Synthesis, Cytotoxicity, and Structure Activity Relationship SAR of Novel Azo Substituted Pyrazoles
| Author | Khaled Mohammed Alseud | en |
| Orcid | Khaled Mohammed Alseud [0000-0002-2792-8648] | en |
| Accessioned Date | 2026-06-14T10:43:02Z | |
| Issued Date | 2026-12-31 | en |
| Abstract | Background and Objective: Despite the urgent demand for the discovery of novel anticancer agents, anticancer discovery and development remain limited. Azo-containing compounds have emerged as attractive candidates in the field of anticancer drug discovery due to their distinctive reductive metabolism, which may be exploited to enhance anticancer efficacy and selectivity. Accordingly, increasing attention has been directed toward exploring the therapeutic potential of azo-aromatic scaffolds. Methods: In the present study, condensation reactions between benzoyl acetone and various aromatic diazonium salts were carried out to afford four azo derivatives, namely E-2-4-bromophenyldiazenyl-1-phenylbutane-1,3-dione KA101, E-1-phenyl-2-phenyldiazenylbutane-1,3-dione KA102, E-2-4-methoxyphenyldiazenyl-1-phenylbutane-1,3-dione KA103, and E-2-4-nitrophenyldiazenyl-1-phenylbutane-1,3-dione KA104. Subsequent cyclization of these azo precursors provided the corresponding phenyl pyrazole derivatives, designated KA5, KA6, KA7, and KA8, respectively Results: Previously, KA5 exhibited promising anticancer activity against the human hepatocellular carcinoma cell line HepG2. The biological evaluation demonstrated that the newly synthesized KA7 is more potent than KA5, indicating that compounds exhibiting a higher propensity to exist in the hydrazone tautomeric form, particularly KA5 and KA7, showed enhanced cytotoxic activity against HepG2 cells compared with other analogues. Conclusions: These findings demonstrate that both pyrazole ring formation and tautomeric preference significantly influence anticancer activity, supporting azo-pyrazole scaffolds as promising leads for further optimization in anticancer drug development. | en |
| DOI | https://doi.org/10.5812/jrps-167584 | en |
| URI | https://repository.brieflands.com/handle/123456789/67710 | |
| Keyword | Azo Compounds | en |
| Keyword | HepG2 | en |
| Keyword | HSF | en |
| Keyword | Cytotoxicity | en |
| Keyword | Anticancer | en |
| Keyword | Sorafenib | en |
| Publisher | Brieflands | en |
| Title | Synthesis, Cytotoxicity, and Structure Activity Relationship SAR of Novel Azo Substituted Pyrazoles | en |
| Type | Research Article | en |
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