2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity
2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides ( 1– 17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxy-phenyl)-2(3 H)-pyrrolones ( 18– 23) and...
Gespeichert in:
| Veröffentlicht in: | European journal of medicinal chemistry 2005-12, Vol.40 (12), p.1394-1404 |
|---|---|
| Hauptverfasser: | , , , |
| Format: | Artikel |
| Sprache: | eng |
| Schlagworte: | |
| Online-Zugang: | Volltext |
| Tags: |
Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
|
| container_end_page | 1404 |
|---|---|
| container_issue | 12 |
| container_start_page | 1394 |
| container_title | European journal of medicinal chemistry |
| container_volume | 40 |
| creator | Husain, Asif Khan, M.S.Y. Hasan, S.M. Alam, M.M. |
| description | 2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (
1–
17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxy-phenyl)-2(3
H)-pyrrolones (
18–
23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3
H)-pyrrolones (
24–
29) respectively, which were characterized on the basis of
1H-,
13C-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for anti-inflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (
5,
6,
7,
25 and
26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against
Staphylococcus aureus and
Escherichia coli as well as antifungal activity against
Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound
21,
22 and
23 showed excellent activity against
C. albicans with MIC-10 μg/ml. Out of the above-mentioned compounds,
22 and
23 also showed good activity against
S. aureus with MIC-20 and 15 μg/ml respectively. |
| doi_str_mv | 10.1016/j.ejmech.2005.03.012 |
| format | Article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_68808458</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0223523405001005</els_id><sourcerecordid>68808458</sourcerecordid><originalsourceid>FETCH-LOGICAL-c390t-6379b8d7a4837d1852b1a384fe766180b012cd618ba7ab1c3a9ce4474adbdc303</originalsourceid><addsrcrecordid>eNp9kMtqGzEUQEVISZykf1DKbBJSqKZ6zUjOohBCXxDIou1a6HFdy4wlVxqHzt9XUxuy6-oK3XNfB6E3lLSU0P7DpoXNFty6ZYR0LeEtoewELajsFeasE6doQRjjuGNcnKOLUjakgj0hZ-icdkoqRpcLpBm-z9MQPETAAt8KvFtDTH-mf3Ea3tn9iDmGWJNpxspd832K4xpKKO-bDMaNIcXSmOgbG9KQfgVnhmb-fg7jdIVercxQ4PUxXqKfnz_9ePiKH5--fHu4f8SOL8mIey6XVnlphOLSU9UxSw1XYgWy76kith7nfH1ZI42ljpulAyGkMN56xwm_RDeHvrucfu-hjHobioNhMBHSvuheKaJEpyooDqDLqZQMK73LYWvypCnRs1i90QexeharCdd1di17e-y_t1vwL0VHkxW4PgKmVAGrbKIL5YWTXPaCzvM_HjioNp4DZF1cgOjAhwxu1D6F_2_yF7EVl1Y</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>68808458</pqid></control><display><type>article</type><title>2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity</title><source>MEDLINE</source><source>Access via ScienceDirect (Elsevier)</source><creator>Husain, Asif ; Khan, M.S.Y. ; Hasan, S.M. ; Alam, M.M.</creator><creatorcontrib>Husain, Asif ; Khan, M.S.Y. ; Hasan, S.M. ; Alam, M.M.</creatorcontrib><description>2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (
1–
17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxy-phenyl)-2(3
H)-pyrrolones (
18–
23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3
H)-pyrrolones (
24–
29) respectively, which were characterized on the basis of
1H-,
13C-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for anti-inflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (
5,
6,
7,
25 and
26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against
Staphylococcus aureus and
Escherichia coli as well as antifungal activity against
Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound
21,
22 and
23 showed excellent activity against
C. albicans with MIC-10 μg/ml. Out of the above-mentioned compounds,
22 and
23 also showed good activity against
S. aureus with MIC-20 and 15 μg/ml respectively.</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2005.03.012</identifier><identifier>PMID: 15878219</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Oxford: Elsevier Masson SAS</publisher><subject>Analgesic ; Analgesics ; Animals ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - chemistry ; Anti-Bacterial Agents - pharmacology ; Anti-inflammatory ; Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis ; Anti-Inflammatory Agents, Non-Steroidal - chemistry ; Anti-Inflammatory Agents, Non-Steroidal - pharmacology ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Antifungal Agents - chemical synthesis ; Antifungal Agents - chemistry ; Antifungal Agents - pharmacology ; Antimicrobial activity ; Aroylpropionic acid ; Bacteria - drug effects ; Biological and medical sciences ; Biphenyl Compounds - chemical synthesis ; Biphenyl Compounds - chemistry ; Biphenyl Compounds - pharmacology ; Bones, joints and connective tissue. Antiinflammatory agents ; Butenolide ; Dose-Response Relationship, Drug ; Fungi - drug effects ; General aspects ; Medical sciences ; Mice ; Microbial Sensitivity Tests ; Molecular