SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF CEPHALOSPORINS HAVING A CATECHOL IN THE C3 SIDE CHAIN
Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4-ylcarbonyloxy)methylcephalosporin (14) and 3-[(E)-3-(catechol-4-ylcarbonyloxy)-l-propen-l-yl]cephalosporin (10) showed excellent activity against G...
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Published in | Journal of antibiotics Vol. 46; no. 5; pp. 833 - 839 |
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Main Authors | , , , , , , |
Format | Journal Article |
Language | English |
Published |
TOKYO
JAPAN ANTIBIOTICS RESEARCH ASSOCIATION
1993
JAPAN ANTIBIOT RES ASSN Japan Antibiotics Research Association |
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Abstract | Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4-ylcarbonyloxy)methylcephalosporin (14) and 3-[(E)-3-(catechol-4-ylcarbonyloxy)-l-propen-l-yl]cephalosporin (10) showed excellent activity against Gram-negative activity including ceftazidime-resistant Escherichia coli, Pseudomonas aeruginosa, Xanthomonas maltophilia and Pseudomonas cepacia. |
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AbstractList | Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4- ylcarbonyloxy)methylcephalosporin (14) and 3-[(E)-3-(catechol-4-ylcarbonyloxy)-1-propen-1-yl]cephalospo rin (10) showed excellent activity against Gram-negative activity including ceftazidime-resistant Escherichia coli, Pseudomonas aeruginosa, Xanthomonas maltophilia and Pseudomonas cepacia. Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4- ylcarbonyloxy)methylcephalosporin (14) and 3-[(E)-3-(catechol-4-ylcarbonyloxy)-1-propen-1-yl]cephalospo rin (10) showed excellent activity against Gram-negative activity including ceftazidime-resistant Escherichia coli, Pseudomonas aeruginosa, Xanthomonas maltophilia and Pseudomonas cepacia.Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4- ylcarbonyloxy)methylcephalosporin (14) and 3-[(E)-3-(catechol-4-ylcarbonyloxy)-1-propen-1-yl]cephalospo rin (10) showed excellent activity against Gram-negative activity including ceftazidime-resistant Escherichia coli, Pseudomonas aeruginosa, Xanthomonas maltophilia and Pseudomonas cepacia. CePhalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4-ylcarbonyloxy)methylcephalosporin (14) and 3-[(E)-3-(catechol-4-ylcarbonyloxy)-1-propen-1-yl]cephalosporin (10) showed excellent activity against Gram-negative activity including ceftazidime-resistant Escherichia coli, Pseudomonas aeruginosa, Xanthomonas maltophilia and Pseudomonas cepacia. Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4-ylcarbonyloxy)methylcephalosporin (14) and 3-[(E)-3-(catechol-4-ylcarbonyloxy)-l-propen-l-yl]cephalosporin (10) showed excellent activity against Gram-negative activity including ceftazidime-resistant Escherichia coli, Pseudomonas aeruginosa, Xanthomonas maltophilia and Pseudomonas cepacia. |
Author | IIMURA, SEIJI OKITA, TAKAAKI IMAE, KIYOTO MASUYOSHI, SHINJI HASEGAWA, TOSHIFUMI KAMACHI, HAJIME KAMEI, HIDEO |
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Keywords | M14659 INVITRO ANTIPSEUDOMONAL CEPHALOSPORIN E-0702 Antibiotic Cephalosporin derivatives Microorganism growth Sensitivity resistance Synthesis Structure activity relation Molecular structure Minimum inhibitory concentration Microorganism culture Bacteria Antibacterial agent In vitro |
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References | 1) KATSU, K.; K. KITOH, M. INOUE & S. MITSUHASHI: In vitro antibacterial activity of E-0702, a new semisynthetic cephalosporin. Antimicrob. Agents Chemother. 22: 181-185, 1982 4) NAKAGAWA, S.; M. SANADA, K. MATSUDA, T. HASHIZUME, Y. ASAHI, R. USHIJIMA, N. OHTAKE & N. TANAKA: In vitro and in vivo antibacterial activities of BO-1341, a new antipseudomonal cephalosporin. Antimicrob. Agents Chemother. 