461691-03-2Relevant academic research and scientific papers
New coumarin/sulfocoumarin linked phenylacrylamides as selective transmembrane carbonic anhydrase inhibitors: Synthesis and in-vitro biological evaluation
Angeli, Andrea,Arifuddin, Mohammed,Singh, Priti,Supuran, Claudiu T.,Swain, Baijayantimala
, (2020)
Two novel series of phenylacrylamide linked coumarins and sulfocoumarins (6a-p, 8a-i, and 14a-g) were synthesized and evaluated against four physiologically relevant human carbonic anhydrases (hCAs, EC 4.2.1.1), isoforms hCA I, hCA II, hCA IX and hCA XII for their inhibitory action. All new compounds when screened for carbonic anhydrase inhibitory activity have shown selective inhibition towards the tumor associated isoforms hCA IX and XII over CA I and II, with inhibition constants in the submicromolar to low nanomolar range. Compound 6b and 14g exhibited significant inhibition with low nanomolar potency against hCA IX, whereas 6k was effective against hCA XII. Compounds 6b, 14g and 6k may be considered as lead molecules for future development of cancer therapeutics based on a novel mechanism of action.
Synthesis and evaluation of antiinflammatory and analgesic activities of a novel series of substituted-N-(4-methyl-2-oxo-2H-chromen-7-yl) benzamides
Ronad, Pradeepkumar M.,Hunashal, Rajesh D.,Darbhamalla, Satyanarayana,Maddi, Veeresh S.
experimental part, p. 641 - 646 (2009/04/10)
A novel series of coumarinyl amides (IVa-1) have been synthesized by reacting 7-amino-4-methylcoumarin (III) with various substituted aromatic acid chlorides. IR, 1H NMR, 13C NMR and HRMS spectral data characterized the structure of the synthesized compounds. The title compounds were screened for in vivo acute anti-inflammatory activity using the carrageenan-induced rat paw edema assay model. Among the compounds tested, 2-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)benzamide (IVb) and 4-chloro-N-(4-methyl-2-oxo-2H-chromen-7-yl)benzamide (IVc) showed 60.5 and 62.3% edema protection, respectively, as compared to the standard drug diclofenac (CAS 15307-86-5) (63.5%) after third hour. Compounds N-(4-methyl-2-oxo-2H- chromen-7-yl)-4-nitrobenzamide (IVf) and N-(4-methyl-2-oxo-2H-chromen-7-yl) cinnamamide (IVg) showed moderate activity. The new compounds have been also tested for in vivo analgesic activity. Quantitative structure-activity relationship studies indicated that the chloro substitution at the aromatic ring enhanced the anti-inflammatory activity (IVb and IVc). These compounds were also found to provide significant protection in acetic acid induced writhing animal model, showing remarkable analgesic activity. Compounds IVb and IVc showed 55.1% and 56.3% protection, respectively, as compared to acetylsalicylic acid (CAS 50-78-2) (57.7%). ECV - Editio Cantor Verlag.
