864717-03-3Relevant articles and documents
Cross-Coupling of Amide and Amide Derivatives to Umbelliferone Nonaflates: Synthesis of Coumarin Derivatives and Fluorescent Materials
Hickey, Shane M.,Nitschke, Samuel O.,Sweetman, Martin J.,Sumby, Christopher J.,Brooks, Douglas A.,Plush, Sally E.,Ashton, Trent D.
, p. 7986 - 7999 (2020)
The Buchwald-Hartwig cross-coupling reaction between 4-methylumbelliferone-derived nonaflates with amides, carbamates, and sulfonamides is described. A wide variety of N-substituted 7-amino coumarin analogues was prepared in good to excellent yields. The photophysical properties of aqueous-soluble derivatives were determined, and they displayed auxochrome-based variations. Gram-scale synthesis provided an acrylamide analogue, which was used to fabricate a fluorescent poly(2-hydroxylethyl methacrylate) (pHEMA) hydrogel that was resistant to leaching in ultrapure H2O. We envisage that our reported protocol to access 7-amino-4-methylcoumarin derivatives will find use toward the development of new fluorescent coumarin-based probes by researchers in the field.
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.
