Acylation of oxazolo[4,5-b]pyridin-2(3H)-ones, 2-phenyloxazolo[4,5-b]pyridines and pyrrolo[2,3-b]pyridin-2(2H)-ones

Marie-Claude, Viaud; Jamoneau, P.; Marie-Laure, Baudin; Savelon, L.; Guillaumet, Gérald

doi:10.1016/s0040-4020(97)00179-8

Cited by 18 publications

(2 citation statements)

References 8 publications

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“…[3] Its pharmacological activities also include anti-pyretic, anti-inflammatory, analgesic [4] and antifungal properties. [5] These compounds also find their application as pesticides [6] and dyes.…”

Section: Introductionmentioning

confidence: 99%

Acid-Catalyzed, Silica-Supported, One-Pot Benzoylation Route to Synthesize 2-(Substituted Phenyl)oxazolo[4,5-b]pyridines Under Ambient Conditions

Reen

Dudhe

Ahuja

et al. 2015

Synthetic Communications

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Present paper elicits the silica supported perchloric acid catalyzed efficient protocol for the synthesis of 2-(phenyl)oxazolo[4,5-b]pyridine derivatives. The remarkable feature of this strategy embraces the high conversion, simple work-up procedures, ambient conditions, short reaction time and reusability of the catalyst. Structures of the synthesized compounds have been established on the basis of elemental analysis and spectral data (IR, 1 H NMR, 13 C NMR, and mass spectrometry). Moreover, in order to investigate the mechanistic details of the reaction and to ascertain the regioselective outcome of the product, local nucleophilicity descriptors N k at B3LYP/6-311G++(d, p) level were determined and analyzed. KEYWORDS: Silica supported perchloric acid (HClO 4 ·SiO 2 ), benzoylation, oxazolo[4,5-b]pyridine, local nucleophilicity index.

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Section: Introductionmentioning

confidence: 99%

Acid-Catalyzed, Silica-Supported, One-Pot Benzoylation Route to Synthesize 2-(Substituted Phenyl)oxazolo[4,5-b]pyridines Under Ambient Conditions

Reen

Dudhe

Ahuja

et al. 2015

Synthetic Communications

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“…In continuation to the work performed by our group on benzoxazolinone and 2‐mercaptobenzoxazole‐based 1,2,3‐triazole conjugates as anti‐inflammatory compounds , we extended our studies to oxazolo[4,5‐b]pyridine‐2‐one moiety, the bio‐isostere of benzoxazolinone and 2‐mercaptobenzoxazole. Oxazolopyridinones have been reported to be pharmaceutically important as anti‐nociceptive, anti‐inflammatory, anti‐malarial, and Met kinase inhibitors . Recently, oxazolo‐pyridines have also been reported as potent GSK‐3 β inhibitors .…”

mentioning

confidence: 99%

Synthesis of Novel Oxazolo[4,5‐b]pyridine‐2‐one based 1,2,3‐triazoles as Glycogen Synthase Kinase‐3β Inhibitors with Anti‐inflammatory Potential

et al. 2016

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A novel series of oxazolo[4,5-b]pyridine-2-one based 1,2,3-triazoles has been synthesized by click chemistry approach and evaluated for in vitro GSK-3β inhibitory activity. Compound 4g showed maximum inhibition with IC50 value of 0.19 μm. Keeping in view the effect of GSK-3β inhibition on inflammation, compounds 4g, 4d, 4f, 4i, 4n and 4q exhibiting significant GSK-3β inhibition were examined for in vivo anti-inflammatory activity in rat paw edema model. The compounds 4g, 4d, 4f and 4i showed pronounced in vivo anti-inflammatory activity (76.36, 74.54, 72.72 and 70.90%, respectively, after 5h post-carrageenan administration) and were further found to inhibit the pro-inflammatory mediators, viz. NO, TNF-α, IL-1β, and IL-6 substantially in comparison with indomethacin, an anti-inflammatory drug as well as SB216763, a GSK-3β inhibitor, reported to exert a similar effect. Histopathology studies confirmed the tolerance of gastric mucosa to these compounds.

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ChemInform Abstract: Acylation of Oxazolo[4,5‐b]pyridin‐2(3H)‐ones, 2‐Phenyloxazolo[4,5‐b]pyridines and Pyrrolo[2,3‐b]pyridin‐2(2H)‐ones.

et al. 1997

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Acylation of Oxazolo [4,5-b]pyridin-2(3H)-ones, 2-Phenyloxazolo [4,5b]pyridines and Pyrrolo[2,3-b]pyridin-2(2H)-ones.-Several title compounds are acetylated and benzoylated using Pd-complexes as catalysts. The analgesic properties of the compounds are studied. Among these derivatives compound (X) possesses potent antinociceptive activity with moderate antiinflammatory properties. -(VIAUD, M.-C.; JAMONEAU, P.; BAUDIN, M.-L.; SAVELON, L.; GUILLAUMET, G.; Tetrahedron 53 (1997) 14, 5159-5168; Inst.

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Acylation of oxazolo[4,5-b]pyridin-2(3H)-ones, 2-phenyloxazolo[4,5-b]pyridines and pyrrolo[2,3-b]pyridin-2(2H)-ones

Cited by 18 publications

References 8 publications

Acid-Catalyzed, Silica-Supported, One-Pot Benzoylation Route to Synthesize 2-(Substituted Phenyl)oxazolo[4,5-b]pyridines Under Ambient Conditions

Acid-Catalyzed, Silica-Supported, One-Pot Benzoylation Route to Synthesize 2-(Substituted Phenyl)oxazolo[4,5-b]pyridines Under Ambient Conditions

Synthesis of Novel Oxazolo[4,5‐b]pyridine‐2‐one based 1,2,3‐triazoles as Glycogen Synthase Kinase‐3β Inhibitors with Anti‐inflammatory Potential

ChemInform Abstract: Acylation of Oxazolo[4,5‐b]pyridin‐2(3H)‐ones, 2‐Phenyloxazolo[4,5‐b]pyridines and Pyrrolo[2,3‐b]pyridin‐2(2H)‐ones.

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