Semisynthetic Derivatives of Madurahydroxylactone and Their Antibacterial Activities
Madurahydroxylactone is a secondary metabolite from Nonomuria rubra (former Actinomadura rubra) with in vitro activity against Gram-positive bacteria and belongs to the family of benzo[a]naphthacenequinones. A series of derivatives of madurahydroxylactone were synthesized to investigate the effect o...
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| Veröffentlicht in: | Journal of antibiotics 1999/11/25, Vol.52(11), pp.1029-1041 |
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| container_end_page | 1041 |
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| container_issue | 11 |
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| container_title | Journal of antibiotics |
| container_volume | 52 |
| creator | HEINISCH, LOTHAR ROEMER, ERNST JÜTTEN, PETER HAAS, WOLFGANG WERNER, WALTER MÖLLMANN, UTE |
| description | Madurahydroxylactone is a secondary metabolite from Nonomuria rubra (former Actinomadura rubra) with in vitro activity against Gram-positive bacteria and belongs to the family of benzo[a]naphthacenequinones. A series of derivatives of madurahydroxylactone were synthesized to investigate the effect on the antibacterial activity. Reaction with alcohols and amines gave cyclic acetals or aminals derived from the lactone form, whereas other amino reagents like hydroxylarnines and acyl or sulfonyl hydrazides led to the corresponding imine derivatives of the aldehyde. Hydrazine, alkyl and aryl hydrazines react with madurahydroxylactone under cyclization to give compounds of the new heterocyclic basic structure naphthaceno[1, 2-g]phthalazine. Some new compounds strongly inhibit Gram-positive bacteria, in part stronger than the parent compound. |
| doi_str_mv | 10.7164/antibiotics.52.1029 |
| format | Article |
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A series of derivatives of madurahydroxylactone were synthesized to investigate the effect on the antibacterial activity. Reaction with alcohols and amines gave cyclic acetals or aminals derived from the lactone form, whereas other amino reagents like hydroxylarnines and acyl or sulfonyl hydrazides led to the corresponding imine derivatives of the aldehyde. Hydrazine, alkyl and aryl hydrazines react with madurahydroxylactone under cyclization to give compounds of the new heterocyclic basic structure naphthaceno[1, 2-g]phthalazine. Some new compounds strongly inhibit Gram-positive bacteria, in part stronger than the parent compound.</description><identifier>ISSN: 0021-8820</identifier><identifier>EISSN: 1881-1469</identifier><identifier>DOI: 10.7164/antibiotics.52.1029</identifier><identifier>PMID: 10656576</identifier><identifier>CODEN: JANTAJ</identifier><language>eng</language><publisher>Tokyo: JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</publisher><subject>Actinomadura rubra ; Actinomycetales - metabolism ; Anti-Bacterial Agents - chemical synthesis ; Anti-Bacterial Agents - pharmacology ; Antibacterial agents ; Antibiotics. Antiinfectious agents. Antiparasitic agents ; Biological and medical sciences ; Gram-Positive Bacteria - drug effects ; madurahydroxylactone ; Medical sciences ; Nonomuria rubra ; Pharmacology. Drug treatments ; Quinones - pharmacology ; Structure-Activity Relationship</subject><ispartof>The Journal of Antibiotics, 1999/11/25, Vol.52(11), pp.1029-1041</ispartof><rights>Japan Antibiotics Research Association</rights><rights>2000 INIST-CNRS</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c572t-9f8caa4607402499e3cdd95966599bbf47aee4b940ca81a0dcf7fe42bb00dcc73</citedby></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,1877,27901,27902</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=1318101$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/10656576$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>HEINISCH, LOTHAR</creatorcontrib><creatorcontrib>ROEMER, ERNST</creatorcontrib><creatorcontrib>JÜTTEN, PETER</creatorcontrib><creatorcontrib>HAAS, WOLFGANG</creatorcontrib><creatorcontrib>WERNER, WALTER</creatorcontrib><creatorcontrib>MÖLLMANN, UTE</creatorcontrib><title>Semisynthetic Derivatives of Madurahydroxylactone and Their Antibacterial Activities</title><title>Journal of antibiotics</title><addtitle>J. Antibiot.</addtitle><description>Madurahydroxylactone is a secondary metabolite from Nonomuria rubra (former Actinomadura rubra) with in vitro activity against Gram-positive bacteria and belongs to the family of benzo[a]naphthacenequinones. A series of derivatives of madurahydroxylactone were synthesized to investigate the effect on the antibacterial activity. Reaction with alcohols and amines gave cyclic acetals or aminals derived from the lactone form, whereas other amino reagents like hydroxylarnines and acyl or sulfonyl hydrazides led to the corresponding imine derivatives of the aldehyde. Hydrazine, alkyl and aryl hydrazines react with madurahydroxylactone under cyclization to give compounds of the new heterocyclic basic structure naphthaceno[1, 2-g]phthalazine. Some new compounds strongly inhibit Gram-positive bacteria, in part stronger than the parent compound.