33: 1423-1427, 1989 6) SANADA, M.; T. HASHIZUME, K. MATSUDA, S. NAKAGAWA & N. TANAKA: Mode of action of BO-1341: transport pathway through the outer membrane of Escherichia coli. Drugs Exptl. Clin. Res. 14: 397 - 402, 1988 7) MOCHIZUKI, H.; H. YAMADA, Y. OIKAWA, K. MURAKAMI, J. ISHIGURO, H. KOSUZUME, N. AIZAWA & E. MOCHIDA: Bactericidal activity of M14659 enhanced in low-iron environments. Antimicrob. Agents Chemother. 32: 1648-1654,1988 9) KAMACHI, H.; T. OKITA, H. HOSHI, S. OKUYAMA & T. NAITO: Synthesis of geometrical isomers of 3-(3-acetoxy and 3-carbamoyloxy-l-propenyl)cephalosporins and their structure-activity relationships. J. Antibiotics 45: 998-1001,1992 10) WEI, C. C; D. BARTKOVITZ & K. F. WEST: A facile and general synthesis of 3-(acyloxy)cephalosporins. J. Org. Chem. 57: 4027-4030, 1992 11) CORBETT, D. F.; C. H. FRIEDRICH & R. SOUTHGATE (Beecham): New aryloxymethyl-7-acylamino-3-cephem derivatives and analogues useful as broad spectrum antibacterials. Jpn. Kokai 152389 ('88), June 24, 1988 5) WATANABE, N.; T. NAGASU, K. KATSU & K. KITOH: E-0702, a new cephalosporin, is incorporated into Escherichia coli cells via the to".#-dependent iron transport system. Antimicrob. Agents Chemother. 31: 497 - 504, 1987 8) KAMACHI, H.; M. OKA, Y. NARITA, S. IIMURA, S. ABURAKI, H. YAMASHITA, K. TOMATSU, J. OKUMURA & T. NAITO: Synthesis of a new series of cephalosporins having 3-substituted-ammonio-l-propenyl group as the C-3 side chain.? J. Antibiotics 43: 533-543, 1990 2) NAKAGAWA, S.; M. SANADA, K. MATSUDA, N. HAZUMI & N. TANAKA: Biological activity of BO-1236, a new antipseudomonal cephalosporin. Antimicrob. Agents Chemother. 31: 1100 - 1105, 1987 3) MOCHIZUKI, H.; Y. OIKAWA, H. YAMADA, S. KUSAKABE, T. SHIIHARA, K. MURAKAMI, K. KATO, J. ISHIGURO & H. KOSUZUME: Antibacterial and pharmacokinetic properties of Ml4659, a new injectable semisynthetic cephalosporin. J. Antibiotics 41: 377-391, 1988 WATANABE, NA (WOS:A1987G764500003) 1987; 31 KAMACHI, H (WOS:A1990DK69300011) 1990; 43 MOCHIZUKI, H (WOS:A1988Q805400011) 1988; 32 MOCHIZUKI, H (WOS:A1988M634900014) 1988; 41 SANADA, M (WOS:A1988Q737000005) 1988; 14 (WOS:A1993LD99900017.1) 1988 KATSU, K (WOS:A1982PA37700001) 1982; 22 KAMACHI, H (WOS:A1992JB05600025) 1992; 45 NAKAGAWA, S (WOS:A1987J082500025) 1987; 31 NAKAGAWA, S (WOS:A1989AP32900003) 1989; 33 WEI, CC (WOS:A1992JC51100057) 1992; 57 |
References_xml | – reference: 5) WATANABE, N.; T. NAGASU, K. KATSU & K. KITOH: E-0702, a new cephalosporin, is incorporated into Escherichia coli cells via the to".#-dependent iron transport system. Antimicrob. Agents Chemother. 31: 497 - 504, 1987 – reference: 9) KAMACHI, H.; T. OKITA, H. HOSHI, S. OKUYAMA & T. NAITO: Synthesis of geometrical isomers of 3-(3-acetoxy and 3-carbamoyloxy-l-propenyl)cephalosporins and their structure-activity relationships. J. Antibiotics 45: 998-1001,1992 – reference: 7) MOCHIZUKI, H.; H. YAMADA, Y. OIKAWA, K. MURAKAMI, J. ISHIGURO, H. KOSUZUME, N. AIZAWA & E. MOCHIDA: Bactericidal activity of M14659 enhanced in low-iron environments. Antimicrob. Agents Chemother. 32: 1648-1654,1988 – reference: 3) MOCHIZUKI, H.; Y. OIKAWA, H. YAMADA, S. KUSAKABE, T. SHIIHARA, K. MURAKAMI, K. KATO, J. ISHIGURO & H. KOSUZUME: Antibacterial and pharmacokinetic properties of Ml4659, a new injectable semisynthetic cephalosporin. J. Antibiotics 41: 377-391, 1988 – reference: 8) KAMACHI, H.; M. OKA, Y. NARITA, S. IIMURA, S. ABURAKI, H. YAMASHITA, K. TOMATSU, J. OKUMURA & T. NAITO: Synthesis of a new series of cephalosporins having 3-substituted-ammonio-l-propenyl group as the C-3 side chain.? J. Antibiotics 43: 533-543, 1990 – reference: 2) NAKAGAWA, S.; M. SANADA, K. MATSUDA, N. HAZUMI & N. TANAKA: Biological activity of BO-1236, a new antipseudomonal cephalosporin. Antimicrob. Agents Chemother. 31: 1100 - 1105, 1987 – reference: 4) NAKAGAWA, S.; M. SANADA, K. MATSUDA, T. HASHIZUME, Y. ASAHI, R. USHIJIMA, N. OHTAKE & N. TANAKA: In vitro and in vivo antibacterial activities of BO-1341, a new antipseudomonal cephalosporin. Antimicrob. Agents Chemother. 