Synthesis and antimalarial activity of sulfonamide chalcone derivatives

Domínguez, José N.; León, Caritza; Rodrígues, Juan; Domínguez, Neira Gamboa de; Gut, Jiří; Rosenthal, Philip J.

doi:10.1016/j.farmac.2005.01.005

Cited by 149 publications

(77 citation statements)

References 16 publications

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“…Chalcones possess a wide range of biological activities such as antibacterial 32 , antifungal 32 , antiviral 33 , antifeedant 3,29 , anticancer 34 , antimalarial 35 , antituberclosis 28 , antiAIDS 36 and antioxidant 37 activities. These multipronged activities present in different chalcones are examined against respective microbes-bacteria's and fungi.…”

Section: Microbial Activitiesmentioning

confidence: 99%

Preheated Fly-Ash Catalyzed Aldol Condensation: Efficient Synthesis of Chalcones and Antimicrobial Activities of Some 3-Thienyl Chalcones

Arulkumaran¹,

Vijayakumar²,

Sakthinathan³

et al. 2013

J. Chil. Chem. Soc.

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Section: Microbial Activitiesmentioning

confidence: 99%

Preheated Fly-Ash Catalyzed Aldol Condensation: Efficient Synthesis of Chalcones and Antimicrobial Activities of Some 3-Thienyl Chalcones

Arulkumaran¹,

Vijayakumar²,

Sakthinathan³

et al. 2013

J. Chil. Chem. Soc.

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“…Soc. 886 are already known, [35][36][37][38][39] even though their crystal structures have not been elucidated thus far. The nuclear magnetic resonance (NMR) data of two of these compounds (4 and 5) is also new (see Supplementary Information).…”

Section: Introductionmentioning

confidence: 99%

Conformational Variability in Sulfonamide Chalcone Hybrids: Crystal Structure and Cytotoxicity

Castro¹,

Aragão²,

Silva³

et al. 2015

Journal of the Brazilian Chemical Society

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Four sulfonamide-chalcone derivatives were prepared and their crystal structure were elucidated by single-crystal X-ray diffraction technique. They were synthesized by Claisen-Schmidt condensation reaction between N-(4-acetylphenyl)benzenesulfonamide or N-(4-acetylphenyl)-2,5-dichlorobenzenesulfonamide with benzaldehyde or p-nitrobenzaldehyde. Values of Z' > 1 are found in three compounds as a consequence of conformerism. The chalcone molecular backbones are featured by different levels of planarity in their conformers. Another conformational variability is in its benzenesulfonamide moiety. In the compound came from N-(4-acetylphenyl) benzenesulfonamide and benzaldehyde, there is a rotation of ca. 180° on the bond axis bridging the sulfonamide and chalcone motifs of one conformer if the two others are taken as references. The cytotoxic activity of all compounds synthesized here and of two other related sulfonamide chalcones was also assessed against three cancer cell lines (SF-295, HCT-8 and MDA-MB-435). The para-nitro compounds were the most active ones among all those tested, regardless of substitution pattern in benzenesulfonamide core.

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“…[9,10] Sulfonamides represent an important class of medically important compound, which is present in a number of biologically active molecules. In addition, sulfonamide derivatives are extensively used as antitumor, [11,12] antiviral, [13] antimalarial, [14,15] anti-inflammatory, [16] anticancer, [17] anti-carbonic anhydrase, [18] antidiabetic agents, [19] and in Alzheimer's diseases. [20] Computer-aided structure-based rational drug designing have the potential not only of speeding up the drug discovery process thus reducing the costs, but also of changing the way drugs are designed.…”

Section: Introductionmentioning

confidence: 99%

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2017

AJP

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Aims: Malaria remains a worldwide health problem. Resistance to antimalarial drugs by the Plasmodium falciparum malaria parasite is posing a serious impediment in malaria control program. Hence continuous efforts on the development of new antimalarial are required. Being an important enzyme in parasite physiology diadenosine tetraphosphate (Ap4A) hydrolase may prove a good target for antimalarial drugs. The aim of this study was to explore the inhibitory potential of some sulfonamide derivatives against malaria parasite Ap4A hydrolase. Materials and Methods: The molecular three-dimensional structural data of malaria parasite Ap4A hydrolase were obtained from protein databank (PDB ID: 5CFI) and used as a drug target. The molecular docking approach was employed to find out the in silico inhibitory potential of the sulfonamide derivatives against Ap4A hydrolase and their relative stabilities were studied. Results and Discussion: All sulfonamide derivatives showed good binding affinity against the target protein. The binding free energy of compound 4-amino-N-(quinoxalin-2yl) benzenesulfonamide S6 (−8.43 Kcal/mole) showed it to be the most optimal sulfonamide derivative as inhibitor for Ap4A hydrolase enzyme. Conclusions: Evaluation of binding affinities using free energy simulations allowed establishing that sulfonamides having quinoxaline moiety is the highest quality compound of the series. The findings attained through this study on the molecular interaction mode of sulfonamide derivatives, and Ap4A hydrolase enzyme can be considered for further in vitro and in vivo validation for designing new potential antimalarial drugs.

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Synthesis and antimalarial activity of sulfonamide chalcone derivatives

Cited by 149 publications

References 16 publications

Preheated Fly-Ash Catalyzed Aldol Condensation: Efficient Synthesis of Chalcones and Antimicrobial Activities of Some 3-Thienyl Chalcones

Preheated Fly-Ash Catalyzed Aldol Condensation: Efficient Synthesis of Chalcones and Antimicrobial Activities of Some 3-Thienyl Chalcones

Conformational Variability in Sulfonamide Chalcone Hybrids: Crystal Structure and Cytotoxicity

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