Sequential addition of 2-potassio-2-nitropropane and oxygen to 4-arylidene-oxazol-5-ones: a new method for 2-aryl butenoic acid imides

Lalitha, N.; Bhalerao, U. T.; Iyengar, D. S.

doi:10.1039/c39910000897

Cited by 3 publications

(5 citation statements)

References 6 publications

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“…The white formed precipitate was collected by filtration and washed out with water (negative reaction for chloride). The spectral data was in agreement with literature data [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ].…”

Section: Methodssupporting

confidence: 90%

“…Also, the configuration of the ring opened products is the same as that of the parent oxazolone [ 32 ]. Compounds 2a , 2c , 2d , 2e , 2f , 3a , 6c have been synthesized previously under different experimental conditions [ 33 , 34 , 35 , 36 , 37 , 38 , 39 , 40 , 41 , 42 , 43 , 44 ]. The structures of the new compounds were confirmed by IR, 1 H-NMR, MS (ΕSI) and elemental analysis and they were found to be consistent with the proposed structures.…”

Section: Resultsmentioning

confidence: 99%

“…(Z)-4-(4-Phenoxybenzylidene)-2-phenyloxazol-5(4H)-one ( 2f ) [ 43 , 44 ]. Yield: 12%; R f = 0.9 (CH 3 COOC 2 H 5– petroleum ether, 3:7); m.p.…”

Section: Methodsmentioning

confidence: 99%

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5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

et al. 2020

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The five membered heterocyclic oxazole group plays an important role in drug discovery. Oxazolones present a wide range of biological activities. In this article the synthesis of 4-substituted-2-phenyloxazol-5(4H)-ones from the appropriate substituted aldehydes via an Erlenmeyer–Plochl reaction is reported. Subsequently, the corresponding benzamides were produced via a nucleophilic attack of a secondary amine on the oxazolone ring applying microwave irradiation. The compounds are obtained in good yields up to 94% and their structures were confirmed using IR, 1H-NMR, 13C-NMR and LC/MS data. The in vitro anti-lipid peroxidation activity and inhibitory activity against lipoxygenase and trypsin induced proteolysis of the novel derivatives were studied. Inhibition of carrageenin-induced paw edema (CPE) and nociception was also determined for compounds 4a and 4c. Oxazolones 2a and 2c strongly inhibit lipid peroxidation, followed by oxazolones 2b and 2d with an average inhibition of 86.5%. The most potent lipoxygenase inhibitor was the bisbenzamide derivative 4c, with IC50 41 μM. The benzamides 3c, 4a–4e and 5c were strong inhibitors of proteolysis. The replacement of the thienyl moiety by a phenyl group does not favor the protection. Compound 4c inhibited nociception higher than 4a. The replacement of thienyl groups by phenyl ring led to reduced biological activity. Docking studies of the most potent LOX inhibitor highlight interactions through allosteric mechanism. All the potent derivatives present good oral bioavailability.

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Section: Methodssupporting

confidence: 90%

Section: Resultsmentioning

confidence: 99%

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5-(4H)-Oxazolones and Their Benzamides as Potential Bioactive Small Molecules

et al. 2020

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“…Potassium salt of 2-nitropropane reacts with 4-arylideneoxazol-5-ones 192 in the presence of molecular oxygen to afford 2-arylbutenoic acid imides 193 (Scheme ) . The addition product 194 initially formed is believed to react with oxygen, giving a hydroperoxide intermediate 195 that decomposes with loss of CO 2 and HNO 2 to the final product 193 .…”

Section: Conjugate Addition−elimination Reactionsmentioning

confidence: 99%

“…Regiochemical troubles can be avoided or minimized using 1,2-disubstituted alkenes bearing com- 147 The addition product 194 initially formed is believed to react with oxygen, giving a hydroperoxide intermediate 195 that decomposes with loss of CO 2 and HNO 2 to the final product 193. An endoperoxide arising from a cycloaddition reaction between 194 and oxygen is also a possible intermediate in this process.…”

Section: Conjugate Addition−elimination Reactionsmentioning

confidence: 99%