Synthesis of new isoxazoles and dihydroisoxazoles and in vitro evaluation of their antifungal activity

Chevreuil, Francis; Landreau, Anne; Séraphin, Denis; Larcher, Gérald; Bouchara, Jean‐Philippe; Richomme, Pascal

doi:10.1080/14756360701425279

Cited by 11 publications

(4 citation statements)

References 18 publications

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“…This nucleus is present in antifungal compounds, such as micafungin 7 and azoles derivatives 8 (Figure ) . The presence of the isoxazole nucleus increased the potency of micafungin 7 ten times compared to the natural echinocandin .…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

Trefzger

Barbosa

Scapolatempo

et al. 2019

Archiv der Pharmazie

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Nineteen 3,5-disubstituted-isoxazole analogs were synthesized based on nitrofuran scaffolds, by a [3 + 2] cycloaddition reaction between terminal acetylenes and 5-nitrofuran chloro-oxime. The compounds were obtained in moderate to very good yields (45-91%). The antileishmanial activity was assayed against the promastigote and amastigote forms of Leishmania (Leishmania) amazonensis. Alkylchlorinated compounds 14p-r were active on both the promastigote and amastigote forms, with emphasis on compound 14p, which showed strong activity against the amastigote form (IC 50 = 0.6 μM and selectivity index [SI] = 5.2). In the alkyl series, compound 14o stands out with an IC 50 = 8.5 μM and SI = 8.0 on the amastigote form. In the aromatic series, the most active compounds were those containing electron-donor groups, such as trimethoxy isoxazole 14g (IC 50 = 1.2 μM and SI = 20.2); compound 14h, with IC 50 = 7.0 μM and SI = 6.1; and compound 14j containing the 4-SCH 3 group, with IC 50 = 5.7 μM and SI = 10.2. In addition, the antifungal activity of 19 nitrofuran isoxazoles was evaluated against five strains of Candida (C. albicans, C. parapsilosis, C. krusei, C. tropicalis, and C. glabrata). Eleven isoxazole derivatives were active against C. parapsilosis, and compound 14o was found to be the most active (minimal inhibitory concentration [MIC] = 3.4 μM) for this strain. Compound 14p was active against all the strains tested, with an MIC = 17.5 μM for C. glabrata, lower than that of the fluconazole used as the reference drug. K E Y W O R D S5-nitrofuran scaffolds, antifungal activity, antileishmanial activity, drug design, isoxazole core *Ozildéia S. Trefzger, Natália V. Barbosa, and Renata L. Scapolatempo contributed equally to this work.

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Section: Introductionmentioning

confidence: 99%

“…The presence of the isoxazole nucleus increased the potency of micafungin 7 ten times compared to the natural echinocandin . The azole derivative with isoxazole nucleus 8 showed activity (minimal inhibitory concentration [MIC] = 2 µg/ml) against fluconazole and voriconazole‐resistant C. glabrata strains …”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

Trefzger

Barbosa

Scapolatempo

et al. 2019

Archiv der Pharmazie

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“…These pyrazole and isoxazoles were prepared from chalcones which are important intermediate products and they also possess biological and pharmacological applications (Dhar, 1981). The substituted azole unit is an essential pharmacophore of number of antifungal (Chevreuil et al, 2007), antibacterial (Solanki and wadodkar, 2003) and various biological activities (Gautam, 2013;Patel, 2017;Dongre, 2017;Ali, 2011) Therefore considering the antifungal and antibacterial potential of azole derivatives (Sharma and Sharma, 2010), we would like to report herein the synthesis of new isoxazolines and evaluation of their antibacterial activity against (Gram-ve) and E-coli,S. typhi P. aeruginosa, S. aureus ( Gram +ve) bacterial strain by using disc diffusion method ( Shinde et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of some chloro-substituted isoxazoline derivatives as antibacterial agents

Deshmukh¹,

Kottapalle²,

Shinde³

2018

Asian J Pharm Pharmacol

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Objectives: The chemistry of chalcones has generated intensive scientific studies throughout the world. Especially interest has been focused on the synthesis and biodynamic activities of isoxazoline derivatives. In recent year numerous isoxazoline derivatives have been synthesized for their anticancer, anti-inflammatory, cytotoxic, antiviral activities. The reaction of substituted chalcones with hydroxylamine hydrochloride in presence of acetic acid gave isoxazoline derivatives. : The five membered oxygen and Nitrogen containing compounds exhibited Material and methods antioxidant, analgesic, antibacterial, antifungal activities. Therefore the attempt have been made to synthesize chlorosubstituted isoxazolines by the reaction of different substituted chalcones with hydroxylamine hydrochloride in presence of few drops of acetic acid. All the synthesized compounds confirmed by TLC and spectral analysis and also screened for their antibacterial activity. : The novel chloro-substituted isoxazolines showed good to moderate Results antibacterial activity against Gram+ve and Gram-ve bacterial strains tested. : These compounds Conclusion containing chloro, bromo, iodo groups were found showed potent antibacterial, antifungal activities. These findings promoted us to to synthesize novel chloro-substituted isoxazolines derivatives which are found to be potential antibacterial agents.

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“…However, the extensive use of azole compounds has given rise to the emergence of azole-resistant isolates in pathogenic yeasts which are often associated to an increased activity of the efflux pump [6]. Despite recent developements, there is still a need for a genuinely broad-spectrum and low toxicity antifungal azole agents capable to overcome this increased efflux [7,8] Considering this need, we recently reported the synthesis of new 2-aryl-1-azolyl-3-thienylbutan-2-ols [9], isoxazoles and isoxazolines [10] which kept a high activity against a Candida glabrata azole-resistant strain which overexpressed genes coding for the efflux pump proteins. [6] These studies pointed out the utility of a five-membered heteroaromatic ring in the conazole side-chain for the escaping of the efflux pumps.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of new 1-[2-Azido-2-(2,4-dichlorophenyl)ethyl]-1H/-imidazoles andin vitroevaluation of their antifungal activity

Chevreuil¹,

Landreau²,

Séraphin³

et al. 2008

Journal of Enzyme Inhibition and Medicinal Chemistry

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Synthesis of new isoxazoles and dihydroisoxazoles and in vitro evaluation of their antifungal activity

Cited by 11 publications

References 18 publications

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

Design, synthesis, antileishmanial, and antifungal biological evaluation of novel 3,5‐disubstituted isoxazole compounds based on 5‐nitrofuran scaffolds

Synthesis of some chloro-substituted isoxazoline derivatives as antibacterial agents

Synthesis of new 1-[2-Azido-2-(2,4-dichlorophenyl)ethyl]-1H/-imidazoles andin vitroevaluation of their antifungal activity

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