An article Methoxychalcones: Effect of Methoxyl Group on the Antifungal Antibacterial and Antiproliferative Activities WOS:000589443500004 published article about CHALCONE DERIVATIVES; BIOLOGICAL-ACTIVITIES; MOLECULAR-PROPERTIES; LICOCHALCONE; PREDICTION; DISCOVERY; GROWTH; SERIES; AGENTS in [Marques, Beatriz C.; Santos, Mariana B.; Anselmo, Daiane B.; Regasini, Luis O.] Sao Paulo State Univ Unesp, Inst Biosci Humanities & Exact Sci, Dept Chem & Environm Sci, BR-15054000 Sao Jose Do Rio Preto, SP, Brazil; [Monteiro, Diego A.; Gomes, Eleni; Saiki, Marilia F. C.; Rahal, Paula] Sao Paulo State Univ Unesp, Inst Biosci Humanities & Exact Sci, Dept Biol, BR-15054000 Sao Jose Do Rio Preto, SP, Brazil; [Rosalen, Pedro L.; Sardi, Janaina C. O.] Univ Campinas Unicamp, Piracicaba Dent Sch, Dept Physiol Sci, BR-13083970 Piracicaba, SP, Brazil in 2020.0, Cited 43.0. Safety of 2,5-Dimethoxybenzaldehyde. The Name is 2,5-Dimethoxybenzaldehyde. Through research, I have a further understanding and discovery of 93-02-7
Background: Chalcones substituted by methoxyl groups have presented a broad spectrum of bioactivities, including antifungal, antibacterial and antiproliferative effects. However, a clear and unambiguous investigation about the relevance of this substituent on the chalcone framework has not been described. Objective: The purpose of this work is to assess the antibacterial, antifungal and antiproliferative activities of the two series of seventeen synthesized regioisomeric methoxychalcones. Series I and II were constituted by cbalcones substituted by methoxyl groups on rings A (5-12) and B (13-21), respectively. In addition, the library of methoxychalcones was submitted to in silico drug-likeness and pharmacokinetics properties predictions. Methods: Methoxychalcones were synthesized and their structures were confirmed by NMR spectral data analyses. Evaluations of antimicrobial activity were performed against five species of Candida, two Gram-negative and five Gram-positive species. For antiproliferative activity, methoxychalcones were evaluated against four human tumorigenic cell lines, as well as human non-tumorigenic keratinocytes. Drug-likeness and pharmacokinetics properties were predicted using Molinspiration and PreADMET toolkits. Results: In general, chalcones of series I are the most potent antifungal, antibacterial and antiproliferative agents. 3′, 4′, 5′-Trimethoxychalcone (12) demonstrated potent antifungal activity against Candida krusei (MIC = 3.9 mu g/mL), eight times more potent than fluconazole (reference antifungal drug). 3′-Methoxychalcone (6) displayed anti-Pseudomonas activity (MIC = 7.8 mu g/mL). 2′,5′-Dimethoxychalcone (9) displayed potent antiproliferative effect against C-33A (cervix), A-431 (skin) and MCF-7 (breast), with IC50 values ranging from 7.7 to 9.2 mu M. Its potency was superior to curcumin (reference antiproliferative compound), which exhibited IC50 values ranging from 10.4 to 19.0 mu M. Conclusion: Our studies corroborated the relevance of methoxychalcones as antifungal, antibacterial and antiproliferative agents. In addition, we elucidated influence of the position and number of methoxyl groups toward bioactivity. In silico predictions indicated good drug-likeness and pharmacokinetics properties to the library of methoxychalcones.
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