1,982
Views
9
CrossRef citations to date
0
Altmetric
Research Papers

Novel 3-(6-methylpyridin-2-yl)coumarin-based chalcones as selective inhibitors of cancer-related carbonic anhydrases IX and XII endowed with anti-proliferative activity

ORCID Icon, ORCID Icon, ORCID Icon, , , , ORCID Icon & ORCID Icon show all
Pages 1043-1052 | Received 22 Feb 2022, Accepted 18 Mar 2022, Published online: 19 Apr 2022

Figures & data

Figure 1. Structure of coumarin I, its hydrolysed form II, some reported coumarin-based CAIs III–V, some reported pyridine derivatives bearing chalcone functionality VI–IX, and target compounds 5a–o.

Figure 1. Structure of coumarin I, its hydrolysed form II, some reported coumarin-based CAIs III–V, some reported pyridine derivatives bearing chalcone functionality VI–IX, and target compounds 5a–o.

Scheme 1. Reagents and conditions: (i) Dry toluene, reflux 7 h.; (ii) Acetylacetone, CH3COONH4, AcOH, reflux 10 h.

Scheme 1. Reagents and conditions: (i) Dry toluene, reflux 7 h.; (ii) Acetylacetone, CH3COONH4, AcOH, reflux 10 h.

Scheme 2. Reagents and conditions: (i) KOH (aq.), dioxane: MeOH stirring at 0 °C 2 h then r.t overnight.

Scheme 2. Reagents and conditions: (i) KOH (aq.), dioxane: MeOH stirring at 0 °C 2 h then r.t overnight.

Table 1. Inhibition data of MPC 3 and 5a–o against hCA isoforms I, II, IX, and XII using AAZ as a reference.

Table 2. Selectivity ratios for MPC 3 and MPCs 5a–o towards cancer-related hCA isoforms.

Table 3. Cell growth inhibition (GI%) of 59 human tumour cell lines in vitro at a dose of 10 µM for MPCs 5g and 5l.

Figure 2. The best anti-proliferative activities exerted by target MPC chalcones 5a–f, 5h–k, and 5m–o.

Figure 2. The best anti-proliferative activities exerted by target MPC chalcones 5a–f, 5h–k, and 5m–o.

Table 4. Results of the five-dose anticancer assay for MPC 5l against all fifty-nine cancer cell lines.

Supplemental material

Supplemental Material

Download PDF (8.3 MB)