Click chemistry inspired structural modification of azole antifungal agents to synthesize novel ‘drug like’ molecules

Pericherla, Kasiviswanadharaju; Khedar, Poonam; Khungar, Bharti; Kumar, Anil

doi:10.1016/j.tetlet.2012.09.129

Cited by 30 publications

(16 citation statements)

References 24 publications

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“…21 Previously, it was shown that "click" synthesis of 1,4-disubstituted 1,2,3-triazoles proceeded in good yields using CuSO 4 + NaAsc in PEG 400/water under mild conditions for a short time, due to very efficient activation by PEG 400. [22][23][24][25] However this effect is not observed in the present study, because similar yields were obtained when compared between A and B under different catalysts loading. It appears that the concentration of PEG played a key role in the previous studies (PEG 400/water = 1:1, v:v).…”

Section: Introductioncontrasting

confidence: 56%

“…It appears that the concentration of PEG played a key role in the previous studies (PEG 400/water = 1:1, v:v). [22][23][24][25] Here the present PEG concentration is too low to provide such an effect, and therefore the PEG ligand does not lead to a good yield. When the monofunctional 1,2,3-triazole terminated with PEG 2000 (PEG-mono-trz-Cu I , 1 equiv., C), 26 was introduced the yields increased, especially that under low catalyst amounts (i.e.…”

Section: Introductionmentioning

confidence: 88%

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Design and Applications of an Efficient Amphiphilic “Click” Cu^I Catalyst in Water

Wang

et al. 2016

ACS Catal.

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The copper(I)-catalyzed azide alkyne cycloaddition (CuAAC) using the conventional Sharpless-Fokin catalyst that consists of CuSO 4 + Na ascorbate, the most well-known and used "click" reaction, is considerably accelerated by the addition of a tris(triazolyl)-polyethylene glycol (tris-trz-PEG) amphiphilic ligand in water under ambient conditions. Only parts-per-million Cu I were necessary to reach quantitative yields with TON up to 86000 and TOF 3600 h -1 . The ligand was fully recycled, and the catalyst reused at least 6 times without decomposition. Large-scale syntheses were also successfully achieved with 93 % yield. The catalyst was applied to the efficient synthesis of various useful functional products with medicinal, catalytic, targeting, and labeling properties.

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Section: Introductioncontrasting

confidence: 56%

Section: Introductionmentioning

confidence: 88%

Design and Applications of an Efficient Amphiphilic “Click” Cu^I Catalyst in Water

Wang

et al. 2016

ACS Catal.

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“…[9] On the other hand, the modification of the structures of biologically active compounds by means of hydrogen atom substitution by fluorine atom(s) or fluorinated group(s) often leads to an increase in their biological activity and selectivity. [10] These huge successes of fluorinated-containing bioactive compounds continue to stimulate research on fluorine in several areas for drug discovery. For instance, the fungicides developed by Minoru et al, which contain the ptrifluoromethylphenyl moiety, were studied as antifungal agents on mamals [10].…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of novel fungicides for the management of Fusarium DieBack disease

