Synthesis and antiproliferative activity of new 2-glyco-3-nitro-2H-chromenes

Abstract

3-nitro-2H-chromenes and derivatives are compounds with diverse biological activity, among them, new 2-glyco-3-nitro-2H-chromenes have been prepared by one-pot oxa-Michael-Henrydehydration reactions between carbohydrate-derived nitroalkenes and several salicylaldehydes, using a minimal amount of solvent and DBU as catalyst. The antiproliferative activity of these new compounds has been evaluated against a panel of six human solid tumor cell lines, and compared to pharmacological reference compounds, finding that their activities are in the low micromolar range and that some of them are more effective than the standards.

2H/4H-Chromenes—A Versatile Biologically Attractive Scaffold

“…Also, a series of newly 2-glyco-3-nitro-2H-chromenes were synthesized Luque-Agudo et al ( 2019 ) using oxo-Michael-Henry-dehydration reactions and tested for their activity against the cancer cell lines. Regarding cancer cell line inhibition, compounds 34 , 35 , 36 , and 39 [growth inhibitory 50% (GI 50 ) 1.9, 1.7, 2.6, and 3.1 μM, respectively] displayed good GI 50 against the WiDr multidrug resistance cells.…”

“…These findings may be helpful to the future study involving the use of selective target inhibition in cancer. Although the mixture of 35+38 and 36+37 has been identified as a potent inhibitor of the targeted cell line, these compounds should be tested for their anticancer potency over in-vivo cancer (Luque-Agudo et al, 2019 ).…”

“…A series of new 2-glyco-3-nitro-2H-chromenes for anticancer activity were reported by Luque-Agudo et al ( 2019 ). The SAR of these series of compounds were constructed that 2H ch was an important motif for the development of anticancer lead molecule ( Figure 9D ).…”

“…One of the essential structural features of 4H-ch to impart miscellaneous activity is the occurrence of the fold along the oxygen axis. The molecules containing 2H/4H-ch scaffold exhibit noteworthy potency, such as anticancer (Afifi et al, 2017a ; Halawa et al, 2017 ; Elshaflu et al, 2018 ; Elnaggar et al, 2019 ; Luque-Agudo et al, 2019 ), anticonvulsant (Rawat and Verma, 2016 ), antimicrobial (Suvarna et al, 2017 ; Mashhadinezhad et al, 2019 ), anticholinesterase (Tehrani et al, 2019 ), antidiabetic activities (Soni et al, 2019 ), antituberculosis (Zhao et al, 2020 ), and inhibitory activity against monoamine oxidase (MAO) (Takao et al, 2019 ).…”

“…Therefore, these molecules target and interrupt tumor vasculature (Anthony et al, 2007 ). Some analogs of 2H/4H-ch triggered the cell apoptosis by the caspse3/7 activation and executioner of DNA fragmentation and also caused a substantial reduction in the cell invasion and cell migration percentage (Alblewi et al, 2019a ; Luque-Agudo et al, 2019 ). Additionally, the potency of substituted-1H-benzimidazol-2-yl fused with 4H-chromen-4-ones analogs was reported, which revealed that 4H-ch analogs were selective inhibitors of formyl peptide receptor-1 (FPR-1), led to blocking the Ca 2+ flux and inhibited chemotaxis in human neutrophils (Schepetkin et al, 2014 ).…”