33: 1423-1427, 1989 – reference: 11) CORBETT, D. F.; C. H. FRIEDRICH & R. SOUTHGATE (Beecham): New aryloxymethyl-7-acylamino-3-cephem derivatives and analogues useful as broad spectrum antibacterials. Jpn. Kokai 152389 ('88), June 24, 1988 – reference: 6) SANADA, M.; T. HASHIZUME, K. MATSUDA, S. NAKAGAWA & N. TANAKA: Mode of action of BO-1341: transport pathway through the outer membrane of Escherichia coli. Drugs Exptl. Clin. Res. 14: 397 - 402, 1988 – reference: 1) KATSU, K.; K. KITOH, M. INOUE & S. MITSUHASHI: In vitro antibacterial activity of E-0702, a new semisynthetic cephalosporin. Antimicrob. Agents Chemother. 22: 181-185, 1982 – reference: 10) WEI, C. C; D. BARTKOVITZ & K. F. WEST: A facile and general synthesis of 3-(acyloxy)cephalosporins. J. Org. Chem. 57: 4027-4030, 1992 – volume: 31 start-page: 1100 year: 1987 ident: WOS:A1987J082500025 article-title: BIOLOGICAL-ACTIVITY OF BO-1236, A NEW ANTIPSEUDOMONAL CEPHALOSPORIN publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY – volume: 32 start-page: 1648 year: 1988 ident: WOS:A1988Q805400011 article-title: BACTERICIDAL ACTIVITY OF M14659 ENHANCED IN LOW-IRON ENVIRONMENTS publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY – volume: 45 start-page: 998 year: 1992 ident: WOS:A1992JB05600025 article-title: SYNTHESIS OF GEOMETRICAL-ISOMERS OF 3-(3-ACETOXY-1-PROPENYL)CEPHALOSPORIN AND 3-(3-CARBAMOYLOXY-1-PROPENYL)CEPHALOSPORIN AND THEIR STRUCTURE-ACTIVITY-RELATIONSHIPS publication-title: JOURNAL OF ANTIBIOTICS – volume: 14 start-page: 397 year: 1988 ident: WOS:A1988Q737000005 article-title: MODE OF ACTION OF BO-1341 - TRANSPORT PATHWAY THROUGH THE OUTER-MEMBRANE OF ESCHERICHIA-COLI publication-title: DRUGS UNDER EXPERIMENTAL AND CLINICAL RESEARCH – volume: 22 start-page: 181 year: 1982 ident: WOS:A1982PA37700001 article-title: INVITRO ANTIBACTERIAL ACTIVITY OF E-0702, A NEW SEMI-SYNTHETIC CEPHALOSPORIN publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY – year: 1988 ident: WOS:A1993LD99900017.1 – volume: 33 start-page: 1423 year: 1989 ident: WOS:A1989AP32900003 article-title: INVITRO AND INVIVO ANTIBACTERIAL ACTIVITIES OF BO-1341, A NEW ANTIPSEUDOMONAL CEPHALOSPORIN publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY – volume: 31 start-page: 497 year: 1987 ident: WOS:A1987G764500003 article-title: E-0702, A NEW CEPHALOSPORIN, IS INCORPORATED INTO ESCHERICHIA-COLI-CELLS VIA THE TONB-DEPENDENT IRON TRANSPORT-SYSTEM publication-title: ANTIMICROBIAL AGENTS AND CHEMOTHERAPY – volume: 57 start-page: 4027 year: 1992 ident: WOS:A1992JC51100057 article-title: A FACILE AND GENERAL-SYNTHESIS OF 3-(ACYLOXY)CEPHALOSPORINS publication-title: JOURNAL OF ORGANIC CHEMISTRY – volume: 41 start-page: 377 year: 1988 ident: WOS:A1988M634900014 article-title: ANTIBACTERIAL AND PHARMACOKINETIC PROPERTIES OF M14659, A NEW INJECTABLE SEMISYNTHETIC CEPHALOSPORIN publication-title: JOURNAL OF ANTIBIOTICS – volume: 43 start-page: 533 year: 1990 ident: WOS:A1990DK69300011 article-title: SYNTHESIS OF A NEW SERIES OF CEPHALOSPORINS HAVING 3-SUBSTITUTED-AMMONIO-1-PROPENYL GROUP AS THE C-3 SIDE-CHAIN publication-title: JOURNAL OF ANTIBIOTICS |
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Snippet | Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them,... CePhalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them,... Cephalosporins having a catechol through a variety of linkages to the C3 position and a different C7 side chain were prepared. Among them, 3-(catechol-4-... |
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SubjectTerms | Antibacterial agents Antibiotics. Antiinfectious agents. Antiparasitic agents Biological and medical sciences Biotechnology & Applied Microbiology Cephalosporins - chemical synthesis Cephalosporins - pharmacology Immunology Life Sciences & Biomedicine Medical sciences Microbial Sensitivity Tests Microbiology Pharmacology & Pharmacy Pharmacology. Drug treatments Science & Technology Structure-Activity Relationship |
Title | SYNTHESIS AND ANTIBACTERIAL ACTIVITY OF CEPHALOSPORINS HAVING A CATECHOL IN THE C3 SIDE CHAIN |
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