</description><subject>Actinomadura rubra</subject><subject>Actinomycetales - metabolism</subject><subject>Anti-Bacterial Agents - chemical synthesis</subject><subject>Anti-Bacterial Agents - pharmacology</subject><subject>Antibacterial agents</subject><subject>Antibiotics. Antiinfectious agents. Antiparasitic agents</subject><subject>Biological and medical sciences</subject><subject>Gram-Positive Bacteria - drug effects</subject><subject>madurahydroxylactone</subject><subject>Medical sciences</subject><subject>Nonomuria rubra</subject><subject>Pharmacology. Drug treatments</subject><subject>Quinones - pharmacology</subject><subject>Structure-Activity Relationship</subject><issn>0021-8820</issn><issn>1881-1469</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1999</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkEtvEzEUhS0EoqHwC5DQLBC7Cb5jjx_LqDyKVGBBWFt3PHeIq8lMsZ2q-fc4JCrZsbEt-zvnXB_GXgNfalDyPU45dGHOwadl2yyBN_YJW4AxUINU9ilbcN5AbUzDL9iLlG45F1po85xdAFetarVasPUP2oa0n_KGilH1gWK4xxzuKVXzUH3Ffhdxs-_j_LAf0ed5ogqnvlpvKMRqdZig3BYRjtXKF13IgdJL9mzAMdGr037Jfn76uL66rm--f_5ytbqpfaubXNvBeESpuJa8kdaS8H1vW6tUa23XDVIjkeys5B4NIO_9oAeSTdfxcvZaXLJ3R9-7OP_eUcqu_MXTOOJE8y45ZSW0QvwfBC2NkFoWUBxBH-eUIg3uLoYtxr0D7g6tu7PWXdu4Q-tF9eZkv-u21J9pjjUX4O0JwORxHCJOPqR_nAADHAr27Yjdpoy_6PEdY4kb6TwbrDJ_8-G0HgZ5BP0Go6NJ_AFDYKuz</recordid><startdate>19991101</startdate><enddate>19991101</enddate><creator>HEINISCH, LOTHAR</creator><creator>ROEMER, ERNST</creator><creator>JÜTTEN, PETER</creator><creator>HAAS, WOLFGANG</creator><creator>WERNER, WALTER</creator><creator>MÖLLMANN, UTE</creator><general>JAPAN ANTIBIOTICS RESEARCH ASSOCIATION</general><general>Japan Antibiotics Research Association</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>7T7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope></search><sort><creationdate>19991101</creationdate><title>Semisynthetic Derivatives of Madurahydroxylactone and Their Antibacterial Activities</title><author>HEINISCH, LOTHAR ; ROEMER, ERNST ; JÜTTEN, PETER ; HAAS, WOLFGANG ; WERNER, WALTER ; MÖLLMANN, UTE</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c572t-9f8caa4607402499e3cdd95966599bbf47aee4b940ca81a0dcf7fe42bb00dcc73</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1999</creationdate><topic>Actinomadura rubra</topic><topic>Actinomycetales - metabolism</topic><topic>Anti-Bacterial Agents - chemical synthesis</topic><topic>Anti-Bacterial Agents - pharmacology</topic><topic>Antibacterial agents</topic><topic>Antibiotics. Antiinfectious agents. Antiparasitic agents</topic><topic>Biological and medical sciences</topic><topic>Gram-Positive Bacteria - drug effects</topic><topic>madurahydroxylactone</topic><topic>Medical sciences</topic><topic>Nonomuria rubra</topic><topic>Pharmacology. 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Antibiot.</addtitle><date>1999-11-01</date><risdate>1999</risdate><volume>52</volume><issue>11</issue><spage>1029</spage><epage>1041</epage><pages>1029-1041</pages><issn>0021-8820</issn><eissn>1881-1469</eissn><coden>JANTAJ</coden><abstract>Madurahydroxylactone is a secondary metabolite from Nonomuria rubra (former Actinomadura rubra) with in vitro activity against Gram-positive bacteria and belongs to the family of benzo[a]naphthacenequinones. A series of derivatives of madurahydroxylactone were synthesized to investigate the effect on the antibacterial activity. Reaction with alcohols and amines gave cyclic acetals or aminals derived from the lactone form, whereas other amino reagents like hydroxylarnines and acyl or sulfonyl hydrazides led to the corresponding imine derivatives of the aldehyde. Hydrazine, alkyl and aryl hydrazines react with madurahydroxylactone under cyclization to give compounds of the new heterocyclic basic structure naphthaceno[1, 2-g]phthalazine. 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| fulltext | fulltext |
| identifier | ISSN: 0021-8820 |
| ispartof | The Journal of Antibiotics, 1999/11/25, Vol.52(11), pp.1029-1041 |
| issn | 0021-8820 1881-1469 |
| language | eng |
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| subjects | Actinomadura rubra Actinomycetales - metabolism Anti-Bacterial Agents - chemical synthesis Anti-Bacterial Agents - pharmacology Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Gram-Positive Bacteria - drug effects madurahydroxylactone Medical sciences Nonomuria rubra Pharmacology. Drug treatments Quinones - pharmacology Structure-Activity Relationship |
| title | Semisynthetic Derivatives of Madurahydroxylactone and Their Antibacterial Activities |
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