Synthesis of 2,3 and 4,5-Dihydro-hydroxy-isoxazoles and Isoxazoles Under Different pH Conditions

Andrzejak, Virginie; Millet, Régis; Bakali, Jamal El; Abdelhalim, Mohamed Anwar K; Gluszok, Sébastien; Chavatte, Philippe; Bonte, Jean‐Paul; Vaccher, Claude; Lipka, Emmanuelle

doi:10.2174/157017810790533922

Cited by 11 publications

(2 citation statements)

References 17 publications

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“…The synthesis of 5-substituted isoxazole acids was carried out using known synthetic methods [21] by the reaction of commercially available ketones with diethyl oxalate in the presence of sodium ethoxide [22]. The synthetic route included cyclization of ethyl 2,4-dioxobutanoates into ethyl isoxazole-3-carboxylates by the addition of hydroxylamine hydrochloride in ethanol at reflux [23] followed by saponification of the ester function with sodium hydroxide in ethanol. Corresponding acyl chlorides 3a-g were synthesized in the reaction of the isoxazole acids and thionyl chloride in benzene and used without purification in acylation of adenine (1) or 8-aminoquinoline (2) (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

5-Substituted N-(9H-purin-6-yl)-1,2-oxazole-3-carboxamides as xanthine oxidase inhibitors

et al. 2020

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Synthetic 6-substituted purine derivatives are known to exhibit diverse bioactivity. In this paper, a series of N-(9H-purin-6-yl)-1,2-oxazole-3-carboxamide derivatives were synthesized and evaluated in vitro against xanthine oxidase, an enzyme of purine catabolism. The introduction of aryl substituent at position 5 of the oxazole ring was found to increase the inhibition efficiency. Some of the inhibitors containing 5-substituted isoxazole and purine moieties were characterized by IC50 values in the nanomolar range. According to the kinetic data, the most active N-(9H-purin-6-yl)-5-(5,6,7,8-tetrahydronaphthalen-2-yl)-1,2-oxazole-3-carboxamide demonstrated a competitive type of inhibition with respect to the enzyme-substrate. Molecular docking was carried out to elucidate the mechanism of enzyme-inhibitor complex formation. The data obtained indicate that xanthine oxidase may be one of the possible targets for the bioactive purine carboxamides.

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Section: Resultsmentioning

confidence: 99%

5-Substituted N-(9H-purin-6-yl)-1,2-oxazole-3-carboxamides as xanthine oxidase inhibitors

et al. 2020

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“…Acid conditions gave 3,5-isoxazole esters (Route a,Fig. 5) principally whereas reactions under neutral and basic conditions led to different 4,5 and 2,3-dihydro-hydroxy-isoxazoles, respectively(Andrzejak et al 2010). Heating of 2-formyl azirines for 24 h in toluene at 200°C (Route b,Fig.…”

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confidence: 98%

The synthetic and therapeutic expedition of isoxazole and its analogs

2018

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Isoxazole, constituting an important family of five-membered heterocycles with one oxygen atom and one nitrogen atom at adjacent positions is of immense importance because of its wide spectrum of biological activities and therapeutic potential. It is, therefore, of prime importance that the development of new synthetic strategies and designing of new isoxazole derivatives should be based on the most recent knowledge emerging from the latest research. This review is an endeavor to highlight the progress in the chemistry and biological activity of isoxazole derivatives which could provide a low-height flying bird's eye view of isoxazole derivatives to the medicinal chemists for the development of clinically viable drugs using this information.

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ChemInform Abstract: Synthesis of 2,3 and 4,5‐Dihydro‐hydroxy‐isoxazoles and Isoxazoles under Different pH Conditions.

et al. 2010

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Synthesis of 2,3 and 4,5-Dihydro-hydroxy-isoxazoles and Isoxazoles Under Different pH Conditions

Cited by 11 publications

References 17 publications

5-Substituted N-(9H-purin-6-yl)-1,2-oxazole-3-carboxamides as xanthine oxidase inhibitors

5-Substituted N-(9H-purin-6-yl)-1,2-oxazole-3-carboxamides as xanthine oxidase inhibitors

The synthetic and therapeutic expedition of isoxazole and its analogs

ChemInform Abstract: Synthesis of 2,3 and 4,5‐Dihydro‐hydroxy‐isoxazoles and Isoxazoles under Different pH Conditions.

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