Synthesis and antiinflammatory activity of some 2-heteroaryl-.alpha.-methyl-5-benzoxazoleacetic acids

Dunwell, D. W.; Evans, D. E.; Hicks, T. A.

doi:10.1021/jm00245a026

Cited by 29 publications

(16 citation statements)

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“…The aminobenzoxazole 1 is an analogue of benoxaprofen and flunoxaprofen, which are known NSAIDs with anti-inflammatory properties 23,24. In fact, benoxaprofen has been shown to promote accelerated healing in a rat UC model of inflammatory bowel disease, which could be explained by its action in leukotriene B4 inhibition 30.…”

Section: Discussionmentioning

confidence: 99%

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Synthesis and evaluation of mutual azo prodrug of 5-aminosalicylic acid linked to 2-phenylbenzoxazole-2-yl-5-acetic acid in ulcerative colitis

Jilani¹,

Shomaf²,

Alzoubi³

2013

DDDT

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In this study, the syntheses of 4-aminophenylbenzoxazol-2-yl-5-acetic acid, (an analogue of a known nonsteroidal anti-inflammatory drug [NSAID]) and 5-[4-(benzoxazol-2-yl-5-acetic acid)phenylazo]-2-hydroxybenzoic acid (a novel mutual azo prodrug of 5-aminosalicylic acid [5-ASA]) are reported. The structures of the synthesized compounds were confirmed using infrared (IR), hydrogen-1 nuclear magnetic resonance (1H NMR), and mass spectrometry (MS) spectroscopy. Incubation of the azo compound with rat cecal contents demonstrated the susceptibility of the prepared azo prodrug to bacterial azoreductase enzyme. The azo compound and the 4-aminophenylbenzoxazol-2-yl-5-acetic acid were evaluated for inflammatory bowel diseases, in trinitrobenzenesulfonic acid (TNB)-induced colitis in rats. The synthesized diazo compound and the 4-aminophenylbenzoxazol-2-yl-5-acetic acid were found to be as effective as 5-aminosalicylic acid for ulcerative colitis. The results of this work suggest that the 4-aminophenylbenzoxazol-2-yl-5-acetic acid may represent a new lead for treatment of ulcerative colitis.

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Section: Discussionmentioning

confidence: 99%

“…They belong to the class of benzoxazoleacetic acid derivatives 23,24. Benoxaprofen has been recognized to be an NSAID with a spectrum of activity that is different from other NSAIDs.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluation of mutual azo prodrug of 5-aminosalicylic acid linked to 2-phenylbenzoxazole-2-yl-5-acetic acid in ulcerative colitis

Jilani¹,

Shomaf²,

Alzoubi³

2013

DDDT

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“…Inspired by the nature, researches synthesized a variety of benzoxazole derivatives and screened for their biological activity which resulted in several marketed drugs (Figure ) …”

Section: Introductionmentioning

confidence: 99%

Benzoxazole Derivatives as Promising Antitubercular Agents

Šlachtová

Brulíková

2018

ChemistrySelect

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Tuberculosis (TB) is an infectious disease caused predominantly by bacillus Mycobacterium tuberculosis (MTB). The increasing prevalence of multidrug‐resistant MTB necessitates the discovery and development of alternative drugs against tuberculosis with a new mechanism of action. Over the past years, several benzoxazole derivatives have been synthesized and screened for their biological activity. Interestingly, some of them had promising antitubercular activity. Despite that, none of the benzoxazole derivatives has entered the phase of the preclinical hit‐to‐lead optimization step in anti‐TB research. In this review, we are summarizing recently published articles that evaluate the potency of benzoxazole heterocycle in the development of novel anti‐TB agents and outlined the future aspects of this promising heterocycle.

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“…Particularly, 2-substituted benzoxazole derivatives have remarkable biological potential including anticancer, antitumour and inhibitory activities. [2][3][4][5][6][7] Furthermore, this motif is also abundant in several functional materials such as engineering plastics, optical brightener for textiles and metal sensors. [8][9][10][11][12][13][14][15][16] As a result, there are increasing demands to devise versatile methods for the construction of 2-substituted benzoxazoles.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of 2-Aryl Benzoxazoles from Aldoximes

Panda¹

2017

MOJBOC

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Wide spectrum of biological activities of benzoxazole heterocycles aroused great interest for the development of newer methods for their synthesis. We herein report a copper catalyzed method for the synthesis of 2-aryl benzoxazoles from the reaction of aldoxime and 2-iodobromobenzene using N,N'-dimethyl ethylenediamine (DMEDA) as the ligand. The reaction proceeds with the copper-catalyzed dehydration of aldoxime leading to the nitilium ion which might be undergoing hydrolysis and subsequent C-O bond formation in one-pot to afford 2-aryl benzoxazoles. The pure products were isolated and characterized by 1 H NMR, and 13 C NMR data.

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Synthesis and antiinflammatory activity of some 2-heteroaryl-.alpha.-methyl-5-benzoxazoleacetic acids

Abstract: The syntheses of eight of the title compounds are described. The compounds possessed activity comparable with that of the previously tested 2-substituted phenyl analogs in the carrageenan-induced rat paw edema test.

Cited by 29 publications

References 0 publications

Synthesis and evaluation of mutual azo prodrug of 5-aminosalicylic acid linked to 2-phenylbenzoxazole-2-yl-5-acetic acid in ulcerative colitis

Synthesis and evaluation of mutual azo prodrug of 5-aminosalicylic acid linked to 2-phenylbenzoxazole-2-yl-5-acetic acid in ulcerative colitis

Benzoxazole Derivatives as Promising Antitubercular Agents

Synthesis of 2-Aryl Benzoxazoles from Aldoximes

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