Synthesis and Biological Properties of a Novel Cephalosporin FR86521 Having Potent Activity Against Methicillin-resistant Staphylococcus aureus (MRSA)
Recently, we introduced cefoselis (CFSL), which shows potent broad-spectrum activity against both Gram-positive bacteria, including MRSA, and Gram-negative bacteria, including P. aeruginosa. CFSL has a 7 beta -[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] side chain. We have focused recent e...
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| Published in | Journal of antibiotics Vol. 52; no. 12; pp. 1152 - 1155 |
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| Main Authors | , , , , , , , |
| Format | Journal Article |
| Language | English |
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TOKYO
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
1999
JAPAN ANTIBIOT RES ASSN Japan Antibiotics Research Association |
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| Abstract | Recently, we introduced cefoselis (CFSL), which shows potent broad-spectrum activity against both Gram-positive bacteria, including MRSA, and Gram-negative bacteria, including P. aeruginosa. CFSL has a 7 beta -[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] side chain. We have focused recent efforts on synthesizing novel cephalosporins superior to CFSL in antibacterial activity against both MRSA and P. aeruginosa, and as a result, we have discovered FR86521 (1) having a 7 beta -[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido] side chain. In this paper, we report the synthesis, and in vitro with 3 N hydrochloric acid in ethanol-acetone to produce FR86521 in 54.8% yield. The structure of FR86521 was confirmed by IR, super(1)H NMR, MS and elemental analysis. |
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| AbstractList | Recently, we introduced cefoselis (CFSL), which shows potent broad-spectrum activity against both Gram-positive bacteria, including MRSA, and Gram-negative bacteria, including P. aeruginosa. CFSL has a 7 beta -[(Z)-2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido] side chain. We have focused recent efforts on synthesizing novel cephalosporins superior to CFSL in antibacterial activity against both MRSA and P. aeruginosa, and as a result, we have discovered FR86521 (1) having a 7 beta -[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-ethoxyiminoacetamido] side chain. In this paper, we report the synthesis, and in vitro with 3 N hydrochloric acid in ethanol-acetone to produce FR86521 in 54.8% yield. The structure of FR86521 was confirmed by IR, super(1)H NMR, MS and elemental analysis. |
| Author | TAWARA, SHUICHI KISHI, KOHEI MATSUMOTO, SATORU OHKI, HIDENORI KAWABATA, KOHJI SAKANE, KAZUO MATSUMOTO, YOSHIMI OKUDA, SHINYA |
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| Keywords | ANTIBACTERIAL ACTIVITY FK037 SERIES Pseudomonadales Meticillin Penicillin derivatives Structure activity relation Bacteria Micrococcales Pseudomonadaceae Pseudomonas aeruginosa Micrococcaceae Chemical synthesis Staphylococcus aureus β-Lactams Rodentia In vitro Biological activity Infection Resistance In vivo Vertebrata Antibiotic Cephalosporin derivatives Mammalia Mouse Animal Minimum inhibitory concentration Bacteriosis Antibacterial agent |
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| References | 4) OHKI, H.; K. KAWABATA, S. OKUDA, T KAMIMURA & K. SAKANE: FK037, a new parenteral cephalosporin with a broad antibacterial spectrum: Synthesis and antibacterial activity. J. Antibiotics 46: 359-361, 1993 7) GOTO, I; K. SAKANE & T. TERAJI: Studies of 7β-[2-(aminoaryl)acetamido]cephalosporin derivatives. III. Synthesis and structure-activity relationships in the aminothiadiazole series. J. Antibiotics 37: 557-571, 1984 5) OHKI, H.; K. KAWABATA, Y INAMOTO, S. OKUDA, T. KAMIMURA & K. SAKANE: Studies on 3'-quaternary ammonium cephalosporins-IV Synthesis and antibacterial activity of 3'-(2-alkyl-3-aminopyrazolium)-cephalosporins related to FK037. Bioorg. Med. Chem. 5: 1685-1694, 1997 6) KISHI, K.; H. OHKI, S. OKUDA, K. KAWABATA, K. SAKANE & S. TAWARA: Structure-activity relationships and biological properties of a novel cephalosporin FR86521 having potent activity against methicillin-resistant Staphylococcus aureus (MRSA). Program and Abstracts of the 17th Symposium on Medicinal Chemistry, p. 64, Tsukuba,Nov. 19-21, 1997 1) LATTRELL, R.; J. BLUMBACH, W. DUERCKHEIMER, H.