Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents

Ertan, Tugba; Yildiz, İ̇lkay; Tekiner-Gülbaş, Betül; Bolelli, Kayhan; Temiz-Arpacı, Özlem; Özkan, Semiha Aydın; Kaynak, Fatma; Yalçın, İsmail; Aki, Esin

doi:10.1016/j.ejmech.2008.04.001

Cited by 91 publications

(40 citation statements)

References 33 publications

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“…Many substances containing this cyclic moiety were described in view of their wide range of biological activities. Ertan et al (2004) have synthesized a set of very active benzoxazoles against Bacillus subtilis, which also showed relevant antimicrobial activities against Escherichia coli and Candida albicans [5]. Potent benzoxazoles showing HIV reverse transcriptase inhibition were reported by Medebielle and colleagues and these products presented antifungal activities against Aspergillus niger and A. flavus [6].…”

Section: Introductionmentioning

confidence: 99%

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Carvalho

Alvarenga

Carmo

et al. 2017

Journal of Chemistry

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Eugenol is a natural allylphenol responsible for a wide range of biological activities, especially antimicrobial. Benzoxazoles are heterocycles with recognized antimicrobial activities. This paper describes the design, synthesis, and the biological results for benzoxazole type derivatives of eugenol as antifungal agents. The products were obtained in good yields by a four-step synthetic sequence involving aromatic nitration, nitroreduction, amide formation, and cycle condensation. They were evaluated against species of Candida spp. in microdilution assays, and four products (5a, 5b , 5c, and 5d ) were about five times more active than eugenol against C. albicans and C. glabrata. Two of them (5b and 5d ) showed good activity against C. krusei, a species which is naturally resistant to fluconazole. Furthermore, the active products were more selective than eugenol against human blood cells, showing that they are interesting substances for further optimization.

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Section: Introductionmentioning

confidence: 99%

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Carvalho

Alvarenga

Carmo

et al. 2017

Journal of Chemistry

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“…The synthesis of these totally 33 benzazole compounds were published before [15][16][17][18][19][20][21][22].…”

Section: Synthesis Of Compoundsmentioning

confidence: 99%

Inhibition of human glutathione transferase P1-1 by novel benzazole Derivatives

Musdal¹,

Ertan-Bolelli²,

Bolelli³

et al. 2012

Turk J Bioch

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“…Benzoxazoles are a class of heterocyclic compounds exhibiting therapeutical activities (Figure 2), such as, antifungal agents [38][39][40], cytotoxic compounds [41], as anti-inflammatory agents [42], as HIV-1 protease inhibitor [43], as an antibiotic [44], as CpIMPDH inhibitors [45], nonnucleoside HIV-1 reverse transcriptase inhibitors (NNRTI) [46], and antitumour agents [47].…”

Section: Benzoxazole Amides From Benzoylthioureasmentioning

confidence: 99%

Mechanistic Study on the Formation of Compounds from Thioureas

Laitonjam¹,

Nahakpam²

2018

Density Functional Calculations - Recent Progresses of Theory and Application

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Formation of 2-(N-arylamino)benzothiazole takes place, when N,N 0 -diphenylthioureas are treated with polymer-supported tribromide or with iodine-alumina as catalyst under solvent free conditions. However, when N-substituted-N 0 -benzoylthioureas are treated with polymer-supported tribromide or with iodine-alumina as catalyst either under various conditions or under solvent free conditions, decomposition takes place to give the respective benzamides and thiobenzamides. Mechanistic study of the formation of these compounds is studied using DFT calculations. It is found that electron donating group at the para-position of the aryl group of benzoylthiourea favors the formation of benzamide whereas the presence of electron withdrawing group at para-position of the aryl group of benzoylthiourea, formation of thiobenzamide takes place. When the catalyst is changed to diacetoxyiodobenzene (DIB) under similar reaction conditions, benzoxazole amides are formed; expected benzothiazoles or the decomposition products are not obtained. Mechanistic study of the reaction using DFT calculation again shows that the reaction followed through carbodiimide intermediate undergoes the formation of C-O bond in benzoxazole moiety, instead of the expected C-S bond formation of benzothiazole moiety via a sequential acylation and deacylation process.

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Synthesis, biological evaluation and 2D-QSAR analysis of benzoxazoles as antimicrobial agents

Cited by 91 publications

References 33 publications

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Antifungal Activity of New Eugenol-Benzoxazole Hybrids against Candida spp.

Inhibition of human glutathione transferase P1-1 by novel benzazole Derivatives

Mechanistic Study on the Formation of Compounds from Thioureas

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