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^*

^*Bu çalışma için yazışmadan sorumlu yazar

Kimya Bölümü

Istanbul Technical University

Araştırma sonucu: ???type-name??? › Makale › bilirkişi

2 Atıf (Scopus)

Özet

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.

Orijinal dil	İngilizce
Sayfa (başlangıç-bitiş)	7278-7283
Sayfa sayısı	6
Dergi	ChemistrySelect
Hacim	4
Basın numarası	24
DOI'lar	https://doi.org/10.1002/slct.201901403
Yayın durumu	Yayınlandı - 28 Haz 2019

Bibliyografik not

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

Finansman

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.

Finansörler	Finansör numarası
Istanbul Teknik Üniversitesi	5004722017

Belgeye Erişim

10.1002/slct.201901403

Diğer Dosyalar ve Linkler

Link to publication in Scopus

Alıntı Yap

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title = "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 = "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.",

keywords = "Amberlyst-15, Benzodioxinones, Click reactions, Hsp90, Triazoles",

author = "Hande Gunduz and Volkan Kumbaraci and Yılmaz {\"O}zkılı{\c c} and Nurcan T{\"u}z{\"u}n and Naciye Talinli",

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

year = "2019",

month = jun,

day = "28",

doi = "10.1002/slct.201901403",

language = "English",

volume = "4",

pages = "7278--7283",

journal = "ChemistrySelect",

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TY - JOUR

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

KW - Triazoles

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U2 - 10.1002/slct.201901403

DO - 10.1002/slct.201901403

M3 - Article

AN - SCOPUS:85068042054

SN - 2365-6549

VL - 4

SP - 7278

EP - 7283

JO - ChemistrySelect

JF - ChemistrySelect

IS - 24

ER -

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

Özet

Bibliyografik not

Finansman

Belgeye Erişim

Diğer Dosyalar ve Linkler

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