Multicomponent reaction protocol has been developed for the synthesis of novel pyrimidine fused pyrazolo [3,4-b]pyridine derivatives (7 a-g) and hexahydroquinazoline fused pyrazolo [3,4-b] pyridine derivatives (8 a-i) starting from 3-amino-5carbethoxy-6-trifluoromethyl pyrazolo[3,4-b] pyridine 5. All the synthesized compounds were evaluated for antibacterial as well as antifungal activities and compounds 7 f, 8 a, 8 c and 8 d exhibited promising antibacterial activity. In particular, compound 2,4,6-trifluoro substituted pyrimidine fused pyrazolo [3,4-b]pyridine (7 f) showed very good antibacterial activity against the panel of both Gram-positive and -negative bacterial strains. Hexahydroquinazoline fused pyrazolo [3,4-b]pyridine derivatives (8 f-i) also showed promising antifungal activity and broadspectrum anti-biofilm activity against both Gram-positive and negative bacterial strains. The crystal structure of compound 8 b was solved based on single crystal X-ray diffraction study. Docking studies were performed to identify the interactions of the compounds 7 f with crtM enzyme of Staphylococcus aureus.
An unprecedented Domino transformation towards diverse fluorinated spiro benzothiazinyl furanone scaffolds has been developed from 1,3‐diketone embedded benzothiazines and Selectfluor through fluorinative intramolecular cyclization. The transformation is triggered by fluorine insertion to form a difluoro intermediate, which is responsible for the formation of fluorinated spiro 3(2H)‐furanone derivatives. We have also succeeded to synthesize non‐fluorinated spiro 3(2H)‐furanone derivatives by oxidative cyclization using AgF.
Aus der Curbonsäure (I) wird über die Zwischenstufen (ll)‐(lX) die DimethylallyI‐Verbindung (X) hergestellt, die mit dem Aldehyd (XI) zu den Benzodipyranonen (XII) und (XIII) umgesetzt wird.
A series of novel 1,2‐benzothiazine‐1,1‐dioxide derivatives (Z)‐3‐hydroxy‐1‐(4‐hydroxy‐2‐methyl‐1,1‐dioxido‐2H‐benzo[e][1, 2]thiazin‐3‐yl)‐3‐phenyl substituted prop‐2‐en‐1‐one (6 a‐d) were synthesized starting from sodium salt of saccharin 1 in series of steps via 3‐acetyl‐2‐methyl‐1,1‐dioxido‐2H‐benzo[e][1, 2]thiazin‐4‐yl substituted benzoates (5 a‐d). Compound 6 e was obtained alternately from 1‐(4‐Hydroxy‐2‐methyl‐1,1‐dioxo‐1,2‐dihydro‐1λ6‐benzo[e][1, 2]thiazin‐3‐yl)‐ethanone (4). Compounds 6 a‐e were further reacted with aromatic azides to form (4‐hydroxy‐2‐methyl‐1,1‐dioxido‐2H‐benzo[e][1, 2]thiazin‐3‐yl)(1‐substitutedphenyl)‐5‐ substituted pheny or methyl‐1H‐1,2,3‐triazol‐4‐yl)methanone derivatives (7 a‐o) by regioselective cyclization. All the compounds were evaluated for anti‐inflammatory and anti‐cancer activities. Compounds 5 a‐b, 6 a‐b, 7 a, 7 c‐d, 7 i and 7 k‐l which showed significant anti‐inflammatory activity at micro molar concentration have been identified. Also screened for cytotoxic activity against four human cancer cells and one normal cell such as prostate cancer (PC‐3), breast adenocarcinoma (MDA‐MB‐231), liver hepatocellular carcinoma (Hep G2), cervical cancer (HeLa) and normal umbilical vein endothelial cell (HUVEC). Compounds 6 a, 7 g, 7 h and 7 k have been identified as promising candidates. Further, anti‐inflammatory activity is also validated by docking studies and compounds 5 a, 5 b and 7 d found to show good interactions when docked with IL‐1β signaling complex.
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