Structure ; Neuropharmacology ; Pain Measurement - drug effects ; Pharmacology. Drug treatments ; Pyrrolone ; Rats ; Structure-Activity Relationship ; Ulcerogenic</subject><ispartof>European journal of medicinal chemistry, 2005-12, Vol.40 (12), p.1394-1404</ispartof><rights>2005 Elsevier SAS</rights><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c390t-6379b8d7a4837d1852b1a384fe766180b012cd618ba7ab1c3a9ce4474adbdc303</citedby><cites>FETCH-LOGICAL-c390t-6379b8d7a4837d1852b1a384fe766180b012cd618ba7ab1c3a9ce4474adbdc303</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/j.ejmech.2005.03.012$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17376418$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/15878219$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Husain, Asif</creatorcontrib><creatorcontrib>Khan, M.S.Y.</creatorcontrib><creatorcontrib>Hasan, S.M.</creatorcontrib><creatorcontrib>Alam, M.M.</creatorcontrib><title>2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (
1–
17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxy-phenyl)-2(3
H)-pyrrolones (
18–
23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3
H)-pyrrolones (
24–
29) respectively, which were characterized on the basis of
1H-,
13C-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for anti-inflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (
5,
6,
7,
25 and
26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against
Staphylococcus aureus and
Escherichia coli as well as antifungal activity against
Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound
21,
22 and
23 showed excellent activity against
C. albicans with MIC-10 μg/ml. Out of the above-mentioned compounds,
22 and
23 also showed good activity against
S. aureus with MIC-20 and 15 μg/ml respectively.</description><subject>Analgesic</subject><subject>Analgesics</subject><subject>Animals</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - chemistry</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Anti-inflammatory</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - chemistry</subject><subject>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Antifungal Agents - chemical synthesis</subject><subject>Antifungal Agents - chemistry</subject><subject>Antifungal Agents - pharmacology</subject><subject>Antimicrobial activity</subject><subject>Aroylpropionic acid</subject><subject>Bacteria - drug effects</subject><subject>Biological and medical sciences</subject><subject>Biphenyl Compounds - chemical synthesis</subject><subject>Biphenyl Compounds - chemistry</subject><subject>Biphenyl Compounds - pharmacology</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Butenolide</subject><subject>Dose-Response Relationship, Drug</subject><subject>Fungi - drug effects</subject><subject>General aspects</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Microbial Sensitivity Tests</subject><subject>Molecular Structure</subject><subject>Neuropharmacology</subject><subject>Pain Measurement - drug effects</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrrolone</subject><subject>Rats</subject><subject>Structure-Activity Relationship</subject><subject>Ulcerogenic</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2005</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNp9kMtqGzEUQEVISZykf1DKbBJSqKZ6zUjOohBCXxDIou1a6HFdy4wlVxqHzt9XUxuy6-oK3XNfB6E3lLSU0P7DpoXNFty6ZYR0LeEtoewELajsFeasE6doQRjjuGNcnKOLUjakgj0hZ-icdkoqRpcLpBm-z9MQPETAAt8KvFtDTH-mf3Ea3tn9iDmGWJNpxspd832K4xpKKO-bDMaNIcXSmOgbG9KQfgVnhmb-fg7jdIVercxQ4PUxXqKfnz_9ePiKH5--fHu4f8SOL8mIey6XVnlphOLSU9UxSw1XYgWy76kith7nfH1ZI42ljpulAyGkMN56xwm_RDeHvrucfu-hjHobioNhMBHSvuheKaJEpyooDqDLqZQMK73LYWvypCnRs1i90QexeharCdd1di17e-y_t1vwL0VHkxW4PgKmVAGrbKIL5YWTXPaCzvM_HjioNp4DZF1cgOjAhwxu1D6F_2_yF7EVl1Y</recordid><startdate>20051201</startdate><enddate>20051201</enddate><creator>Husain, Asif</creator><creator>Khan, M.S.Y.</creator><creator>Hasan, S.M.</creator><creator>Alam, M.M.</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>20051201</creationdate><title>2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity</title><author>Husain, Asif ; Khan, M.S.Y. ; Hasan, S.M. ; Alam, M.M.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c390t-6379b8d7a4837d1852b1a384fe766180b012cd618ba7ab1c3a9ce4474adbdc303</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2005</creationdate><topic>Analgesic</topic><topic>Analgesics</topic><topic>Animals</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - chemistry</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Anti-inflammatory</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - chemistry</topic><topic>Anti-Inflammatory Agents, Non-Steroidal - pharmacology</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Antifungal Agents - chemical synthesis</topic><topic>Antifungal Agents - chemistry</topic><topic>Antifungal Agents - pharmacology</topic><topic>Antimicrobial