Syntheses of Novel Isopenam and Isocephem Antibiotics. Preparation of a retinamido derivative of a highly strained β-lactam as potent anticancer agent
Syntheses of the cis‐configurated isopenam 9 (Scheme 1), isocephem 14 (Scheme 2), and isocephem 19 (Scheme 3) are described. The key step in the preparation of 14 and 19 involved a Pummerer‐type rearrangement of the corresponding sulfoxides 12 and 18. These β‐lactams were found to possess biological...
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| Veröffentlicht in: | Helvetica chimica acta 1992-10, Vol.75 (6), p.1840-1847 |
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| container_title | Helvetica chimica acta |
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| creator | Hakimelahi, Gholam H. Shiao, Min-Jen Hwu, Jih Ru Davari, Hady |
| description | Syntheses of the cis‐configurated isopenam 9 (Scheme 1), isocephem 14 (Scheme 2), and isocephem 19 (Scheme 3) are described. The key step in the preparation of 14 and 19 involved a Pummerer‐type rearrangement of the corresponding sulfoxides 12 and 18. These β‐lactams were found to possess biological activity against several pathogenic microorganisms in vitro. The electronic activation of the lactam moiety of 19 remarkably enhanced its biological activity. A retinoic moiety was attached to 19 via an amino linker. The resultant retinamido‐β‐lactam 21 showed significant cytostatic activity in tracheal organ cultures obtained from vitamin‐A‐deficient hamsters. |
| doi_str_mv | 10.1002/hlca.19920750610 |
| format | Article |
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Preparation of a retinamido derivative of a highly strained β-lactam as potent anticancer agent</title><source>Wiley Online Library Journals Frontfile Complete</source><creator>Hakimelahi, Gholam H. ; Shiao, Min-Jen ; Hwu, Jih Ru ; Davari, Hady</creator><creatorcontrib>Hakimelahi, Gholam H. ; Shiao, Min-Jen ; Hwu, Jih Ru ; Davari, Hady</creatorcontrib><description>Syntheses of the cis‐configurated isopenam 9 (Scheme 1), isocephem 14 (Scheme 2), and isocephem 19 (Scheme 3) are described. The key step in the preparation of 14 and 19 involved a Pummerer‐type rearrangement of the corresponding sulfoxides 12 and 18. These β‐lactams were found to possess biological activity against several pathogenic microorganisms in vitro. The electronic activation of the lactam moiety of 19 remarkably enhanced its biological activity. A retinoic moiety was attached to 19 via an amino linker. The resultant retinamido‐β‐lactam 21 showed significant cytostatic activity in tracheal organ cultures obtained from vitamin‐A‐deficient hamsters.</description><identifier>ISSN: 0018-019X</identifier><identifier>EISSN: 1522-2675</identifier><identifier>DOI: 10.1002/hlca.19920750610</identifier><identifier>CODEN: HCACAV</identifier><language>eng</language><publisher>Weinheim: WILEY-VCH Verlag GmbH</publisher><subject>Chemistry ; Exact sciences and technology ; Heterocyclic compounds ; Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms ; Organic chemistry ; Preparations and properties</subject><ispartof>Helvetica chimica acta, 1992-10, Vol.75 (6), p.1840-1847</ispartof><rights>Copyright © 1992 Verlag GmbH & Co. KGaA, Weinheim</rights><rights>1992 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3620-ad5ced94a125f77346f33ab8d1a76593057b2762fd954927f3de6f0cbfe9d48a3</citedby><cites>FETCH-LOGICAL-c3620-ad5ced94a125f77346f33ab8d1a76593057b2762fd954927f3de6f0cbfe9d48a3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fhlca.19920750610$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fhlca.19920750610$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=5569160$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Hakimelahi, Gholam H.