Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkersElectronic supplementary information (ESI) available: Copy of 1H NMR, 13C NMR, HRMS/elemental analysis of all the compounds. HPLC spectra of compound 6b and 6f. Graphs of anti-inflammatory studies. See DOI: 10.1039/c4ob01281j
Novel, non-steroidal anti-inflammatory drug (NSAID), acetaminophen conjugates 6a-l with amino acid linkers were synthesized utilizing benzotriazole chemistry. Biological data acquired for all the novel bis-conjugates showed (a) some bis-conjugates ( 6d , 6e , 6h , and 6k ) exhibit more potent anti-i...
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| creator | Tiwari, Anand D Panda, Siva S Girgis, Adel S Sahu, Sandhyamayee George, Riham F Srour, Aladdin M Starza, Brian La Asiri, Abdullah M Hall, C. Dennis Katritzky, Alan R |
| description | Novel, non-steroidal anti-inflammatory drug (NSAID), acetaminophen conjugates
6a-l
with amino acid linkers were synthesized utilizing benzotriazole chemistry. Biological data acquired for all the novel bis-conjugates showed (a) some bis-conjugates (
6d
,
6e
,
6h
, and
6k
) exhibit more potent anti-inflammatory activity than their parent drugs, (b) the potent bis-conjugates show no visible stomach lesions in contrast to parent drugs which are highly ulcerogenic, and (c) that the potent bio-active compounds have no mortality rates or toxic symptoms at 5 fold the applied anti-inflammatory dosage. A statistically significant QSAR model describing the anti-inflammatory properties of
6a-l
(
N
= 15,
n
= 3,
R
2
= 0.891,
R
2
cvOO = 0.770,
R
2
cvMO = 0.796,
F
= 29.904,
s
2
= 0.011) was obtained employing CODESSA-Pro that validated the observed bio-activity.
Twelve novel conjugates of NSAID linked by amino acid units to acetaminophen synthesized under microwave irradiation as potential anti-inflammatory agents. |
| doi_str_mv | 10.1039/c4ob01281j |
| format | Article |
| fullrecord | <record><control><sourceid>rsc</sourceid><recordid>TN_cdi_rsc_primary_c4ob01281j</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>c4ob01281j</sourcerecordid><originalsourceid>FETCH-rsc_primary_c4ob01281j3</originalsourceid><addsrcrecordid>eNqFkM1PAjEQxVejifhx8W4y3jQR2GURhBtZUEgAlfVOht1ZKXbbpi2Q_e8tH-rBRE-d5r28-b3xvMvArwR-2KomdTnzg9pDsDj0SkG92Sz792Hr6Huu-SfeqTEL3w9azUa9dDAcsUTLNa4I0BhmLKVgCmHn5D6AIoXXuDMBY5dpATIDIVfEYRx3Bl3AhCzmTEg1JwGJFIvlO1oysGZ2DlvFeVgKnIkP0qbHKbFaCpaAWSrFKSdhURfARCZ1jpZJATe9eHALuELGccapDZFU281BH8ajyR0EYbQb-pNRXKV9CnesyIsNtPMi5-AqOKZcyaVITQX6L8MIjNoQ4MbyJUFjtq3ZyCrwpFHNdwHCsrLD4pg7LukYNxdg5IJiIug-D9rw--bn3nGG3NDF_j3zrh57b1G_rE0yVZrlruz0xx7-r1__pU9VmoWfisKhlQ</addsrcrecordid><sourcetype>Enrichment Source</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype></control><display><type>article</type><title>Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkersElectronic supplementary information (ESI) available: Copy of 1H NMR, 13C NMR, HRMS/elemental analysis of all the compounds. HPLC spectra of compound 6b and 6f. Graphs of anti-inflammatory studies. See DOI: 10.1039/c4ob01281j</title><source>Royal Society Of Chemistry Journals 2008-</source><source>Alma/SFX Local Collection</source><creator>Tiwari, Anand D ; Panda, Siva S ; Girgis, Adel S ; Sahu, Sandhyamayee ; George, Riham F ; Srour, Aladdin M ; Starza, Brian La ; Asiri, Abdullah M ; Hall, C. Dennis ; Katritzky, Alan R</creator><creatorcontrib>Tiwari, Anand D ; Panda, Siva S ; Girgis, Adel S ; Sahu, Sandhyamayee ; George, Riham F ; Srour, Aladdin M ; Starza, Brian La ; Asiri, Abdullah M ; Hall, C. Dennis ; Katritzky, Alan R</creatorcontrib><description>Novel, non-steroidal anti-inflammatory drug (NSAID), acetaminophen conjugates
6a-l
with amino acid linkers were synthesized utilizing benzotriazole chemistry. Biological data acquired for all the novel bis-conjugates showed (a) some bis-conjugates (
6d
,
6e
,
6h
, and
6k
) exhibit more potent anti-inflammatory activity than their parent drugs, (b) the potent bis-conjugates show no visible stomach lesions in contrast to parent drugs which are highly ulcerogenic, and (c) that the potent bio-active compounds have no mortality rates or toxic symptoms at 5 fold the applied anti-inflammatory dosage. A statistically significant QSAR model describing the anti-inflammatory properties of
6a-l
(
N
= 15,
n
= 3,
R
2
= 0.891,
R
2
cvOO = 0.770,
R
2
cvMO = 0.796,
F
= 29.904,
s
2
= 0.011) was obtained employing CODESSA-Pro that validated the observed bio-activity.
