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Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines
Novel series of bicyclic pyrrolo[1,2-c]pyrimidines 3a– g, 5, 6a, b, and 7a, b, tricyclic pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines 8a– c, 9a– g, 13a– c, 17, 18a, b, 19, 20a, b and 21 and tetracyclic condensed pyrimidines 14, 22 and 23 were synthesized through different chemical reactions. Structures...
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| Published in: | European journal of medicinal chemistry 2009-11, Vol.44 (11), p.4572-4584 |
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| Main Authors: | , , , |
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| container_end_page | 4584 |
| container_issue | 11 |
| container_start_page | 4572 |
| container_title | European journal of medicinal chemistry |
| container_volume | 44 |
| creator | Amin, Kamilia M. Hanna, Mona M. Abo-Youssef, Hanan E. George, Riham F. |
| description | Novel series of bicyclic pyrrolo[1,2-c]pyrimidines
3a–
g,
5,
6a,
b, and
7a,
b, tricyclic pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines
8a–
c,
9a–
g,
13a–
c,
17,
18a,
b,
19,
20a,
b and
21 and tetracyclic condensed pyrimidines
14,
22 and
23 were synthesized through different chemical reactions. Structures of all synthesized pyrimidine derivatives were supported by spectral and elemental analyses. Analgesic activity evaluation was carried out using acetic acid-induced writhing assay, and all compounds exerted comparable activity to indomethacin. The anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema in rats, the potency of the bicyclic derivatives
3a–
f and
7b revealed comparable activity to indomethacin without gastric ulceration. The tricyclic derivatives
13a and
20a exerted good activity, however, they induced gastric ulcers while
13b and
13c showed moderate activity without ulceration. In case of tetracyclic derivatives, compound
14 exhibited the highest potency and safety profile.
[Display omitted] |
| doi_str_mv | 10.1016/j.ejmech.2009.06.028 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_734079100</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0223523409003523</els_id><sourcerecordid>734079100</sourcerecordid><originalsourceid>FETCH-LOGICAL-c391t-3ae3181184121bd8ddc9e1dad6e88b562962013b3130f836adc743101e7bfcb63</originalsourceid><addsrcrecordid>eNp9kMFu1DAQhi0EotvCGyCUC-LShBk76zgXpKqigFSJA3C2HHtCvUqcxfauyNvjsiu4cRh5Dt8_nvkYe4XQIKB8t2toN5N9aDhA34BsgKsnbIOdVLXg2_Yp2wDnot5y0V6wy5R2ALCVAM_ZBfaSK4GwYb--riE_UPLpujLBTD9Ka0vnSmVf-zBOZp5NXuJaGZv90WdPqaKjmQ4m-yVUy1ilZaZq8PV1laOv_6Qz5WjsaqcyzS7BUUjkqv0a_eydD5ResGejmRK9PL9X7Pvdh2-3n-r7Lx8_397c11b0mGthSKBCVC1yHJxyzvaEzjhJSg1bycslgGIQKGBUQhpnu7ZchtQNox2kuGJvT3P3cfl5oJT17JOlaTKBlkPSnWih6xGgkO2JtHFJKdKo92VbE1eNoB-V650-KdePyjVIXZSX2OvzB4dhJvcvdHZcgDdnwCRrpjGaYH36y3GOvC1VuPcnjoqOo6eok_UULDkfyWbtFv__TX4D1suiaA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>734079100</pqid></control><display><type>article</type><title>Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines</title><source>ScienceDirect Journals</source><creator>Amin, Kamilia M. ; Hanna, Mona M. ; Abo-Youssef, Hanan E. ; George, Riham F.</creator><creatorcontrib>Amin, Kamilia M. ; Hanna, Mona M. ; Abo-Youssef, Hanan E. ; George, Riham F.</creatorcontrib><description>Novel series of bicyclic pyrrolo[1,2-c]pyrimidines
3a–
g,
5,
6a,
b, and
7a,
b, tricyclic pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines
8a–
c,
9a–
g,
13a–
c,
17,
18a,
b,
19,
20a,
b and
21 and tetracyclic condensed pyrimidines
14,
22 and
23 were synthesized through different chemical reactions. Structures of all synthesized pyrimidine derivatives were supported by spectral and elemental analyses. Analgesic activity evaluation was carried out using acetic acid-induced writhing assay, and all compounds exerted comparable activity to indomethacin. The anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema in rats, the potency of the bicyclic derivatives
3a–
f and
7b revealed comparable activity to indomethacin without gastric ulceration. The tricyclic derivatives
13a and
20a exerted good activity, however, they induced gastric ulcers while
13b and
13c showed moderate activity without ulceration. In case of tetracyclic derivatives, compound
14 exhibited the highest potency and safety profile.
