Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety

Castano, Lina; Quiroga, Jairo; Abonı́a, Rodrigo; Insuasty, Daniel; Vidal, Oscar M.; Seña, Rosalia; Rubio, Vivian; Puerto, Gloria; Nogueras, Manuel; Cobo, Justo; Guzman, Juan; Insuasty, Alberto; Insuasty, Braulio

doi:10.3390/ijms232012589

Cited by 15 publications

(6 citation statements)

References 71 publications

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“…When compared to other reported chalcones tested on different melanoma cell lines, we found that compound 12 is two times more active than those of the ethoxy-chalcones class, studied by Harshitha et al [36], where the best derivative showed an IC 50 value of 53.47 µM for A-375 metastatic melanoma cell line. On the other hand, compound 12 was found to be less active than the synthesized chalcone-sulfonamide hybrids reported by Castaño et al [37], most of them possessing activities against LOX IMVI melanoma cell line, with IC 50 values between 0.34 and 0.54 µM.…”

Section: Antimelanoma Activitiesmentioning

confidence: 61%

The Synthesis of 2′-Hydroxychalcones under Ball Mill Conditions and Their Biological Activities

Abid,

Moslah,

Cojean

et al. 2024

Molecules

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Chalcones are polyphenols that belong to the flavonoids family, known for their broad pharmacological properties. They have thus attracted the attention of chemists for their obtention and potential activities. In our study, a library of compounds from 2′-hydroxychalcone’s family was first synthesized. A one-step mechanochemical synthesis via Claisen–Schmidt condensation reaction under ball mill conditions was studied, first in a model reaction between a 5′-fluoro-2′-hydroxyacetophenone and 3,4-dimethoxybenzaldehyde. The reaction was optimized in terms of catalysts, ratio of reagents, reaction time, and influence of additives. Among all assays, we retained the best one, which gave the highest yield of 96% when operating in the presence of 1 + 1 eq. of substituted benzaldehyde and 2 eq. of KOH under two grinding cycles of 30 min. Thus, this protocol was adopted for the synthesis of the selected library of 2′-hydroxychalcones derivatives. The biological activities of 17 compounds were then assessed against Plasmodium falciparum, Leishmania donovani parasite development, as well as IGR-39 melanoma cell lines by inhibiting their viability and proliferation. Compounds 6 and 11 are the most potent against L. donovani, exhibiting IC50 values of 2.33 µM and 2.82 µM, respectively, better than the reference drug Miltefosine (3.66 µM). Compound 15 presented the most interesting antimalarial activity against the 3D7 strain, with IC50 = 3.21 µM. Finally, chalcone 12 gave the best result against IGR-39 melanoma cell lines, with an IC50 value of 12 µM better than the reference drug Dacarbazine (IC50 = 25 µM).

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Section: Antimelanoma Activitiesmentioning

confidence: 61%

The Synthesis of 2′-Hydroxychalcones under Ball Mill Conditions and Their Biological Activities

Abid,

Moslah,

Cojean

et al. 2024

Molecules

View full text Add to dashboard Cite

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“…Castano and collaborators (2022) [ 74 ], synthesized chalcone-sulfonamide hybrids. Since the compound ( 67 ) ( Figure 13 ) presented the best inhibition profile for LOX IMVI (melanoma) with IC50 = 0.34 µM, it also showed good results for MCF7 and MDA-MB-468 (breast cancer) with IC50 values of 0.97 and 1.20 µM, respectively; K-562 (leukemia) with IC50 = 1.50 µM, and HCT-116 (colon cancer) with IC50 = 1.49 µM.…”

Section: Chalcones With Anticancer Activitymentioning

confidence: 99%

Anticancer Activity of Chalcones and Its Derivatives: Review and In Silico Studies

et al. 2023

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Chalcones are direct precursors in the biosynthesis of flavonoids. They have an α,β-unsaturated carbonyl system which gives them broad biological properties. Among the biological properties exerted by chalcones, their ability to suppress tumors stands out, in addition to their low toxicity. In this perspective, the present work explores the role of natural and synthetic chalcones and their anticancer activity in vitro reported in the last four years from 2019 to 2023. Moreover, we carried out a partial least square (PLS) analysis of the biologic data reported for colon adenocarcinoma lineage HCT-116. Information was obtained from the Web of Science database. Our in silico analysis identified that the presence of polar radicals such as hydroxyl and methoxyl contributed to the anticancer activity of chalcones derivatives. We hope that the data presented in this work will help researchers to develop effective drugs to inhibit colon adenocarcinoma in future works.

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“…Scientific groups have reported on the successful implementation of the hybrid pharmacophore concept, which is performed through combining heterocycles with recognized active groups like sulfonamides [ 42 , 43 ]. Hybridized heterocycles with sulfonamides were successfully applied in the reported literature as seen in the interconnection between phthalazinone derivatives and sulfonamides as sulfadiazine and sulfathiazole, which was a successful strategy to synthesize broad-spectrum antibacterial compounds [ 28 ].…”

Section: Introductionmentioning

confidence: 99%

Antimicrobial Evaluation of Sulfonamides after Coupling with Thienopyrimidine Coplanar Structure

Elmongy,

Alanazi,

Aldawsari

et al. 2024

Pharmaceuticals

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This work describes the design and synthesis of three series of hybrids of thienopyrimidines and sulfonamides. Dihydrofolate reductase enzyme was selected as a target for the in-silico screening of the synthesized thienopyrimidine–sulfonamide hybrid as an antibacterial, while squalene epoxidase was selected as an antifungal target protein. All screened compounds showed promising binding affinity ranges, with perfect fitting not exceeding 1.9 Å. The synthesized compounds were tested for their antimicrobial activity using agar well diffusion and minimum inhibitory concentration tests against six bacterial strains in addition to two Candida strains. Compounds 8iii and 12ii showed varying degrees of inhibition against Staphylococcus aureus and Escherichia coli bacterial strains, whereas the best antifungal activity against Candida was displayed by compound 8iii. Compound 12ii, the cyclohexathienopyrimidine coupled with sulfadiazine at position 3, has the best antibacterial activity, which is consistent with molecular docking results at the active site of the oxidoreductase protein. Interestingly, compound 12ii also has the highest docking binding energy at the antifungal squalene epoxidase active site. Investigating the physicochemical properties of the synthesized hybrids revealed their high tolerability with cell membranes, and moderate to poor oral bioavailability, and that all are drug-like candidates, among which 4i, the cyclohexathieno[2,3-d] pyrimidine core with sulphaguanidine incorporated at position 4, recorded the best score (1.58).

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Synthesis, Anticancer and Antitubercular Properties of New Chalcones and Their Nitrogen-Containing Five-Membered Heterocyclic Hybrids Bearing Sulfonamide Moiety

Cited by 15 publications

References 71 publications

The Synthesis of 2′-Hydroxychalcones under Ball Mill Conditions and Their Biological Activities

The Synthesis of 2′-Hydroxychalcones under Ball Mill Conditions and Their Biological Activities

Anticancer Activity of Chalcones and Its Derivatives: Review and In Silico Studies

Antimicrobial Evaluation of Sulfonamides after Coupling with Thienopyrimidine Coplanar Structure

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