</creatorcontrib><creatorcontrib>Shiao, Min-Jen</creatorcontrib><creatorcontrib>Hwu, Jih Ru</creatorcontrib><creatorcontrib>Davari, Hady</creatorcontrib><title>Syntheses of Novel Isopenam and Isocephem Antibiotics. 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The resultant retinamido‐β‐lactam 21 showed significant cytostatic activity in tracheal organ cultures obtained from vitamin‐A‐deficient hamsters.</description><subject>Chemistry</subject><subject>Exact sciences and technology</subject><subject>Heterocyclic compounds</subject><subject>Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms</subject><subject>Organic chemistry</subject><subject>Preparations and properties</subject><issn>0018-019X</issn><issn>1522-2675</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1992</creationdate><recordtype>article</recordtype><recordid>eNqFkM1uEzEUhUcIJEJhz9ILthNsT2zHCxYhtE2lqCC1qBUb68a-7hgmMyPbCuRJeA8epM_UGQ2qYNXV1f35zrk6RfGW0TmjlL-vGwtzpjWnSlDJ6LNixgTnJZdKPC9mlLJlSZm-fVm8Suk7pVRrqmbF76tjm2tMmEjnyWV3wIZcpK7HFvYEWjc2Fvsa92TV5rALXQ42zcmXiD1EyKFrRxBIxBwGJriOOIzhMKwOOK3qcFc3R5JyhNCiI_d_ygZsHg0S6buMbR6sBl1oLUYCd8PgdfHCQ5Pwzd96Unw9O71eb8rt5_OL9Wpb2kpyWoITFp1eAOPCK1UtpK8q2C0dAyWFrqhQO64k906LhebKVw6lp3bnUbvFEqqTgk66NnYpRfSmj2EP8WgYNWOwZgzW_BPsgLybkB6ShcbH4e2QHjkhpGZyPPswnf0MDR6flDWb7Xr1v0058SFl_PXIQ_xhpKqUMDeX50awj5uzb1efzLZ6AKHinc4</recordid><startdate>19921002</startdate><enddate>19921002</enddate><creator>Hakimelahi, Gholam H.</creator><creator>Shiao, Min-Jen</creator><creator>Hwu, Jih Ru</creator><creator>Davari, Hady</creator><general>WILEY-VCH Verlag GmbH</general><general>WILEY‐VCH Verlag GmbH</general><general>Wiley</general><scope>BSCLL</scope><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope></search><sort><creationdate>19921002</creationdate><title>Syntheses of Novel Isopenam and Isocephem Antibiotics. 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Preparation of a retinamido derivative of a highly strained β-lactam as potent anticancer agent</atitle><jtitle>Helvetica chimica acta</jtitle><addtitle>HCA</addtitle><date>1992-10-02</date><risdate>1992</risdate><volume>75</volume><issue>6</issue><spage>1840</spage><epage>1847</epage><pages>1840-1847</pages><issn>0018-019X</issn><eissn>1522-2675</eissn><coden>HCACAV</coden><abstract>Syntheses of the cis‐configurated isopenam 9 (Scheme 1), isocephem 14 (Scheme 2), and isocephem 19 (Scheme 3) are described. The key step in the preparation of 14 and 19 involved a Pummerer‐type rearrangement of the corresponding sulfoxides 12 and 18. These β‐lactams were found to possess biological activity against several pathogenic microorganisms in vitro. The electronic activation of the lactam moiety of 19 remarkably enhanced its biological activity. A retinoic moiety was attached to 19 via an amino linker. The resultant retinamido‐β‐lactam 21 showed significant cytostatic activity in tracheal organ cultures obtained from vitamin‐A‐deficient hamsters.</abstract><cop>Weinheim</cop><pub>WILEY-VCH Verlag GmbH</pub><doi>10.1002/hlca.19920750610</doi><tpages>8</tpages></addata></record> |
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| identifier | ISSN: 0018-019X |
| ispartof | Helvetica chimica acta, 1992-10, Vol.75 (6), p.1840-1847 |
| issn | 0018-019X 1522-2675 |
| language | eng |
| recordid | cdi_crossref_primary_10_1002_hlca_19920750610 |
| source | Wiley Online Library Journals Frontfile Complete |
| subjects | Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry Preparations and properties |
| title | Syntheses of Novel Isopenam and Isocephem Antibiotics. Preparation of a retinamido derivative of a highly strained β-lactam as potent anticancer agent |
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