et al. 2019

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Abstract. Fusarium Dieback, a new and lethal insect-vectored disease can host over 300 tree species including the avocado trees. This problem has recently attracted the attention of synthetic chemist not only to develop new triazol antifungal agents but also due to severe drug resistance to “classic” triazol antifungal agents. Here, a series of novel antifungal triazoles with a p-trifluoromethylphenyl moiety were synthesized and characterized by spectroscopic and spectrometric methods. Most of the target compounds synthesized showed from modest to good inhibitory activity and less phytotoxicity in comparison with the commercially available propiconazol; in particular, compounds 7 and 13 were active against both Fusarium solani and Fusarium euwallaceae. The results showed that compounds 7, 13, and 4 have great potential to be developed as new antifungal agents because of both good antifungal activity and low phytotoxicity. SAR showed that free alcohols and not O-protected compounds significantly influence the activity. Hence, a-methyl-a-1,2,4-triazole emerged as novel compound to develop new ketone-triazole-type antifungal agents for the management of Fusarium Dieback disease Resumen. Fusarium Dieback es una nueva enfermedad letal transmitida por insectos que actúan como vectores y puede atacar a más de 300 especies de árboles, incluidos los árboles de aguacate. Recientemente, este problema ha atraído la atención de los químicos sintéticos para desarrollar nuevos agentes antifúngicos triazólicos debido a la resistencia severa que desarrollan los insectos a los agentes antifúngicos triazólicos "clásicos". Durante este trabajo, se sintetizaron nuevos triazoles antifúngicos que contienen un grupo p-trifluorometilfenilo y se caracterizaron por métodos espectroscópicos y espectrométricos. La mayoría de los compuestos diana sintetizados mostraron una actividad inhibidora de modesta a buena y menos fitotoxicidad en comparación con el propiconazol que es comercialmente disponible; en particular, los compuestos 7 y 13 mostraron ser activos contra Fusarium solani y Fusarium euwallaceae. Los resultados mostraron que los compuestos 7, 13 y 4 tienen un gran potencial para desarrollarse como nuevos agentes antifúngicos debido a la buena actividad antifúngica y su baja fitotoxicidad. SAR mostró que los alcoholes libres y no los compuestos O-protegidos influyen significativamente en la actividad. Por lo tanto, el α-metil-α-1,2,4-triazol surgió como un nuevo compuesto líder para desarrollar nuevos agentes antifúngicos tipo cetona-triazol para el tratamiento de la enfermedad Fusarium Dieback.

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“…(Pericherla et al, 2012) These phenacyl bromides (1a-f) were treated with NaN 3 to afford 2-azido-1-phenylethanones (2a-f). The azide substitution is a straightforward reaction with excellent yields, and they were reduced by NaBH 4 to give corresponding alcohols (3a-f).…”

Section: Resultsmentioning

confidence: 99%

Click chemistry inspired synthesis of piperazine-triazole derivatives and evaluation of their antimicrobial activities

et al. 2015

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A series of novel piperazine-1,2,3-triazole derivatives, which entailed the bioisosteric replacement of the imidazole moiety and hybridization of two drug scaffolds was prepared by employing the regioselective copper (I)-catalysed azide-alkyne 1,3-dipolar cycloaddition reaction. The synthesized compounds were evaluated for antibacterial activities against Gram-negative (E. Coli and P. Putida), Gram-positive S. Aureus bacteria and fungicidal activities against F. oxysporum, F. gramillarium and F. monalliforme fungi. Compound 7ac 0 exhibited moderate but promising antibacterial activity against Gram-negative bacteria and fungicidal activity against F. oxysporum and F. gramillarium.

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Click chemistry inspired structural modification of azole antifungal agents to synthesize novel ‘drug like’ molecules

Cited by 30 publications

References 24 publications

Design and Applications of an Efficient Amphiphilic “Click” Cu^I Catalyst in Water

Design and Applications of an Efficient Amphiphilic “Click” Cu^I Catalyst in Water

Design, synthesis and biological evaluation of novel fungicides for the management of Fusarium DieBack disease

Click chemistry inspired synthesis of piperazine-triazole derivatives and evaluation of their antimicrobial activities

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Click chemistry inspired structural modification of azole antifungal agents to synthesize novel ‘drug like’ molecules

Cited by 30 publications

References 24 publications

Design and Applications of an Efficient Amphiphilic “Click” CuI Catalyst in Water

Design and Applications of an Efficient Amphiphilic “Click” CuI Catalyst in Water

Design, synthesis and biological evaluation of novel fungicides for the management of Fusarium DieBack disease

Click chemistry inspired synthesis of piperazine-triazole derivatives and evaluation of their antimicrobial activities

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Product

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Design and Applications of an Efficient Amphiphilic “Click” Cu^I Catalyst in Water

Design and Applications of an Efficient Amphiphilic “Click” Cu^I Catalyst in Water