2-(Substituted phenyl)oxazolo[4,5-b]pyridines and 2-(substituted phenyl)oxazolo[5,4-b]pyridines as nonacidic antiinflammatory agents

Clark, Robert L.; Pessolano, A. A.; Witzel, B. E.; Lanza, Thomas J.; Shen, T. Y.; Arman, C. G. Van; Risley, Edwin A.

doi:10.1021/jm00209a014

Cited by 59 publications

(13 citation statements)

References 3 publications

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“…The adducts have been used for preparation of heterocyclic compounds, 4,5,37,46--48,52-54,56,59,63 in Beckmann rearrangement,43 for cyclizations, 4,5,38,40,44,45,57,62,64,66,68 (a review covering cyclizations under Vilsmeier-Haack conditions is available 77 ), for preparation of amidines, 5,7,39,41,42,55,76 in von Braun degradation,61 in rearrangements,68 in condensation reactions,69 in substitution of aromatic compounds,4,6,7,71,74 in reduction of amides,72 in amide dimerization 73 and for preparation of isonitriles. 5 The adduct from DMF and POBr3 was used for similar purposes.…”

Section: Synthesis Oflminium Salts Orthoesters and Related Compoundsmentioning

confidence: 99%

Synthesis of Iminium Salts, Orthoesters and Related Compounds

Kantlehner

1991

Comprehensive Organic Synthesis

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Section: Synthesis Oflminium Salts Orthoesters and Related Compoundsmentioning

confidence: 99%

Synthesis of Iminium Salts, Orthoesters and Related Compounds

Kantlehner

1991

Comprehensive Organic Synthesis

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“…Benzoxazole derivative, 1,3‐benzoxazole‐4‐carbonitirle, acts as a support for β‐1,6‐glucan synthesis inhibitors with potent antifungal activity against candida species (Kuroyanagi et al ., ). Oxazole derivatives are used as anti‐inflammatories, analgesics, anti‐pyretics, and antagonists (Clark et al ., ; Barni et al ., ). 2‐(4′‐ N , N ‐dimethylaminophenyl)imidazo[4,5‐b]pyridine (DMAPIP‐b) and some other pyridoimidazole derivatives act as inhibitor for aurora kinases (Bavetsias et al ., ).…”

Section: Introductionmentioning

confidence: 99%

Interactions of a few azole derivatives with a transport protein: role of heteroatoms

Mishra

Malakar

Biswal

et al. 2015

J of Molecular Recognition

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The interaction of a few azole derivatives, 2-(4'-N,N-dimethylaminophenyl)benzimidazole, 2-(4'-N,N-dimethylaminophenyl)benzoxazole, 2-(4'-N,N-dimethylaminophenyl)oxazolo[4,5-b]pyridine with bovine serum albumin (BSA) were examined by absorption and fluorescence spectroscopy. The results were compared with the previously studied imidazopyridine derivative 2-(4'-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine. Displacement studies were carried out with site selective probes to locate the binding site of these ligands. The spectral shifts and the binding constant vary depending on the nature of the ligand. The fluorescence intensity of both oxazole derivatives 2-(4'-N,N-dimethylaminophenyl)benzoxazole and 2-(4'-N,N-dimethylaminophenyl) oxazolo[4,5-b]pyridine increases substantially in the presence of BSA, whereas the intensity of 2-(4'-N,N-dimethylaminophenyl)benzimidazole decreases. However, hypsochromic shift is observed in presence of BSA. The results obtained from the docking studies are also in good agreement with the experimental results. The location and orientation of binding depend upon the nature of the ligand. The studies revealed that apart from hydrophobic interaction, hydrogen bonding also plays a vital role in the molecular binding. Oxazoles have higher binding affinity than imidazoles and substitution of extra nitrogen further increases the binding affinity.

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“…In particular, 2-(phenyl)oxazolo [4,5-b]pyridine derivatives have been traditionally synthesized by condensation of 2-amino-3-hydroxypyridine with benzoic acid derivatives, [9] benzoic anhydride, [10] benzoyl chloride, [11] orthoesters [12] and also by direct arylation of oxazolo [4,5-b]pyridine. [13] Several catalysts have been reported in the literature for the synthesis of this moiety viz., polyphosphoric acid, trimethyl sillyl polyphosphate and silica supported sulphuric acid .…”

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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2-(Substituted phenyl)oxazolo[4,5-b]pyridines and 2-(substituted phenyl)oxazolo[5,4-b]pyridines as nonacidic antiinflammatory agents

Cited by 59 publications

References 3 publications

Synthesis of Iminium Salts, Orthoesters and Related Compounds

Synthesis of Iminium Salts, Orthoesters and Related Compounds

Interactions of a few azole derivatives with a transport protein: role of heteroatoms

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

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