1,4-Disubstituted bis-chromenyl triazole hybrids 5a-m have been synthesized in a three-step reaction sequence from 4-(bromomethyl)-2H-chromen-2-ones 3a-m. The intermediate azides 4a-m underwent a regioselective 1,3-dipolar cycloaddition with a 2H-chromen-2-one linked acetylenic dipolarophile in the presence of Cu (II)/ascorbate/ water/n-butanol reaction medium. Three compounds 5h-j exhibited 6.25 lg/mL MIC against M. tuberculosis. Among the compounds screened for antifungal activity, lowest MIC of 6.25 lg/mL was observed for 5c against A. niger that also exhibited DNA cleavage observed by agarose gel electrophoresis. All the compounds were moderately active against both Gram-positive and Gramnegative bacterial strains. The cytotoxic effect of potent compounds on normal cells (V79 and HBL100) was assessed by MTT assay.
Abstract.A new synthetic strategy for the construction of dihydrofuro coumarins and quinolones has been developed by a three component reaction. Formation of 2,3-dihydrofuran ring and the trans orientation is supported by 1 H-NMR and confirmed single X-ray diffraction studies.
A Click Chemistry Approach for the Synthesis of Mono and Bis Aryloxy Linked Coumarinyl Triazoles as Antitubercular Agents. -A wide range of mono-and bis-triazole coumarin hybrids are formed from chromene-2-one derivatives and propargyl ethers employing a Click chemistry modified protocol for Azide-Alkyne cycloadditions. The antitubercular screening shows moderate activities for the mono aryloxy compounds (III) and significant activities for compounds (V). Bis-derivative (Va) shows the highest activity. -(ANAND, A.; NAIK, R. J.; REVANKAR, H. M.; KULKARNI*, M. V.; DIXIT, S. R.; JOSHI, S. D.; Eur. J. Med. Chem. 105 (2015) 194-207, http://dx.
In the title compound, C15H19NO5, an intramolecular O—H⋯O hydrogen bond links the hydroxyethyl side chains, forming a seven-membered ring. In the crystal, molecules are linked into chains via O—H⋯O hydrogen bonds along the b axis. Further, molecules are linked by weak intermolecular C—H⋯O and π–π stacking interactions [centroid–centroid distance = 3.707 (4) Å].
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