[Display omitted]</description><identifier>ISSN: 0223-5234</identifier><identifier>EISSN: 1768-3254</identifier><identifier>DOI: 10.1016/j.ejmech.2009.06.028</identifier><identifier>PMID: 19628310</identifier><identifier>CODEN: EJMCA5</identifier><language>eng</language><publisher>Kidlington: Elsevier Masson SAS</publisher><subject>Analgesics ; Analgesics - adverse effects ; Analgesics - chemical synthesis ; Analgesics - chemistry ; Analgesics - therapeutic use ; Animals ; Anti-Inflammatory Agents - adverse effects ; Anti-Inflammatory Agents - chemical synthesis ; Anti-Inflammatory Agents - chemistry ; Anti-Inflammatory Agents - therapeutic use ; Anti-inflammatory and analgesic ; Biological and medical sciences ; Bones, joints and connective tissue. Antiinflammatory agents ; Condensed pyrimidines ; Crystallography, X-Ray ; Edema - chemically induced ; Edema - drug therapy ; Medical sciences ; Mice ; Models, Molecular ; Neuropharmacology ; Pain Measurement - drug effects ; Pharmacology. Drug treatments ; Pyrimidines - adverse effects ; Pyrimidines - chemical synthesis ; Pyrimidines - chemistry ; Pyrimidines - therapeutic use ; Pyrrolo[1,2-c]pyrimidines ; Rats ; Stomach - drug effects ; Stomach - pathology ; Tetracyclic pyrimidines ; Tricyclic pyrimidines ; Ulcer - etiology</subject><ispartof>European journal of medicinal chemistry, 2009-11, Vol.44 (11), p.4572-4584</ispartof><rights>2009 Elsevier Masson SAS</rights><rights>2015 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c391t-3ae3181184121bd8ddc9e1dad6e88b562962013b3130f836adc743101e7bfcb63</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=22124212$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/19628310$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Amin, Kamilia M.</creatorcontrib><creatorcontrib>Hanna, Mona M.</creatorcontrib><creatorcontrib>Abo-Youssef, Hanan E.</creatorcontrib><creatorcontrib>George, Riham F.</creatorcontrib><title>Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines</title><title>European journal of medicinal chemistry</title><addtitle>Eur J Med Chem</addtitle><description>Novel series of bicyclic pyrrolo[1,2-c]pyrimidines
3a–
g,
5,
6a,
b, and
7a,
b, tricyclic pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines
8a–
c,
9a–
g,
13a–
c,
17,
18a,
b,
19,
20a,
b and
21 and tetracyclic condensed pyrimidines
14,
22 and
23 were synthesized through different chemical reactions. Structures of all synthesized pyrimidine derivatives were supported by spectral and elemental analyses. Analgesic activity evaluation was carried out using acetic acid-induced writhing assay, and all compounds exerted comparable activity to indomethacin. The anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema in rats, the potency of the bicyclic derivatives
3a–
f and
7b revealed comparable activity to indomethacin without gastric ulceration. The tricyclic derivatives
13a and
20a exerted good activity, however, they induced gastric ulcers while
13b and
13c showed moderate activity without ulceration. In case of tetracyclic derivatives, compound
14 exhibited the highest potency and safety profile.
