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Cu-promoted synthesis of Indolo[2,3-b]quinoxaline-Mannich adducts via three-component reaction and their anti-proliferative evaluation on colorectal and ovarian cancer cells.
- Source :
-
Journal of Molecular Structure . Mar2023, Vol. 1275, pN.PAG-N.PAG. 1p. - Publication Year :
- 2023
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Abstract
- • Cu-promoted synthesis of indolo [2,3- b ]quinoxaline-Mannich adducts. • The anti-proliferative activities were assessed on OVCAR-3 and HT-29 cells. • The promising compounds exhibited caspase-mediated apoptotic cell death. • The promising compounds were further studied in silico using the crystal structure of c-Met-kinase. The present work intends to synthesize a new class of small molecules featuring the quinoxaline scaffold. The indolo [2,3- b ]quinoxaline-Mannich adducts were designed, synthesized and their anticancer activities were tested using MTS assay against human ovarian cancer (OVCAR-3) and female colorectal adenocarcinoma cancer cell lines (HT-29). Compounds 6q and 6r efficiently inhibited both cancer cell lines tested, with IC 50 values of 58.57 and 55.90 µM against OVCAR-3 and 31.36 and 42.3 µM against HT-29, respectively. The evaluation results were further supported by caspase-mediated apoptosis and docking studies, which indicated that Tyr1159 and the N-atom of the pyrrolidine moiety formed an additional hydrogen bond that stabilised the c-Met-kinase-6q complex. Overall, the results of our study suggested that Mannich-inspired indolo [2,3- b ]quinoxaline adduct might make interesting lead for the development of cancer chemotherapeutics. Synthesis and anti-proliferative evaluation of Indolo [2,3- b ]quinoxaline-Mannich adducts [Display omitted] [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00222860
- Volume :
- 1275
- Database :
- Academic Search Index
- Journal :
- Journal of Molecular Structure
- Publication Type :
- Academic Journal
- Accession number :
- 161100475
- Full Text :
- https://doi.org/10.1016/j.molstruc.2022.134627