Amberlyst-15-catalyzed Procedure for the Synthesis of Novel 2,4-Dihydroxybenzoyl-1,2,3-triazoles and Molecular Modelling Studies for Hsp-90 Inhibition

Hande Gunduz; Volkan Kumbaraci; Yılmaz Özkılıç; Nurcan Tüzün; Naciye Talinli

doi:10.1002/slct.201901403

Amberlyst-15-catalyzed Procedure for the Synthesis of Novel 2,4-Dihydroxybenzoyl-1,2,3-triazoles and Molecular Modelling Studies for Hsp-90 Inhibition

Hande Gunduz, Volkan Kumbaraci, Yılmaz Özkılıç, Nurcan Tüzün, Naciye Talinli^*

^*Corresponding author for this work

Department of Chemistry

Istanbul Technical University

Research output: Contribution to journal › Article › peer-review

2 Citations (Scopus)

Abstract

Novel 4-and 5-(2,4-dihydroxybenzoyl) triazoles were prepared from o-alkynoylresorcinols with by the cycloaddition reaction performed with metal free one step protocol using Bronsted acid Amberlyst-15 as catalyst for the first time. This procedure enables the synthesis of triazoles bearing o,p-dihydroxybenzoyl group without the need to protection of hydroxyl groups. Products were obtained in good to excellent yields and with the moderate regioisomeric ratios. In addition, Hsp90 inhibition activities of synthesized compounds were examined by molecular modelling studies and promising results were obtained.

Original language	English
Pages (from-to)	7278-7283
Number of pages	6
Journal	ChemistrySelect
Volume	4
Issue number	24
DOIs	https://doi.org/10.1002/slct.201901403
Publication status	Published - 28 Jun 2019

Bibliographical note

Publisher Copyright:
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Funding

WethanktoIstanbulTechnicalUniversityresearchfundsfor financialsupport.TheauthorsgratefullyacknowledgetheNa-tionalHighPerformanceComputingCenteratITU(Grant No.5004722017)forcomputationalsources. We thank to Istanbul Technical University research funds for financial support. The authors gratefully acknowledge the National High Performance Computing Center at ITU (Grant No.5004722017) for computational sources.

Funders	Funder number
Istanbul Teknik Üniversitesi	5004722017

Keywords

Amberlyst-15
Benzodioxinones
Click reactions
Hsp90
Triazoles

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10.1002/slct.201901403

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abstract = "Novel 4-and 5-(2,4-dihydroxybenzoyl) triazoles were prepared from o-alkynoylresorcinols with by the cycloaddition reaction performed with metal free one step protocol using Bronsted acid Amberlyst-15 as catalyst for the first time. This procedure enables the synthesis of triazoles bearing o,p-dihydroxybenzoyl group without the need to protection of hydroxyl groups. Products were obtained in good to excellent yields and with the moderate regioisomeric ratios. In addition, Hsp90 inhibition activities of synthesized compounds were examined by molecular modelling studies and promising results were obtained.",

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note = "Publisher Copyright: {\textcopyright} 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

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T1 - Amberlyst-15-catalyzed Procedure for the Synthesis of Novel 2,4-Dihydroxybenzoyl-1,2,3-triazoles and Molecular Modelling Studies for Hsp-90 Inhibition

AU - Gunduz, Hande

AU - Kumbaraci, Volkan

AU - Özkılıç, Yılmaz

AU - Tüzün, Nurcan

AU - Talinli, Naciye

PY - 2019/6/28

Y1 - 2019/6/28

N2 - Novel 4-and 5-(2,4-dihydroxybenzoyl) triazoles were prepared from o-alkynoylresorcinols with by the cycloaddition reaction performed with metal free one step protocol using Bronsted acid Amberlyst-15 as catalyst for the first time. This procedure enables the synthesis of triazoles bearing o,p-dihydroxybenzoyl group without the need to protection of hydroxyl groups. Products were obtained in good to excellent yields and with the moderate regioisomeric ratios. In addition, Hsp90 inhibition activities of synthesized compounds were examined by molecular modelling studies and promising results were obtained.

AB - Novel 4-and 5-(2,4-dihydroxybenzoyl) triazoles were prepared from o-alkynoylresorcinols with by the cycloaddition reaction performed with metal free one step protocol using Bronsted acid Amberlyst-15 as catalyst for the first time. This procedure enables the synthesis of triazoles bearing o,p-dihydroxybenzoyl group without the need to protection of hydroxyl groups. Products were obtained in good to excellent yields and with the moderate regioisomeric ratios. In addition, Hsp90 inhibition activities of synthesized compounds were examined by molecular modelling studies and promising results were obtained.

KW - Amberlyst-15

KW - Benzodioxinones

KW - Click reactions

KW - Hsp90

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Amberlyst-15-catalyzed Procedure for the Synthesis of Novel 2,4-Dihydroxybenzoyl-1,2,3-triazoles and Molecular Modelling Studies for Hsp-90 Inhibition

Abstract

Bibliographical note

Funding

Keywords

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