[Display omitted]</description><subject>Analgesics</subject><subject>Analgesics - adverse effects</subject><subject>Analgesics - chemical synthesis</subject><subject>Analgesics - chemistry</subject><subject>Analgesics - therapeutic use</subject><subject>Animals</subject><subject>Anti-Inflammatory Agents - adverse effects</subject><subject>Anti-Inflammatory Agents - chemical synthesis</subject><subject>Anti-Inflammatory Agents - chemistry</subject><subject>Anti-Inflammatory Agents - therapeutic use</subject><subject>Anti-inflammatory and analgesic</subject><subject>Biological and medical sciences</subject><subject>Bones, joints and connective tissue. Antiinflammatory agents</subject><subject>Condensed pyrimidines</subject><subject>Crystallography, X-Ray</subject><subject>Edema - chemically induced</subject><subject>Edema - drug therapy</subject><subject>Medical sciences</subject><subject>Mice</subject><subject>Models, Molecular</subject><subject>Neuropharmacology</subject><subject>Pain Measurement - drug effects</subject><subject>Pharmacology. Drug treatments</subject><subject>Pyrimidines - adverse effects</subject><subject>Pyrimidines - chemical synthesis</subject><subject>Pyrimidines - chemistry</subject><subject>Pyrimidines - therapeutic use</subject><subject>Pyrrolo[1,2-c]pyrimidines</subject><subject>Rats</subject><subject>Stomach - drug effects</subject><subject>Stomach - pathology</subject><subject>Tetracyclic pyrimidines</subject><subject>Tricyclic pyrimidines</subject><subject>Ulcer - etiology</subject><issn>0223-5234</issn><issn>1768-3254</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2009</creationdate><recordtype>article</recordtype><recordid>eNp9kMFu1DAQhi0EotvCGyCUC-LShBk76zgXpKqigFSJA3C2HHtCvUqcxfauyNvjsiu4cRh5Dt8_nvkYe4XQIKB8t2toN5N9aDhA34BsgKsnbIOdVLXg2_Yp2wDnot5y0V6wy5R2ALCVAM_ZBfaSK4GwYb--riE_UPLpujLBTD9Ka0vnSmVf-zBOZp5NXuJaGZv90WdPqaKjmQ4m-yVUy1ilZaZq8PV1laOv_6Qz5WjsaqcyzS7BUUjkqv0a_eydD5ResGejmRK9PL9X7Pvdh2-3n-r7Lx8_397c11b0mGthSKBCVC1yHJxyzvaEzjhJSg1bycslgGIQKGBUQhpnu7ZchtQNox2kuGJvT3P3cfl5oJT17JOlaTKBlkPSnWih6xGgkO2JtHFJKdKo92VbE1eNoB-V650-KdePyjVIXZSX2OvzB4dhJvcvdHZcgDdnwCRrpjGaYH36y3GOvC1VuPcnjoqOo6eok_UULDkfyWbtFv__TX4D1suiaA</recordid><startdate>20091101</startdate><enddate>20091101</enddate><creator>Amin, Kamilia M.</creator><creator>Hanna, Mona M.</creator><creator>Abo-Youssef, Hanan E.</creator><creator>George, Riham F.</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>20091101</creationdate><title>Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines</title><author>Amin, Kamilia M. ; Hanna, Mona M. ; Abo-Youssef, Hanan E. ; George, Riham F.</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c391t-3ae3181184121bd8ddc9e1dad6e88b562962013b3130f836adc743101e7bfcb63</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2009</creationdate><topic>Analgesics</topic><topic>Analgesics - adverse effects</topic><topic>Analgesics - chemical synthesis</topic><topic>Analgesics - chemistry</topic><topic>Analgesics - therapeutic use</topic><topic>Animals</topic><topic>Anti-Inflammatory Agents - adverse effects</topic><topic>Anti-Inflammatory Agents - chemical synthesis</topic><topic>Anti-Inflammatory Agents - chemistry</topic><topic>Anti-Inflammatory Agents - therapeutic use</topic><topic>Anti-inflammatory and analgesic</topic><topic>Biological and medical sciences</topic><topic>Bones, joints and connective tissue. Antiinflammatory agents</topic><topic>Condensed pyrimidines</topic><topic>Crystallography, X-Ray</topic><topic>Edema - chemically induced</topic><topic>Edema - drug therapy</topic><topic>Medical sciences</topic><topic>Mice</topic><topic>Models, Molecular</topic><topic>Neuropharmacology</topic><topic>Pain Measurement - drug effects</topic><topic>Pharmacology. Drug treatments</topic><topic>Pyrimidines - adverse effects</topic><topic>Pyrimidines - chemical synthesis</topic><topic>Pyrimidines - chemistry</topic><topic>Pyrimidines - therapeutic use</topic><topic>Pyrrolo[1,2-c]pyrimidines</topic><topic>Rats</topic><topic>Stomach - drug effects</topic><topic>Stomach - pathology</topic><topic>Tetracyclic pyrimidines</topic><topic>Tricyclic pyrimidines</topic><topic>Ulcer - etiology</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Amin, Kamilia M.