Synthesis and microbiological activity of some novel 5-benzamido- and 5-phenylacetamido- substituted 2-phenylbenzoxazole derivatives

Şener, Esin; Arpacı, Özlem Temiz; Yalçın, İsmail; Altanlar, Nurten

doi:10.1016/s0014-827x(00)00059-8

Cited by 46 publications

(27 citation statements)

References 17 publications

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“…5-Amino-2-(p-substituted phenyl)benzoxazoles (1) were obtained by heating p-substituted benzoic acids with 2,4-diaminophenol in PPA (polyphosphoric acid) [31]. Amide compounds (2) were obtained from 5-amino-2-(p-substituted phenyl)benzoxazoles with chloroacetyl chloride [32Ϫ34].…”

Section: Resultsmentioning

confidence: 99%

“…The residue was boiled with 200 mg charcoal in ethanol and filtered. After the evaporation of the solvent in vacuo, the crude product was obtained and recrystallized [31].…”

Section: General Procedures For the Synthesis Of 5-amino-2-(p-substitumentioning

confidence: 99%

“…In our previous report, we described the preparation and in vitro antimicrobial activity of 2-[p-substituted phenyl]-5-[2-(substituted phenyl)acetamido]benzoxazole derivatives [31] as seen in Table 1. This time, the substitution, which is attached as acetamido moiety on the C-5 position of benzoxazole ring, has been changed to heterocyclic groups instead of phenyl for the antimicrobial effect.…”

Section: Introductionmentioning

confidence: 99%

“…Therefore, a series of novel 5-[2-(morpholin-4-yl)acetamido] and/or 5-[2- phenyl]benzoxazole derivatives 3Ϫ14 (Figure 4) has been synthesized as the target compounds in order to examine their microbiological activitiy against various Gram-positive and Gram-negative bacteria and the different yeasts in comparison with several control drugs because in the need of new and different antibacterial agents that are resistant to inactivation by bacterial enzymes. Their structure-activity relationships (SAR) were also studied by using either newly or previously synthesized compounds [31] and the structures of the newly synthesized compounds are supported by spectral data ( Table 2). …”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antimicrobial Activity of Some 5‐[2‐(Morpholin‐4‐yl)acetamido] and/or 5‐[2‐(4‐Substituted piperazin‐1‐yl)acetamido]‐2‐(p‐substituted phenyl)benzoxazoles

Temiz-Arpacı

Özdemir

Yalçın

et al. 2005

Archiv der Pharmazie

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In this study, a series of twelve novel 5-[2-(morpholin-4-yl)acetamido] and/or 5-[2-(4-substituted pip-erazine-1-yl)acetamido]-2-(p-substituted phenyl]benzoxazole derivatives have been synthesized and their structures were confirmed by IR, (1)H NMR, and mass spectral data. These compounds were prepared by reacting 5-(2-chloroacetamido)-2-(4-p-substituted-phenyl)benzoxazoles, which were obtained by using 5-amino-2-[p-substituted-phenyl]benzoxazoles with chloroacetyl chloride, in the presence of morpholine or 1-substituted piperazines. All synthesized compounds 3-14 were tested by using the method of twofold serial dilution technique for in vitro activities against certain strains of Gram-positive, Gram-negative bacteria as well as the yeasts Candida albicans, Candida krusei, and Candida glabrata in comparison with standard drugs. Microbiological results showed that the newly synthesized compounds possessed a broad spectrum of activity, showing MIC values of 3.12-50 mug/mL against the Candida species.

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Section: Resultsmentioning

confidence: 99%

“…The residue was boiled with 200 mg charcoal in ethanol and filtered. After the evaporation of the solvent in vacuo, the crude product was obtained and recrystallized [31].…”

Section: General Procedures For the Synthesis Of 5-amino-2-(p-substitumentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Antimicrobial Activity of Some 5‐[2‐(Morpholin‐4‐yl)acetamido] and/or 5‐[2‐(4‐Substituted piperazin‐1‐yl)acetamido]‐2‐(p‐substituted phenyl)benzoxazoles

Temiz-Arpacı

Özdemir

Yalçın

et al. 2005

Archiv der Pharmazie

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“…Several derivatives shows broad range of biological activity, i.e., antibacterial, analgesic, virucidal, plant growth regulator, etc. They are used as important intermediates in the syntheses of their benzamido, phenylacetamido, phenyl benzoxazole derivatives and amino acid esters [1][2][3][4][5][6].…”

Section: Introductionmentioning

confidence: 99%

Structural, analytical and DSC references to resolution of 2-methoxy-2-phenylacetic acid with chiral 1-cyclohexylethylamines through gas-antisolvent precipitation

et al. 2017

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Synthesis and Antimicrobial Activity of New 2‐[p‐Substituted‐benzyl]‐5‐[substituted‐carbonylamino]benzoxazoles

Yildiz

Tekiner-Gülbaş

Yalçın

et al. 2004

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A series of 23 new 2-[p-substituted-benzyl]-5-[p-substituted-phenyl/benzyl-carbonylamino]benzoxazole derivatives has been synthesized by reacting 5-amino-2-[p-substituted-benzyl]benzoxazoles with the appropriate carboxylic acid chlorides. The structures of the synthesized compounds were confirmed by IR and (1)H-NMR spectral data. Antimicrobial activities of the compounds were investigated using the twofold serial dilution technique against two gram-positive and two gram-negative bacteria and three Candida species in comparison with standard drugs. Microbiological results indicated that the newly synthesized 2-[p-substituted-benzyl]-5-[p-substituted-phenyl/benzyl-carbonylamino]benzoxazole derivatives (3-25) possessed a broad spectrum of activity, showing MIC values of 6.25-200 microg/mL against the gram-positive and gram-negative microorganisms tested. Moreover, they showed significant antifungal activity with MIC values of 3.12-100 microg/mL against the Candida species tested. Especially, with a MIC value of 3.12 microg/mL, 2-benzyl-5-[p-bromobenzyl-carbonylamino]benzoxazole 9 displayed the same activity against C. glabrata as the standard drug myconazol.

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Synthesis and microbiological activity of some novel 5-benzamido- and 5-phenylacetamido- substituted 2-phenylbenzoxazole derivatives

Cited by 46 publications

References 17 publications

Synthesis and Antimicrobial Activity of Some 5‐[2‐(Morpholin‐4‐yl)acetamido] and/or 5‐[2‐(4‐Substituted piperazin‐1‐yl)acetamido]‐2‐(p‐substituted phenyl)benzoxazoles

Synthesis and Antimicrobial Activity of Some 5‐[2‐(Morpholin‐4‐yl)acetamido] and/or 5‐[2‐(4‐Substituted piperazin‐1‐yl)acetamido]‐2‐(p‐substituted phenyl)benzoxazoles

Structural, analytical and DSC references to resolution of 2-methoxy-2-phenylacetic acid with chiral 1-cyclohexylethylamines through gas-antisolvent precipitation

Synthesis and Antimicrobial Activity of New 2‐[p‐Substituted‐benzyl]‐5‐[substituted‐carbonylamino]benzoxazoles

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