-W. FEHLHABER, K. FLEISCHMANN, R. KIRRSTETTER, B. MENCKE, K.-H. SCHEUNEMANN, E. SCHRINNER, W. SCHWAB, K. SEEGER, G. SEIBERT & M. WIEDUWILT: Synthesis and structure-activity relationships in the cefpirome series. I. 7-[2-(2-Aminothiazol-4-yl)-2-(Z)-oxyiminoacetamido]-3-[(substituted-1 -pyridinio)methyl] ceph-3-em-4-carboxylates. J. Antibiotics 41: 1374-1394, 1988 3) MIYAKE, A.; Y YOSHIMURA, M. YAMAOKA, T. NISHIMURA, N. HASHIMOTO & A. IMADA: Studies on condensedheterocyclic azolium cephalosporins. IV Synthesis and antibacterial activity of 7β-[2-(5-amino-l,2,4-thiadiazol3-yl)-2(Z)-alkoxyiminoacetamido]-3-(condensedheterocyclic azolium)methyl cephalosporins including SCE-2787. J. Antibiotics 45: 709-720, 1992 2) NAITO, T; S.. ABURAKI, H. KAMACHI, Y. NARITA, J. OKUMURA & H. KAWAGUCHI: Synthesis and structureactivity relationships of a new series of cephalosporins, BAY-28142 and related compounds. J. Antibiotics 39: 1092-1107,1986 LATTRELL, R (WOS:A1988Q643000009) 1988; 41 MIYAKE, A (WOS:A1992JB77400016) 1992; 45 KISHI K (WOS:000084428900013.2) 1997 NAITO, T (WOS:A1986D698000010) 1986; 39 GOTO, J (WOS:A1984SS85500018) 1984; 37 OHKI, H (WOS:A1993KN95800024) 1993; 46 Ohki, H (WOS:A1997XX51600019) 1997; 5 |
| References_xml | – volume: 41 start-page: 1374 year: 1988 ident: WOS:A1988Q643000009 article-title: SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS IN THE CEFPIROME SERIES .1. 7-[2-(2-AMINOTHIAZOL-4-YL)-2-(Z)-OXYIMINOACETAMIDO]-3-[(SUBSTITUTED-1-PYRIDINIO)METHYL]-CEPH-3-EM-4-CARBOXYLATES publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: LATTRELL, R – volume: 45 start-page: 709 year: 1992 ident: WOS:A1992JB77400016 article-title: STUDIES ON CONDENSED-HETEROCYCLIC AZOLIUM CEPHALOSPORINS .4. SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF 7-BETA-[2-(5-AMINO-1,2,4-THIADIAZOL-3-YL)-2(Z)-ALKOXYIMINOACETAMIDO]-3-(CONDENSED-HETEROCYCLIC AZOLIUM)METHYL CEPHALOSPORINS INCLUDING SCE-2787 publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: MIYAKE, A – start-page: 64 year: 1997 ident: WOS:000084428900013.2 publication-title: 17 S MED CHEM TSUK N contributor: fullname: KISHI K – volume: 46 start-page: 359 year: 1993 ident: WOS:A1993KN95800024 article-title: FK037, A NEW PARENTERAL CEPHALOSPORIN WITH A BROAD ANTIBACTERIAL SPECTRUM - SYNTHESIS AND ANTIBACTERIAL ACTIVITY publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: OHKI, H – volume: 5 start-page: 1685 year: 1997 ident: WOS:A1997XX51600019 article-title: Studies on 3'-quaternary ammonium cephalosporins .4. Synthesis and antibacterial activity of 3'-(2-alkyl-3-aminopyrazolium)cephalosporins related to FK037 publication-title: BIOORGANIC & MEDICINAL CHEMISTRY contributor: fullname: Ohki, H – volume: 37 start-page: 557 year: 1984 ident: WOS:A1984SS85500018 article-title: STUDIES OF 7BETA-[2-(AMINOARYL)ACETAMIDO]-CEPHALOSPORIN DERIVATIVES .3. SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS IN THE AMINOTHIADIAZOLE SERIES publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: GOTO, J – volume: 39 start-page: 1092 year: 1986 ident: WOS:A1986D698000010 article-title: SYNTHESIS AND STRUCTURE-ACTIVITY-RELATIONSHIPS OF A NEW SERIES OF CEPHALOSPORINS, BMY-28142 AND RELATED-COMPOUNDS publication-title: JOURNAL OF ANTIBIOTICS contributor: fullname: NAITO, T |
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| SubjectTerms | Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Biotechnology & Applied Microbiology cefoselis Cephalosporins - chemical synthesis Cephalosporins - pharmacology General pharmacology Immunology Life Sciences & Biomedicine Medical sciences Methicillin Resistance Microbiology Pharmacology & Pharmacy Pharmacology. Drug treatments Physicochemical properties. Structure-activity relationships Science & Technology Staphylococcus aureus Staphylococcus aureus - drug effects |
| Title | Synthesis and Biological Properties of a Novel Cephalosporin FR86521 Having Potent Activity Against Methicillin-resistant Staphylococcus aureus (MRSA) |
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