Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors

Yasemin Dündar; Serdar Ünlü; Erden Banoǧlu; Antonio Entrena; Gabriele Costantino; Maria Teresa Nunez; Francisco Ledo; M. Fethi Şahin; Ningur Noyanalpan

doi:10.1016/j.ejmech.2008.10.039

Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors

Yasemin Dündar^*
, Serdar Ünlü
, Erden Banoǧlu
, Antonio Entrena
, Gabriele Costantino
, Maria Teresa Nunez
, Francisco Ledo
, M. Fethi Şahin
, Ningur Noyanalpan

^*Corresponding author for this work

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

30 Citations (Scopus)

Abstract

A series of 3-unsubstituted/substituted-4,5-diphenyl-2-oxo-3H-1,3-oxazole derivatives were prepared as selective cyclooxygenase-2 (COX-2) inhibitors. Among the synthesized compounds, 4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzensulfonamide (compound 6) showed selective COX-2 inhibition with a selectivity index of >50 (IC₅₀COX-1 = >100 μm, IC₅₀COX-2 = 2 μm) in purified enzyme (PE) assay. Compound 6 also exhibited selective COX-2 inhibition in human whole blood assay. Molecular docking studies showed that 6 can be docked into the COX-2 binding site thus providing the molecular basis for its activity.

Original language	English
Pages (from-to)	1830-1837
Number of pages	8
Journal	European Journal of Medicinal Chemistry
Volume	44
Issue number	5
DOIs	https://doi.org/10.1016/j.ejmech.2008.10.039
Publication status	Published - May 2009
Externally published	Yes

Keywords

4,5-Diphenyloxazolone
COX-1
COX-2
Cyclooxygenase inhibition
Docking

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

Access to Document

10.1016/j.ejmech.2008.10.039

Cite this

@article{8e34656985484bcca5ba0731acff6644,

title = "Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors",

abstract = "A series of 3-unsubstituted/substituted-4,5-diphenyl-2-oxo-3H-1,3-oxazole derivatives were prepared as selective cyclooxygenase-2 (COX-2) inhibitors. Among the synthesized compounds, 4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzensulfonamide (compound 6) showed selective COX-2 inhibition with a selectivity index of >50 (IC50COX-1 = >100 μm, IC50COX-2 = 2 μm) in purified enzyme (PE) assay. Compound 6 also exhibited selective COX-2 inhibition in human whole blood assay. Molecular docking studies showed that 6 can be docked into the COX-2 binding site thus providing the molecular basis for its activity.",

keywords = "4,5-Diphenyloxazolone, COX-1, COX-2, Cyclooxygenase inhibition, Docking",

author = "Yasemin D{\"u}ndar and Serdar {\"U}nl{\"u} and Erden Banoǧlu and Antonio Entrena and Gabriele Costantino and Nunez, \{Maria Teresa\} and Francisco Ledo and {\c S}ahin, \{M. Fethi\} and Ningur Noyanalpan",

year = "2009",

month = may,

doi = "10.1016/j.ejmech.2008.10.039",

language = "English",

volume = "44",

pages = "1830--1837",

journal = "European Journal of Medicinal Chemistry",

issn = "0223-5234",

publisher = "Elsevier Masson s.r.l.",

number = "5",

}

TY - JOUR

T1 - Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors

AU - Dündar, Yasemin

AU - Ünlü, Serdar

AU - Banoǧlu, Erden

AU - Entrena, Antonio

AU - Costantino, Gabriele

AU - Nunez, Maria Teresa

AU - Ledo, Francisco

AU - Şahin, M. Fethi

AU - Noyanalpan, Ningur

PY - 2009/5

Y1 - 2009/5

N2 - A series of 3-unsubstituted/substituted-4,5-diphenyl-2-oxo-3H-1,3-oxazole derivatives were prepared as selective cyclooxygenase-2 (COX-2) inhibitors. Among the synthesized compounds, 4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzensulfonamide (compound 6) showed selective COX-2 inhibition with a selectivity index of >50 (IC50COX-1 = >100 μm, IC50COX-2 = 2 μm) in purified enzyme (PE) assay. Compound 6 also exhibited selective COX-2 inhibition in human whole blood assay. Molecular docking studies showed that 6 can be docked into the COX-2 binding site thus providing the molecular basis for its activity.

AB - A series of 3-unsubstituted/substituted-4,5-diphenyl-2-oxo-3H-1,3-oxazole derivatives were prepared as selective cyclooxygenase-2 (COX-2) inhibitors. Among the synthesized compounds, 4-(4-phenyl-3-methyl-2-oxo-3H-1,3-oxazol-5-yl)benzensulfonamide (compound 6) showed selective COX-2 inhibition with a selectivity index of >50 (IC50COX-1 = >100 μm, IC50COX-2 = 2 μm) in purified enzyme (PE) assay. Compound 6 also exhibited selective COX-2 inhibition in human whole blood assay. Molecular docking studies showed that 6 can be docked into the COX-2 binding site thus providing the molecular basis for its activity.

KW - 4,5-Diphenyloxazolone

KW - COX-1

KW - COX-2

KW - Cyclooxygenase inhibition

KW - Docking

UR - https://www.scopus.com/pages/publications/62549162166

U2 - 10.1016/j.ejmech.2008.10.039

DO - 10.1016/j.ejmech.2008.10.039

M3 - Article

C2 - 19084295

AN - SCOPUS:62549162166

SN - 0223-5234

VL - 44

SP - 1830

EP - 1837

JO - European Journal of Medicinal Chemistry

JF - European Journal of Medicinal Chemistry

IS - 5

ER -

Synthesis and biological evaluation of 4,5-diphenyloxazolone derivatives on route towards selective COX-2 inhibitors

Abstract

Keywords

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this