšová, and J. Stolaříková, “Antimicrobial activity of rhodanine-3-acetic acid derivatives,” Bioorg. Med. Chem., vol. 25, no. 6, pp. 1839–1845, 2017. DOI: https://doi.org/10.1016/j.bmc.2017.01.045
- Y. Wu et al., “Design and synthesis of biaryloxazolidinone derivatives containing a rhodanine or thiohydantoin moiety as novel antibacterial agents against Gram-positive bacteria,” Bioorg. Med. Chem. Lett., vol. 29, no. 3, pp. 496–502, 2019. DOI: https://doi.org/10.1016/j.bmcl.2018.12.012
- K. Ramkumar et al., “Design, synthesis and structure-activity studies of rhodanine derivatives as HIV-1 integrase inhibitors,” Molecules, vol. 15, no. 6, pp. 3958–3992, 2010. DOI: https://doi.org/10.3390/molecules15063958
- M. Mori et al., “Design, synthesis, SAR and biological investigation of 3-(carboxymethyl) rhodanine and aminothiazole inhibitors of Mycobacterium tuberculosis Zmp1,” Bioorg. Med. Chem. Lett., vol. 28, no. 4, pp. 637–641, 2018. DOI: https://doi.org/10.1016/j.bmcl.2018.01.031
- N. Ergenç et al., “Synthesis and hypnotic activity of new 4‐thiazolidinone and 2‐thioxo‐4, 5‐imidazolidinedione derivatives,” Arch. der Pharm. An Int. J. Pharm. Med. Chem., vol. 332, no. 10, pp. 343–347, 1999. DOI: https://doi.org/10.1002/(SICI)1521-4184(199910)332:10<343::AID-ARDP343>3.3.CO;2-S
- G. Kumar et al., “Discovery of a rhodanine class of compounds as inhibitors of Plasmodium falciparum enoyl-acyl carrier protein reductase,” J. Med. Chem., vol. 50, no. 11, pp. 2665–2675, 2007. DOI: https://doi.org/10.1021/jm061257w
- A. A. Abdulnabi, K. F. Ali, and B. M. Abd Razik, “Synthesis, Characterization, ADME Study and Antimicrobial Evaluation of New 1, 2, 3-triazole Derivatives of 2-phenyl benzimidazole.,” Al Mustansiriyah J. Pharm. Sci., vol. 23, no. 2, pp. 147–157, 2023. DOI: https://doi.org/10.32947/ajps.v23i2.1016
- M. M. M. El-Miligy, A. A. Hazzaa, H. El-Messmary, R. A. Nassra, and S. A. M. El-Hawash, “New hybrid molecules combining benzothiophene or benzofuran with rhodanine as dual COX-1/2 and 5-LOX inhibitors: Synthesis, biological evaluation and docking study,” Bioorg. Chem., vol. 72, pp. 102–115, 2017. DOI: https://doi.org/10.1016/j.bioorg.2017.03.012
- S. Bayindir, C. Caglayan, M. Karaman, and İ. Gülcin, “The green synthesis and molecular docking of novel N-substituted rhodanines as effective inhibitors for carbonic anhydrase and acetylcholinesterase enzymes,” Bioorg. Chem., vol. 90, p. 103096, 2019. DOI: https://doi.org/10.1016/j.bioorg.2019.103096
- K. E. Schemmel, R. S. Padiyara, and J. J. D’Souza, “Aldose reductase inhibitors in the treatment of diabetic peripheral neuropathy: a review,” J. Diabetes Complications, vol. 24, no. 5, pp. 354–360, 2010. DOI: https://doi.org/10.1016/j.jdiacomp.2009.07.005
- L. I. Petlichnaya, “The dual reactivity of 3-aminorhodanine,” Chem. Heterocycl. Compd., vol. 3, no. 2, pp. 521–523, 1967. DOI: https://doi.org/10.1007/BF00481590
- G. Jones, P. Willett, R. C. Glen, A. R. Leach, and R. Taylor, “Development and validation of a genetic algorithm for flexible docking,” J. Mol. Biol., vol. 267, no. 3, pp. 727–748, 1997. DOI: https://doi.org/10.1006/jmbi.1996.0897
- G. Jones, P. Willett, and R. C. Glen, “Molecular recognition of receptor sites using a genetic algorithm with a description of desolvation,” J. Mol. Biol., vol. 245, no. 1, pp. 43–53, 1995. DOI: https://doi.org/10.1016/S0022-2836(95)80037-9
Downloads
Published
How to Cite
Issue
Section
License
Copyright (c) 2024 Noor Alhuda Dakel khalaf , Hiba Ali Hasan , Karima Fadhil Ali, Wesen Adel Mehdi
This work is licensed under a Creative Commons Attribution 4.0 International License.