Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines
The synthesis of a new series of 4-arylhydrazono-2-pyrazoline-5-ones 7–24 and 22a is described. Structures of the synthesized compounds were confirmed using UV, IR, 1H-NMR, 13C-NMR and EI-mass spectral data. These compounds were tested in vitro against one Gram-positive and two Gram-negative bacteri...
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| Veröffentlicht in: | European journal of medicinal chemistry 2000-07, Vol.35 (7), p.761-771 |
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| container_title | European journal of medicinal chemistry |
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| creator | Güniz Küçükgüzel, Ş Rollas, Sevim Erdeniz, Habibe Kiraz, Muammer Cevdet Ekinci, A Vidin, Aylin |
| description | The synthesis of a new series of 4-arylhydrazono-2-pyrazoline-5-ones
7–24 and
22a is described. Structures of the synthesized compounds were confirmed using UV, IR,
1H-NMR,
13C-NMR and EI-mass spectral data. These compounds were tested in vitro against one Gram-positive and two Gram-negative bacterial strains, two mycobacterial strains and a fungus,
Candida albicans. Compound
22 was found to be more active against
Staphylococcus aureus than the other compounds at a concentration of 15.6 μg/mL. Some related compounds were evaluated for anticonvulsant activity. Compound
11 showed 40% protection against pentylenetetrazole-induced seizures in albino Swiss mice. In vitro antituberculosis activity of 4-arylhydrazono-2-pyrazoline-5-ones
7–12,
14–24,
22a and coupling products
6a–f were tested on
Mycobacterium tuberculosis H37Rv. Of these compounds, only
24, which exhibited > 90% inhibition in the primary screen at 12.5 μg/mL against this strain was re-examined for determination of its actual MIC. However, level II assay revealed that the MIC value was not less than 12.5 μg/mL. The same compound was also tested against
Mycobacterium avium, which was observed not to be susceptible to
24. |
| doi_str_mv | 10.1016/S0223-5234(00)90179-X |
| format | Article |
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7–24 and
22a is described. Structures of the synthesized compounds were confirmed using UV, IR,
1H-NMR,
13C-NMR and EI-mass spectral data. These compounds were tested in vitro against one Gram-positive and two Gram-negative bacterial strains, two mycobacterial strains and a fungus,
Candida albicans. Compound
22 was found to be more active against
Staphylococcus aureus than the other compounds at a concentration of 15.6 μg/mL. Some related compounds were evaluated for anticonvulsant activity. Compound
11 showed 40% protection against pentylenetetrazole-induced seizures in albino Swiss mice. In vitro antituberculosis activity of 4-arylhydrazono-2-pyrazoline-5-ones
7–12,
14–24,
22a and coupling products
6a–f were tested on
Mycobacterium tuberculosis H37Rv. Of these compounds, only
24, which exhibited > 90% inhibition in the primary screen at 12.5 μg/mL against this strain was re-examined for determination of its actual MIC. However, level II assay revealed that the MIC value was not less than 12.5 μg/mL. The same compound was also tested against
Mycobacterium avium, which was observed not to be susceptible to
24.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/S0223-5234(00)90179-X</identifier><identifier>PMID: 10960193</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>4-arylhydrazono-2-pyrazoline-5-one ; Amines - chemistry ; Animals ; Anti-Infective Agents - chemical synthesis ; Anti-Infective Agents - chemistry ; Anti-Infective Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; anticonvulsant activity ; Anticonvulsants - chemical synthesis ; Anticonvulsants - chemistry ; Anticonvulsants - pharmacology ; Anticonvulsants. Antiepileptics. Antiparkinson agents ; Antifungal agents ; antimicrobial activity ; BACTEC 460 radiometric system ; Biological and medical sciences ; Female ; Heterocyclic Compounds - chemistry ; Magnetic Resonance Spectroscopy ; Male ; Medical sciences ; Mice ; Molecular Structure ; Neuropharmacology ; Pharmacology. Drug treatments ; Pyrazoles - chemical synthesis ; Pyrazoles - chemistry ; Pyrazoles - pharmacology ; Radiometry ; reductive cleavage ; Spectrum Analysis</subject><ispartof>European journal of medicinal chemistry, 2000-07, Vol.35 (7), p.761-771</ispartof><rights>2000 Éditions scientifiques et médicales Elsevier