</creatorcontrib><creatorcontrib>Hanna, Mona M.</creatorcontrib><creatorcontrib>Abo-Youssef, Hanan E.</creatorcontrib><creatorcontrib>George, Riham F.</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>Amin, Kamilia M.</au><au>Hanna, Mona M.</au><au>Abo-Youssef, Hanan E.</au><au>George, Riham F.</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines</atitle><jtitle>European journal of medicinal chemistry</jtitle><addtitle>Eur J Med Chem</addtitle><date>2009-11-01</date><risdate>2009</risdate><volume>44</volume><issue>11</issue><spage>4572</spage><epage>4584</epage><pages>4572-4584</pages><issn>0223-5234</issn><eissn>1768-3254</eissn><coden>EJMCA5</coden><abstract>Novel series of bicyclic pyrrolo[1,2-c]pyrimidines
3a–
g,
5,
6a,
b, and
7a,
b, tricyclic pyrimido[5,4-e]pyrrolo[1,2-c]pyrimidines
8a–
c,
9a–
g,
13a–
c,
17,
18a,
b,
19,
20a,
b and
21 and tetracyclic condensed pyrimidines
14,
22 and
23 were synthesized through different chemical reactions. Structures of all synthesized pyrimidine derivatives were supported by spectral and elemental analyses. Analgesic activity evaluation was carried out using acetic acid-induced writhing assay, and all compounds exerted comparable activity to indomethacin. The anti-inflammatory activity evaluation was performed using carrageenan-induced paw edema in rats, the potency of the bicyclic derivatives
3a–
f and
7b revealed comparable activity to indomethacin without gastric ulceration. The tricyclic derivatives
13a and
20a exerted good activity, however, they induced gastric ulcers while
13b and
13c showed moderate activity without ulceration. In case of tetracyclic derivatives, compound
14 exhibited the highest potency and safety profile.
[Display omitted]</abstract><cop>Kidlington</cop><pub>Elsevier Masson SAS</pub><pmid>19628310</pmid><doi>10.1016/j.ejmech.2009.06.028</doi><tpages>13</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0223-5234 |
| ispartof | European journal of medicinal chemistry, 2009-11, Vol.44 (11), p.4572-4584 |
| issn | 0223-5234 1768-3254 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_734079100 |
| source | ScienceDirect Journals |
| subjects | Analgesics Analgesics - adverse effects Analgesics - chemical synthesis Analgesics - chemistry Analgesics - therapeutic use Animals Anti-Inflammatory Agents - adverse effects Anti-Inflammatory Agents - chemical synthesis Anti-Inflammatory Agents - chemistry Anti-Inflammatory Agents - therapeutic use Anti-inflammatory and analgesic Biological and medical sciences Bones, joints and connective tissue. Antiinflammatory agents Condensed pyrimidines Crystallography, X-Ray Edema - chemically induced Edema - drug therapy Medical sciences Mice Models, Molecular Neuropharmacology Pain Measurement - drug effects Pharmacology. Drug treatments Pyrimidines - adverse effects Pyrimidines - chemical synthesis Pyrimidines - chemistry Pyrimidines - therapeutic use Pyrrolo[1,2-c]pyrimidines Rats Stomach - drug effects Stomach - pathology Tetracyclic pyrimidines Tricyclic pyrimidines Ulcer - etiology |
| title | Synthesis, analgesic and anti-inflammatory activities evaluation of some bi-, tri- and tetracyclic condensed pyrimidines |
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