Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents

New 4-(aroyloxyalkanoyl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-ones ( 5) were cyclized to 4-(2-aryl-5-unsubstituted/substituted oxazol-4-yl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-ones ( 6) employing the Davidson procedure. Preliminary evaluation of analgesic activity revealed that the effect of 4-(2-phe...

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Published in:European journal of medicinal chemistry 2000-03, Vol.35 (3), p.359-364
Main Authors: Gürsoy, Aysel, Demirayak, Şeref, Çapan, Gültaze, Erol, Kevser, Vural, Kamil
Format: Article
Language:English
Subjects:
Acetic Acid
analgesic activity
Analgesics
Analgesics, Non-Narcotic - chemical synthesis
Analgesics, Non-Narcotic - pharmacology
Animals
Biological and medical sciences
Edema - chemically induced
Edema - prevention & control
Female
Formaldehyde
Male
Medical sciences
Mice
Neuropharmacology
oxazole
Pain Measurement - drug effects
Pharmacology. Drug treatments
Pyrazoles - chemical synthesis
Pyrazoles - pharmacology
pyrazolin-5-one
Structure-Activity Relationship
synthesis
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cited_by cdi_FETCH-LOGICAL-c456t-3b02a97162e2aa7171d6834316c6e5e500fa6858f5b58189d218afd0050cb3f83
cites cdi_FETCH-LOGICAL-c456t-3b02a97162e2aa7171d6834316c6e5e500fa6858f5b58189d218afd0050cb3f83
container_end_page 364
container_issue 3
container_start_page 359
container_title European journal of medicinal chemistry
container_volume 35
creator Gürsoy, Aysel
Demirayak, Şeref
Çapan, Gültaze
Erol, Kevser
Vural, Kamil
description New 4-(aroyloxyalkanoyl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-ones ( 5) were cyclized to 4-(2-aryl-5-unsubstituted/substituted oxazol-4-yl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-ones ( 6) employing the Davidson procedure. Preliminary evaluation of analgesic activity revealed that the effect of 4-(2-phenyl-5-ethyloxazol-4-yl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 4-[2-(4-chlorophenyl)-5-ethyloxazol-4-yl]-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one on acetic acid induced writhing was superior to that of antypyrine and aminopyrine. 4-[2-(4-Chlorophenyl)-5-methyloxazol-4-yl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 4-[2-(4-methoxyphenyl)-5-ethyloxazol-4-yl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one were more potent than aminopyrine, whereas 4-(2-phenyl-5-methyloxazol-4-yl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 4-[2-(4-methoxyphenyl)-5-methyl-oxazol-4-yl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one were not as active (modified Koster's Test; 0.19–0.21 mmol.kg –1). None of the selected entries showed inhibition of formaldehyde-induced paw oedema.
doi_str_mv 10.1016/S0223-5234(00)00117-3
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Drug treatments</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - pharmacology</topic><topic>pyrazolin-5-one</topic><topic>Structure-Activity Relationship</topic><topic>synthesis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Gürsoy, Aysel</creatorcontrib><creatorcontrib>Demirayak, Şeref</creatorcontrib><creatorcontrib>Çapan, Gültaze</creatorcontrib><creatorcontrib>Erol, Kevser</creatorcontrib><creatorcontrib>Vural, Kamil</creatorcontrib><collection>Pascal-Francis</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>European journal of medicinal chemistry</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Gürsoy, Aysel</au><au>Demirayak, Şeref</au><au>Çapan, Gültaze</au><au>Erol, Kevser</au><au>Vural, Kamil</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2000-03-01</date><risdate>2000</risdate><volume>35</volume><issue>3</issue><spage>359</spage><epage>364</epage><pages>359-364</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>New 4-(aroyloxyalkanoyl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-ones ( 5) were cyclized to 4-(2-aryl-5-unsubstituted/substituted oxazol-4-yl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-ones ( 6) employing the Davidson procedure. Preliminary evaluation of analgesic activity revealed that the effect of 4-(2-phenyl-5-ethyloxazol-4-yl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 4-[2-(4-chlorophenyl)-5-ethyloxazol-4-yl]-2,3-dimethyl-1-phenyl-3-pyrazoline-5-one on acetic acid induced writhing was superior to that of antypyrine and aminopyrine. 4-[2-(4-Chlorophenyl)-5-methyloxazol-4-yl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 4-[2-(4-methoxyphenyl)-5-ethyloxazol-4-yl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one were more potent than aminopyrine, whereas 4-(2-phenyl-5-methyloxazol-4-yl)-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 4-[2-(4-methoxyphenyl)-5-methyl-oxazol-4-yl]-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one were not as active (modified Koster's Test; 0.19–0.21 mmol.kg –1). None of the selected entries showed inhibition of formaldehyde-induced paw oedema.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>10785562</pmid><doi>10.1016/S0223-5234(00)00117-3</doi><tpages>6</tpages></addata></record>
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identifier ISSN: 0223-5234
ispartof European journal of medicinal chemistry, 2000-03, Vol.35 (3), p.359-364
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1768-3254
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source ScienceDirect Journals
subjects Acetic Acid
analgesic activity
Analgesics
Analgesics, Non-Narcotic - chemical synthesis
Analgesics, Non-Narcotic - pharmacology
Animals
Biological and medical sciences
Edema - chemically induced
Edema - prevention & control
Female
Formaldehyde
Male
Medical sciences
Mice
Neuropharmacology
oxazole
Pain Measurement - drug effects
Pharmacology. Drug treatments
Pyrazoles - chemical synthesis
Pyrazoles - pharmacology
pyrazolin-5-one
Structure-Activity Relationship
synthesis
title Synthesis and preliminary evaluation of new 5-pyrazolinone derivatives as analgesic agents
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