Optically active antifungal azoles: synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol

Upadhayaya, Ram Shankar; Sinha, Neelima; Jain, Sanjay; Kishore, Nawal; Chandra, Ramesh; Arora, Sadhna

doi:10.1016/j.bmc.2004.02.014

Cited by 170 publications

(41 citation statements)

References 26 publications

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“…Similarly, piperazine derivatives, containing tetrazole nucleus, have been reported as antifungal agents. 26 The details of the scaffold synthesis included coupling reaction, which was followed by reduction of nitro group and then cyclization.…”

Section: 24mentioning

confidence: 99%

Synthesis and biological activities of piperazine derivatives as antimicrobial and antifungal agents

Suryavanshi¹,

Rathore²

2017

Org. Commun.

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Abstract:Apart from thiazole, benzimidazole, and tetrazole family, some of the piperazine analogs also show significant pharmacophoric activities. The synthesis of piperazine through intermediate 3 occurred via coupling of substituted benzenethiol with chloro-nitrobenzene. The nitro group of the isolated intermediate was reduced via an iron-acetic acid system. The aniline intermediate was cyclized with bis(2-chloroethyl)amine hydrochloride to obtain piperazine moiety. The synthesized substituted piperazine derivatives were screened for antibacterial and antifungal activities. The antibacterial activity was tested against Staphylococcus aureus, Streptomyces epidermidis, Pseudomonas aeruginosa and Escherichia coli, and antifungal activity was tested against Candida albicans, Aspergillus niger, Aspergillus flavus and Aspergillus fumigatus. As a result, many of the synthesized compounds showed significant antimicrobial and antifungal properties.

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Section: 24mentioning

confidence: 99%

Synthesis and biological activities of piperazine derivatives as antimicrobial and antifungal agents

Suryavanshi¹,

Rathore²

2017

Org. Commun.

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“…Their important biological activities include antifungal, [1][2][3][4][5][6] antibacterial, 7 anticancer 8 and antiviral, [9][10][11] H1/H2 histamine receptor blockers, cholinesterase active agents, central nervous system (CNS) stimulants, antianxiety and sedatives. [12][13] Antimycotic, fluconazole, itraconazole, ravuconazole and variconazole are therapeutically interesting drug candidates, including 1,2,4-triazole nucleus.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, in vitro Antiproliferative Activity, Binding Modeling of 1,2,4,-Triazoles as New Anti-Breast Cancer Agents

Genç¹,

Genç²,

Tekin³

et al. 2016

ACSi

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This article demonstrates the synthesis of 1,2,4-triazole derivatives and their applications in medicine particularly as anti-breast cancer agents which is a major issue of the present. The synthesized compounds were characterized by elemental analysis, FT-IR and NMR. DFT was used to study the quantum chemical calculations of geometries and vibrational wave numbers of 3-hydroxynaphthyl and p-tolyl substituted 1,2,4-triazoles in the ground state. The scaled harmonic vibrational frequencies obtained from the DFT method were compared with those of the FT-IR spectra and found good agreement. The synthesized 1,2,4-triazole-naphthyl hybrids were screened for the anticancer activity against MCF-7 breast cancer lines. Among them compounds 3 and 7 showed broad spectrum anticancer activity with IC 50 values 9.7 μM and 7.10 μM, respectively and their activity is comparable to that of the standard drugs. The molecular model for binding between the compounds (1-8) and the active site of BRCA2 was obtained on the basis of the computational docking results and the structure-activity relationship.

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“…The biological importance of quinazoline had already stimulated the medicinal chemists to consider it as a building block due to its broad range of pharmacological properties, such as antimicrobial [16][17][18] , anti-HIV and anti-TMV (Tobacco Mosaic Virus) 19,20 , antitubercular 21 , anticancer 22 , anti-inflammatory 23 , anticonvulsant 24 , antidepressant 25 , hypolipidemic 26 , antiulcer 27 , analgesic 28 and immunotropic activities 29 . Moreover, piperazine heterocycles are valuable structural units in drug research [30][31][32][33][34][35][36] . In context to the above rationale and in continuation of our ongoing program focused on finding new leads with anti-HIV activities [37][38][39][40][41][42] , a novel hybrid series of DATA molecules with a combination of different pharmacophores such as triazine, quinazoline and piperazine that are structurally related to anti-HIV lead compounds, i.e.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, antimicrobial activity and anti-HIV activity evaluation of novel hybrid quinazoline–triazine derivatives

Modh

Clercq

Pannecouque

et al. 2013

Journal of Enzyme Inhibition and Medicinal Chemistry

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Optically active antifungal azoles: synthesis and antifungal activity of (2R,3S)-2-(2,4-difluorophenyl)-3-(5-{2-[4-aryl-piperazin-1-yl]-ethyl}-tetrazol-2-yl/1-yl)-1-[1,2,4]-triazol-1-yl-butan-2-ol

Cited by 170 publications

References 26 publications

Synthesis and biological activities of piperazine derivatives as antimicrobial and antifungal agents

Synthesis and biological activities of piperazine derivatives as antimicrobial and antifungal agents

Design, Synthesis, in vitro Antiproliferative Activity, Binding Modeling of 1,2,4,-Triazoles as New Anti-Breast Cancer Agents

Design, synthesis, antimicrobial activity and anti-HIV activity evaluation of novel hybrid quinazoline–triazine derivatives

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