Abstract

Pyrazolylbenzotriazinones are endowed with structural analogy with the COX-2 selective inhibitor celecoxib. Considering that our research group has long been interested in the 3-pyrazolyl-substituted benzotriazinones as anti-inflammatory agents, six new pyrazolylbenzotriazinone derivatives 16a-c and 18a-c have been prepared by reacting the opportune ethyl 5-(2-aminobenzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate or 5-(2-aminobenzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxyic acid with sodium nitrite in glacial acetic acid. The biological studies revealed a good pharmacological profile for some pyrazolylbenzotriazinones and, in the case of the ethyl 5-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)-1-pyridin-2-yl-1H-pyrazole-4-carboxylate 16a, a good COX-1/COX-2 selectivity. Molecular modeling studies confirmed the obtained biological results.
Lingua originaleEnglish
pagine (da-a)631-638
Numero di pagine7
RivistaArchiv der Pharmazie
Volume10
Stato di pubblicazionePublished - 2010

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Celecoxib
Sodium Nitrite
Cyclooxygenase 2 Inhibitors
Acetic Acid
Anti-Inflammatory Agents
Pharmacology
Acids
Research
pyrazole

All Science Journal Classification (ASJC) codes

  • Pharmaceutical Science
  • Drug Discovery

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title = "Pyrazolobenzotriazinones Derivatives as COX Inhibitors: Synthesis Biological Activity and Molecular Modeling Studies",
abstract = "Pyrazolylbenzotriazinones are endowed with structural analogy with the COX-2 selective inhibitor celecoxib. Considering that our research group has long been interested in the 3-pyrazolyl-substituted benzotriazinones as anti-inflammatory agents, six new pyrazolylbenzotriazinone derivatives 16a-c and 18a-c have been prepared by reacting the opportune ethyl 5-(2-aminobenzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate or 5-(2-aminobenzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxyic acid with sodium nitrite in glacial acetic acid. The biological studies revealed a good pharmacological profile for some pyrazolylbenzotriazinones and, in the case of the ethyl 5-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)-1-pyridin-2-yl-1H-pyrazole-4-carboxylate 16a, a good COX-1/COX-2 selectivity. Molecular modeling studies confirmed the obtained biological results.",
keywords = "2-(1H-pyrazol-1-yl)pyridines, 4(3H)-Benzotriazinones, docking, COX-2 inhibitors",
author = "Onofrio Migliara and Giuseppe Tringali and Benedetta Maggio and Demetrio Raffa and Carla Cannizzaro and Fabiana Plescia and Cascioferro, {Stella Maria} and Cusimano, {Maria Grazia} and Fulvio Plescia and Giuseppe Tringali",
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pages = "631--638",
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T1 - Pyrazolobenzotriazinones Derivatives as COX Inhibitors: Synthesis Biological Activity and Molecular Modeling Studies

AU - Migliara, Onofrio

AU - Tringali, Giuseppe

AU - Maggio, Benedetta

AU - Raffa, Demetrio

AU - Cannizzaro, Carla

AU - Plescia, Fabiana

AU - Cascioferro, Stella Maria

AU - Cusimano, Maria Grazia

AU - Plescia, Fulvio

AU - Tringali, Giuseppe

PY - 2010

Y1 - 2010

N2 - Pyrazolylbenzotriazinones are endowed with structural analogy with the COX-2 selective inhibitor celecoxib. Considering that our research group has long been interested in the 3-pyrazolyl-substituted benzotriazinones as anti-inflammatory agents, six new pyrazolylbenzotriazinone derivatives 16a-c and 18a-c have been prepared by reacting the opportune ethyl 5-(2-aminobenzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate or 5-(2-aminobenzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxyic acid with sodium nitrite in glacial acetic acid. The biological studies revealed a good pharmacological profile for some pyrazolylbenzotriazinones and, in the case of the ethyl 5-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)-1-pyridin-2-yl-1H-pyrazole-4-carboxylate 16a, a good COX-1/COX-2 selectivity. Molecular modeling studies confirmed the obtained biological results.

AB - Pyrazolylbenzotriazinones are endowed with structural analogy with the COX-2 selective inhibitor celecoxib. Considering that our research group has long been interested in the 3-pyrazolyl-substituted benzotriazinones as anti-inflammatory agents, six new pyrazolylbenzotriazinone derivatives 16a-c and 18a-c have been prepared by reacting the opportune ethyl 5-(2-aminobenzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxylate or 5-(2-aminobenzamido)-1-(pyridin-2-yl)-1H-pyrazole-4-carboxyic acid with sodium nitrite in glacial acetic acid. The biological studies revealed a good pharmacological profile for some pyrazolylbenzotriazinones and, in the case of the ethyl 5-(4-oxo-1,2,3-benzotriazin-3(4H)-yl)-1-pyridin-2-yl-1H-pyrazole-4-carboxylate 16a, a good COX-1/COX-2 selectivity. Molecular modeling studies confirmed the obtained biological results.

KW - 2-(1H-pyrazol-1-yl)pyridines, 4(3H)-Benzotriazinones, docking, COX-2 inhibitors

UR - http://hdl.handle.net/10447/52002

M3 - Article

VL - 10

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EP - 638

JO - Archiv der Pharmazie

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