Twelve novel conjugates of NSAID linked by amino acid units to acetaminophen synthesized under microwave irradiation as potential anti-inflammatory agents.</description><identifier>ISSN: 1477-0520</identifier><identifier>EISSN: 1477-0539</identifier><identifier>DOI: 10.1039/c4ob01281j</identifier><language>eng</language><creationdate>2014-08</creationdate><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>315,781,785,27926,27927</link.rule.ids></links><search><creatorcontrib>Tiwari, Anand D</creatorcontrib><creatorcontrib>Panda, Siva S</creatorcontrib><creatorcontrib>Girgis, Adel S</creatorcontrib><creatorcontrib>Sahu, Sandhyamayee</creatorcontrib><creatorcontrib>George, Riham F</creatorcontrib><creatorcontrib>Srour, Aladdin M</creatorcontrib><creatorcontrib>Starza, Brian La</creatorcontrib><creatorcontrib>Asiri, Abdullah M</creatorcontrib><creatorcontrib>Hall, C. Dennis</creatorcontrib><creatorcontrib>Katritzky, Alan R</creatorcontrib><title>Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkersElectronic supplementary information (ESI) available: Copy of 1H NMR, 13C NMR, HRMS/elemental analysis of all the compounds. HPLC spectra of compound 6b and 6f. Graphs of anti-inflammatory studies. See DOI: 10.1039/c4ob01281j</title><description>Novel, non-steroidal anti-inflammatory drug (NSAID), acetaminophen conjugates
6a-l
with amino acid linkers were synthesized utilizing benzotriazole chemistry. Biological data acquired for all the novel bis-conjugates showed (a) some bis-conjugates (
6d
,
6e
,
6h
, and
6k
) exhibit more potent anti-inflammatory activity than their parent drugs, (b) the potent bis-conjugates show no visible stomach lesions in contrast to parent drugs which are highly ulcerogenic, and (c) that the potent bio-active compounds have no mortality rates or toxic symptoms at 5 fold the applied anti-inflammatory dosage. A statistically significant QSAR model describing the anti-inflammatory properties of
6a-l
(
N
= 15,
n
= 3,
R
2
= 0.891,
R
2
cvOO = 0.770,
R
2
cvMO = 0.796,
F
= 29.904,
s
2
= 0.011) was obtained employing CODESSA-Pro that validated the observed bio-activity.
