Unknown

Dataset Information

0

Design, Synthesis and Biological Evaluation of Aromatase Inhibitors Based on Sulfonates and Sulfonamides of Resveratrol.

ABSTRACT: A library of sulfonate and sulfonamide derivatives of Resveratrol was synthesized and tested for its aromatase inhibitory potential. Interestingly, sulfonate derivatives were found to be more active than sulfonamide bioisosteres with IC50 values in the low micromolar range. The sulfonate analogues 1b-c and 1j exhibited good in vitro antiproliferative activity on the MCF7 cell line, evidenced by MTT and LDH release assays. Structure-activity relationships suggested that electronic and lipophilic properties could have a different role in promoting the biological response for sulfonates and sulfonamides, respectively. Docking studies disclosed the main interactions at a molecular level of detail behind the observed inhibition of the more active compounds whose chemical stability has been evaluated with nano-liquid chromatography. Finally, 1b-c and 1j were highlighted as sulfonates to be further developed as novel and original aromatase inhibitors.

SUBMITTER: Fantacuzzi M 

PROVIDER: S-EPMC8537897 | biostudies-literature | 2021 Sep

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

Design, Synthesis and Biological Evaluation of Aromatase Inhibitors Based on Sulfonates and Sulfonamides of Resveratrol.

Fantacuzzi Marialuigia M   Gallorini Marialucia M   Gambacorta Nicola N   Ammazzalorso Alessandra A   Aturki Zeineb Z   Balaha Marwa M   Carradori Simone S   Giampietro Letizia L   Maccallini Cristina C   Cataldi Amelia A   Nicolotti Orazio O   Amoroso Rosa R   De Filippis Barbara B  

Pharmaceuticals (Basel, Switzerland) 20210927 10

A library of sulfonate and sulfonamide derivatives of Resveratrol was synthesized and tested for its aromatase inhibitory potential. Interestingly, sulfonate derivatives were found to be more active than sulfonamide bioisosteres with IC<sub>50</sub> values in the low micromolar range. The sulfonate analogues <b>1b</b>-<b>c</b> and <b>1j</b> exhibited good in vitro antiproliferative activity on the MCF7 cell line, evidenced by MTT and LDH release assays. Structure-activity relationships suggested  ...[more]

Similar Datasets

Unknown Design, synthesis, and biological evaluation of resveratrol analogues as aromatase and quinone reductase 2 inhibitors for chemoprevention of cancer.
| S-EPMC2903642 | biostudies-literature
Unknown Design, Synthesis, and Biological Evaluation of Novel 1,3-Oxazole Sulfonamides as Tubulin Polymerization Inhibitors.
| S-EPMC8201758 | biostudies-literature
Unknown Design, Synthesis, and Biological Evaluation of Apcin-Based CDC20 Inhibitors.
| S-EPMC8842116 | biostudies-literature
Unknown Design, synthesis and biological evaluation of erlotinib-based IDO1 inhibitors
| S-EPMC9399373 | biostudies-literature
Unknown Development of benzofuran-derived sulfamates as dual aromatase-steroid sulfatase inhibitors (DASIs): design, synthesis and biological evaluation.
| S-EPMC11792066 | biostudies-literature
Unknown Design, synthesis, biological and structural evaluation of functionalized resveratrol analogues as inhibitors of quinone reductase 2.
| S-EPMC3804415 | biostudies-literature
Unknown Structure-Based Design, Synthesis, and Biological Evaluation of Triazole-Based smHDAC8 Inhibitors.
| S-EPMC7187165 | biostudies-literature
Unknown Structure-Based Design, Synthesis, and Biological Evaluation of Hsp90β-Selective Inhibitors.
| S-EPMC8790780 | biostudies-literature
Unknown Novel Anthranilamide-Based FXa Inhibitors: Drug Design, Synthesis and Biological Evaluation.
| S-EPMC6274369 | biostudies-literature
Unknown Structure-based design, synthesis, and biological evaluation of peptidomimetic SARS-CoV 3CLpro inhibitors.
| S-EPMC2112940 | biostudies-other