SAS</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c456t-b9a1fb566152de2ad618714fa7eb12eb424158ba2f5a795dc9051fe5e0922eb43</citedby><cites>FETCH-LOGICAL-c456t-b9a1fb566152de2ad618714fa7eb12eb424158ba2f5a795dc9051fe5e0922eb43</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://www.sciencedirect.com/science/article/pii/S022352340090179X$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,776,780,3537,27901,27902,65306</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1423719$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10960193$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Güniz Küçükgüzel, Ş</creatorcontrib><creatorcontrib>Rollas, Sevim</creatorcontrib><creatorcontrib>Erdeniz, Habibe</creatorcontrib><creatorcontrib>Kiraz, Muammer</creatorcontrib><creatorcontrib>Cevdet Ekinci, A</creatorcontrib><creatorcontrib>Vidin, Aylin</creatorcontrib><title>Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>The synthesis of a new series of 4-arylhydrazono-2-pyrazoline-5-ones
7–24 and
22a is described. Structures of the synthesized compounds were confirmed using UV, IR,
1H-NMR,
13C-NMR and EI-mass spectral data. These compounds were tested in vitro against one Gram-positive and two Gram-negative bacterial strains, two mycobacterial strains and a fungus,
Candida albicans. Compound
22 was found to be more active against
Staphylococcus aureus than the other compounds at a concentration of 15.6 μg/mL. Some related compounds were evaluated for anticonvulsant activity. Compound
11 showed 40% protection against pentylenetetrazole-induced seizures in albino Swiss mice. In vitro antituberculosis activity of 4-arylhydrazono-2-pyrazoline-5-ones
7–12,
14–24,
22a and coupling products
6a–f were tested on
Mycobacterium tuberculosis H37Rv. Of these compounds, only
24, which exhibited > 90% inhibition in the primary screen at 12.5 μg/mL against this strain was re-examined for determination of its actual MIC. However, level II assay revealed that the MIC value was not less than 12.5 μg/mL. The same compound was also tested against
Mycobacterium avium, which was observed not to be susceptible to
24.</description><subject>4-arylhydrazono-2-pyrazoline-5-one</subject><subject>Amines - chemistry</subject><subject>Animals</subject><subject>Anti-Infective Agents - chemical synthesis</subject><subject>Anti-Infective Agents - chemistry</subject><subject>Anti-Infective Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>anticonvulsant activity</subject><subject>Anticonvulsants - chemical synthesis</subject><subject>Anticonvulsants - chemistry</subject><subject>Anticonvulsants - pharmacology</subject><subject>Anticonvulsants. Antiepileptics. Antiparkinson agents</subject><subject>Antifungal agents</subject><subject>antimicrobial activity</subject><subject>BACTEC 460 radiometric system</subject><subject>Biological and medical sciences</subject><subject>Female</subject><subject>Heterocyclic Compounds - chemistry</subject><subject>Magnetic Resonance Spectroscopy</subject><subject>Male</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Molecular Structure</subject><subject>Neuropharmacology</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrazoles - chemical synthesis</subject><subject>Pyrazoles - chemistry</subject><subject>Pyrazoles - pharmacology</subject><subject>Radiometry</subject><subject>reductive cleavage</subject><subject>Spectrum Analysis</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2000</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkcFu1DAQhi1ERbcLjwDyASGQarCdONmcKlQVilSJQ0HqzZrYY9YoiYOdXSl9DV4Yp7sCbj3Z8v_9M55_CHkp-HvBRfXhlktZMCWL8i3n7xou6obdPSErUVcbVkhVPiWrv8gpOUvpJ-dcVZw_I6eCNxUXTbEiv2_nYdpi8umcmi1EMBNGfw-TDwOFwdIxP_ZgQhd-eAMdHWMYMU4eEw2OptAjLRnEudvONsJ9GAKTbJyXa-cHZIqFAanNRfe56H6xtRNkxVIXQ0-3mBsGM5vOGwp9FtJzcuKgS_jieK7J909X3y6v2c3Xz18uP94wU6pqYm0DwrWqqoSSFiXYSmxqUTqosRUS21KWQm1akE5B3ShrGq6EQ4W8kYtcrMmbQ908068dpkn3PhnsOhgw7JKupRRKFVUG1QE0MaQU0ekx-j4PrQXXyzb0wzb0ErXmXD9sQ99l36tjg13bo_3PdYg_A6-PAKQcroswGJ_-caUs6sytycUBw5zG3mPUyXgcDFof0UzaBv_IT_4ATcGqmA</recordid><startdate>20000701</startdate><enddate>20000701</enddate><creator>Güniz Küçükgüzel, Ş</creator><creator>Rollas, Sevim</creator><creator>Erdeniz, Habibe</creator><creator>Kiraz, Muammer</creator><creator>Cevdet Ekinci, A</creator><creator>Vidin, Aylin</creator><general>Elsevier Masson SAS</general><general>Elsevier</general><scope>IQODW</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20000701</creationdate><title>Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines</title><author>Güniz Küçükgüzel, Ş ; Rollas, Sevim ; Erdeniz, Habibe ; Kiraz, Muammer ; Cevdet Ekinci, A ; Vidin, Aylin</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c456t-b9a1fb566152de2ad618714fa7eb12eb424158ba2f5a795dc9051fe5e0922eb43</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2000</creationdate><topic>4-arylhydrazono-2-pyrazoline-5-one</topic><topic>Amines - chemistry</topic><topic>Animals</topic><topic>Anti-Infective Agents - chemical synthesis</topic><topic>Anti-Infective Agents - chemistry</topic><topic>Anti-Infective Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>anticonvulsant activity</topic><topic>Anticonvulsants - chemical synthesis</topic><topic>Anticonvulsants - chemistry</topic><topic>Anticonvulsants - pharmacology</topic><topic>Anticonvulsants. Antiepileptics. Antiparkinson agents</topic><topic>Antifungal agents</topic><topic>antimicrobial activity</topic><topic>BACTEC 460 radiometric system</topic><topic>Biological and medical sciences</topic><topic>Female</topic><topic>Heterocyclic Compounds - chemistry</topic><topic>Magnetic Resonance Spectroscopy</topic><topic>Male</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Molecular Structure</topic><topic>Neuropharmacology</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrazoles - chemical synthesis</topic><topic>Pyrazoles - chemistry</topic><topic>Pyrazoles - pharmacology</topic><topic>Radiometry</topic><topic>reductive cleavage</topic><topic>Spectrum Analysis</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Güniz Küçükgüzel, Ş</creatorcontrib><creatorcontrib>Rollas, Sevim</creatorcontrib><creatorcontrib>Erdeniz, Habibe</creatorcontrib><creatorcontrib>Kiraz, Muammer</creatorcontrib><creatorcontrib>Cevdet Ekinci, A</creatorcontrib><creatorcontrib>Vidin, Aylin</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>Güniz Küçükgüzel, Ş</au><au>Rollas, Sevim</au><au>Erdeniz, Habibe</au><au>Kiraz, Muammer</au><au>Cevdet Ekinci, A</au><au>Vidin, Aylin</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2000-07-01</date><risdate>2000</risdate><volume>35</volume><issue>7</issue><spage>761</spage><epage>771</epage><pages>761-771</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>The synthesis of a new series of 4-arylhydrazono-2-pyrazoline-5-ones
7–24 and
22a is described. Structures of the synthesized compounds were confirmed using UV, IR,
1H-NMR,
13C-NMR and EI-mass spectral data. These compounds were tested in vitro against one Gram-positive and two Gram-negative bacterial strains, two mycobacterial strains and a fungus,
Candida albicans. Compound
22 was found to be more active against
Staphylococcus aureus than the other compounds at a concentration of 15.6 μg/mL. Some related compounds were evaluated for anticonvulsant activity. Compound
11 showed 40% protection against pentylenetetrazole-induced seizures in albino Swiss mice. In vitro antituberculosis activity of 4-arylhydrazono-2-pyrazoline-5-ones
7–12,
14–24,
22a and coupling products
6a–f were tested on
Mycobacterium tuberculosis H37Rv. Of these compounds, only
24, which exhibited > 90% inhibition in the primary screen at 12.5 μg/mL against this strain was re-examined for determination of its actual MIC. However, level II assay revealed that the MIC value was not less than 12.5 μg/mL. The same compound was also tested against
Mycobacterium avium, which was observed not to be susceptible to
24.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>10960193</pmid><doi>10.1016/S0223-5234(00)90179-X</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
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| subjects | 4-arylhydrazono-2-pyrazoline-5-one Amines - chemistry Animals Anti-Infective Agents - chemical synthesis Anti-Infective Agents - chemistry Anti-Infective Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents anticonvulsant activity Anticonvulsants - chemical synthesis Anticonvulsants - chemistry Anticonvulsants - pharmacology Anticonvulsants. Antiepileptics. Antiparkinson agents Antifungal agents antimicrobial activity BACTEC 460 radiometric system Biological and medical sciences Female Heterocyclic Compounds - chemistry Magnetic Resonance Spectroscopy Male Medical sciences Mice Molecular Structure Neuropharmacology Pharmacology. Drug treatments Pyrazoles - chemical synthesis Pyrazoles - chemistry Pyrazoles - pharmacology Radiometry reductive cleavage Spectrum Analysis |
| title | Synthesis, characterization and pharmacological properties of some 4-arylhydrazono-2-pyrazoline-5-one derivatives obtained from heterocyclic amines |
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