activity</topic><topic>Aroylpropionic acid</topic><topic>Bacteria - drug effects</topic><topic>Biological and medical sciences</topic><topic>Biphenyl Compounds - chemical synthesis</topic><topic>Biphenyl Compounds - chemistry</topic><topic>Biphenyl Compounds - pharmacology</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Butenolide</topic><topic>Dose-Response Relationship, Drug</topic><topic>Fungi - drug effects</topic><topic>General aspects</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Microbial Sensitivity Tests</topic><topic>Molecular Structure</topic><topic>Neuropharmacology</topic><topic>Pain Measurement - drug effects</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrrolone</topic><topic>Rats</topic><topic>Structure-Activity Relationship</topic><topic>Ulcerogenic</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Husain, Asif</creatorcontrib><creatorcontrib>Khan, M.S.Y.</creatorcontrib><creatorcontrib>Hasan, S.M.</creatorcontrib><creatorcontrib>Alam, M.M.</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>Husain, Asif</au><au>Khan, M.S.Y.</au><au>Hasan, S.M.</au><au>Alam, M.M.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2005-12-01</date><risdate>2005</risdate><volume>40</volume><issue>12</issue><spage>1394</spage><epage>1404</epage><pages>1394-1404</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides (
1–
17) were prepared from 3-(4-phenoxy-benzoyl)propionic acid and aromatic aldehydes. Some of the selected butenolides were reacted with ammonia and benzylamine to give corresponding 3-arylidene-5-(4-phenoxy-phenyl)-2(3
H)-pyrrolones (
18–
23) and 3-arylidene-5-(4-phenoxy-phenyl)-1-benzyl-2(3
H)-pyrrolones (
24–
29) respectively, which were characterized on the basis of
1H-,
13C-NMR, Mass spectrometric data and elemental analysis results. These compounds were tested for anti-inflammatory and antimicrobial actions. The compounds, which showed significant anti-inflammatory activity, were screened for their analgesic and ulcerogenic activities. Five new compounds (
5,
6,
7,
25 and
26), out of 29 showed very good anti-inflammatory activity in the carrageenan induced rat paw edema test, with significant analgesic activity in the acetic acid induced writhing test together with negligible ulcerogenic action. Antibacterial activity against
Staphylococcus aureus and
Escherichia coli as well as antifungal activity against
Candida albicans were expressed as the corresponding minimum inhibitory concentration (MIC) values. Compound
21,
22 and
23 showed excellent activity against
C. albicans with MIC-10 μg/ml. Out of the above-mentioned compounds,
22 and
23 also showed good activity against
S. aureus with MIC-20 and 15 μg/ml respectively.</abstract><cop>Oxford</cop><pub>Elsevier Masson SAS</pub><pmid>15878219</pmid><doi>10.1016/j.ejmech.2005.03.012</doi><tpages>11</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2005-12, Vol.40 (12), p.1394-1404 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_68808458 |
| source | MEDLINE; Access via ScienceDirect (Elsevier) |
| subjects | Analgesic Analgesics Animals Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - chemistry Anti-Bacterial Agents - pharmacology Anti-inflammatory Anti-Inflammatory Agents, Non-Steroidal - chemical synthesis Anti-Inflammatory Agents, Non-Steroidal - chemistry Anti-Inflammatory Agents, Non-Steroidal - pharmacology Antibiotics. Antiinfectious agents. Antiparasitic agents Antifungal Agents - chemical synthesis Antifungal Agents - chemistry Antifungal Agents - pharmacology Antimicrobial activity Aroylpropionic acid Bacteria - drug effects Biological and medical sciences Biphenyl Compounds - chemical synthesis Biphenyl Compounds - chemistry Biphenyl Compounds - pharmacology Bones, joints and connective tissue. Antiinflammatory agents Butenolide Dose-Response Relationship, Drug Fungi - drug effects General aspects Medical sciences Mice Microbial Sensitivity Tests Molecular Structure Neuropharmacology Pain Measurement - drug effects Pharmacology. Drug treatments Pyrrolone Rats Structure-Activity Relationship Ulcerogenic |
| title | 2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides: Synthesis, reactions and biological activity |
| url | https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2024-12-29T13%3A27%3A57IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=2-Arylidene-4-(4-phenoxy-phenyl)but-3-en-4-olides:%20Synthesis,%20reactions%20and%20biological%20activity&rft.jtitle=European%20journal%20of%20medicinal%20chemistry&rft.au=Husain,%20Asif&rft.date=2005-12-01&rft.volume=40&rft.issue=12&rft.spage=1394&rft.epage=1404&rft.pages=1394-1404&rft.issn=0223-5234&rft.eissn=1768-3254&rft.coden=EJMCA5&rft_id=info:doi/10.1016/j.ejmech.2005.03.012&rft_dat=%3Cproquest_cross%3E68808458%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=68808458&rft_id=info:pmid/15878219&rft_els_id=S0223523405001005&rfr_iscdi=true |