Twelve novel conjugates of NSAID linked by amino acid units to acetaminophen synthesized under microwave irradiation as potential anti-inflammatory agents.</description><issn>1477-0520</issn><issn>1477-0539</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2014</creationdate><recordtype>article</recordtype><sourceid/><recordid>eNqFkM1PAjEQxVejifhx8W4y3jQR2GURhBtZUEgAlfVOht1ZKXbbpi2Q_e8tH-rBRE-d5r28-b3xvMvArwR-2KomdTnzg9pDsDj0SkG92Sz792Hr6Huu-SfeqTEL3w9azUa9dDAcsUTLNa4I0BhmLKVgCmHn5D6AIoXXuDMBY5dpATIDIVfEYRx3Bl3AhCzmTEg1JwGJFIvlO1oysGZ2DlvFeVgKnIkP0qbHKbFaCpaAWSrFKSdhURfARCZ1jpZJATe9eHALuELGccapDZFU281BH8ajyR0EYbQb-pNRXKV9CnesyIsNtPMi5-AqOKZcyaVITQX6L8MIjNoQ4MbyJUFjtq3ZyCrwpFHNdwHCsrLD4pg7LukYNxdg5IJiIug-D9rw--bn3nGG3NDF_j3zrh57b1G_rE0yVZrlruz0xx7-r1__pU9VmoWfisKhlQ</recordid><startdate>20140827</startdate><enddate>20140827</enddate><creator>Tiwari, Anand D</creator><creator>Panda, Siva S</creator><creator>Girgis, Adel S</creator><creator>Sahu, Sandhyamayee</creator><creator>George, Riham F</creator><creator>Srour, Aladdin M</creator><creator>Starza, Brian La</creator><creator>Asiri, Abdullah M</creator><creator>Hall, C. Dennis</creator><creator>Katritzky, Alan R</creator><scope/></search><sort><creationdate>20140827</creationdate><title>Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkersElectronic supplementary information (ESI) available: Copy of 1H NMR, 13C NMR, HRMS/elemental analysis of all the compounds. HPLC spectra of compound 6b and 6f. Graphs of anti-inflammatory studies. See DOI: 10.1039/c4ob01281j</title><author>Tiwari, Anand D ; Panda, Siva S ; Girgis, Adel S ; Sahu, Sandhyamayee ; George, Riham F ; Srour, Aladdin M ; Starza, Brian La ; Asiri, Abdullah M ; Hall, C. Dennis ; Katritzky, Alan R</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-rsc_primary_c4ob01281j3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2014</creationdate><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Tiwari, Anand D</creatorcontrib><creatorcontrib>Panda, Siva S</creatorcontrib><creatorcontrib>Girgis, Adel S</creatorcontrib><creatorcontrib>Sahu, Sandhyamayee</creatorcontrib><creatorcontrib>George, Riham F</creatorcontrib><creatorcontrib>Srour, Aladdin M</creatorcontrib><creatorcontrib>Starza, Brian La</creatorcontrib><creatorcontrib>Asiri, Abdullah M</creatorcontrib><creatorcontrib>Hall, C. Dennis</creatorcontrib><creatorcontrib>Katritzky, Alan R</creatorcontrib></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Tiwari, Anand D</au><au>Panda, Siva S</au><au>Girgis, Adel S</au><au>Sahu, Sandhyamayee</au><au>George, Riham F</au><au>Srour, Aladdin M</au><au>Starza, Brian La</au><au>Asiri, Abdullah M</au><au>Hall, C. Dennis</au><au>Katritzky, Alan R</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkersElectronic supplementary information (ESI) available: Copy of 1H NMR, 13C NMR, HRMS/elemental analysis of all the compounds. HPLC spectra of compound 6b and 6f. Graphs of anti-inflammatory studies. See DOI: 10.1039/c4ob01281j</atitle><date>2014-08-27</date><risdate>2014</risdate><volume>12</volume><issue>37</issue><spage>7238</spage><epage>7249</epage><pages>7238-7249</pages><issn>1477-0520</issn><eissn>1477-0539</eissn><abstract>Novel, non-steroidal anti-inflammatory drug (NSAID), acetaminophen conjugates
6a-l
with amino acid linkers were synthesized utilizing benzotriazole chemistry. Biological data acquired for all the novel bis-conjugates showed (a) some bis-conjugates (
6d
,
6e
,
6h
, and
6k
) exhibit more potent anti-inflammatory activity than their parent drugs, (b) the potent bis-conjugates show no visible stomach lesions in contrast to parent drugs which are highly ulcerogenic, and (c) that the potent bio-active compounds have no mortality rates or toxic symptoms at 5 fold the applied anti-inflammatory dosage. A statistically significant QSAR model describing the anti-inflammatory properties of
6a-l
(
N
= 15,
n
= 3,
R
2
= 0.891,
R
2
cvOO = 0.770,
R
2
cvMO = 0.796,
F
= 29.904,
s
2
= 0.011) was obtained employing CODESSA-Pro that validated the observed bio-activity.
Twelve novel conjugates of NSAID linked by amino acid units to acetaminophen synthesized under microwave irradiation as potential anti-inflammatory agents.</abstract><doi>10.1039/c4ob01281j</doi><tpages>12</tpages></addata></record> |
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| source | Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection |
| title | Microwave assisted synthesis and QSAR study of novel NSAID acetaminophen conjugates with amino acid linkersElectronic supplementary information (ESI) available: Copy of 1H NMR, 13C NMR, HRMS/elemental analysis of all the compounds. HPLC spectra of compound 6b and 6f. Graphs of anti-inflammatory studies. See DOI: 10.1039/c4ob01281j |
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