Synthesis and Chymotrypsin Inhibitory Activity of Substituted Oxazolones

Abstract

A variety of oxazolones (3-18) with structural variation at C-2 and C-4 were synthesized and evaluated as chymotrypsin inhibitors. The synthesized compounds showed varying degree of chymotrypsin inhibitory activity ranging IC 50 values from 12.62 ± 1.32 -126.57 ± 1.06 μM, if compared to standard chymostatin (IC 50 = 7.01 ± 0.1 μM). Compounds 3,9,10,13,14, and 15 have IC 50 values 17.03 ± 0.78, 69.05 ± 1.48, 12.62 ± 1.32, 17.29 ± 0.93, 126.57 ± 1.06, and 31.55 ± 1.31 μM, respectively. This study reveals that the substitution of functional group (s) at C-2 and C-4 positions plays a vital role in the activity of this series of compounds. The size and electron donating or withdrawing effects of substituents influenced the activity.

Synthesis and leishmanicidal activity of 2,3,4-substituted-5-imidazolones

“…Chemistry Imidazolones 1-29 were synthesized from differently substituted E-oxazolones [21][22][23] (1 mmol) and substituted aromatic amines (1.1 mmol) in anhydrous pyridine through microwave irradiation (Scheme 1). The structures of imidazolones 1-29 were determined using different spectroscopic techniques, including 1 H-NMR, EI, IR, and UV, and by elemental analysis.…”

“…General procedure for the synthesis of compounds 1-29 A mixture of differently substituted E-oxazolones [22][23][24] (1 mmol) and substituted aromatic amines (1.1 mmol) in anhydrous pyridine were irradiated by microwaves (CEM Discover system, model 908010) for 10-15 min at 150°C. The input power of the microwave reactor was 300 W, and the same power was used for all reactions.…”

“…In our ongoing research on leishmaniasis [17][18][19][20] , we synthesized 29 imidazolones, 1-29, by treating different oxazolones with varyingly substituted aromatic amines. In a typical reaction, a mixture of differently substituted E-oxazolones [21][22][23] (1 mmol) and substituted aromatic amines (1.1 mmol) in anhydrous pyridine were irradiated by microwaves to afford compounds 1-29. Compounds 1-29 were randomly screened for their in vitro anti-leishmanial potential.…”

Spectroscopic, Structural and Density Functional Theory (DFT) Studies of Two Oxazol-5-one Derivatives

“…[1][2][3][4][5] Due to the five -membered heterocyclic core, oxazol-5-ones are biologically active molecules and widely used in biomedicinal applications. [6][7][8][9] Oxazol-5-ones have found important roles as drugs, enzyme inhibitors and fluorescent sensors. [7][8][9][10] Oxazol-5-ones are also used in dye industry owing to the fact that oxazol-5-ones are easily obtainable in crystalline states and they possess promising photochemical/photophysical properties due to their chromophore group.…”

“…[6][7][8][9] Oxazol-5-ones have found important roles as drugs, enzyme inhibitors and fluorescent sensors. [7][8][9][10] Oxazol-5-ones are also used in dye industry owing to the fact that oxazol-5-ones are easily obtainable in crystalline states and they possess promising photochemical/photophysical properties due to their chromophore group. 10,11 Herein, we report on the synthesis, spectral characterization and theoretical studies of two oxazol-5-one derivatives.…”