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 inJournal of antibiotics Vol. 46; no. 5; pp. 833 - 839
Main Authors IIMURA, SEIJI, OKITA, TAKAAKI, KAMACHI, HAJIME, HASEGAWA, TOSHIFUMI, IMAE, KIYOTO, KAMEI, HIDEO, MASUYOSHI, SHINJI
Format Journal Article
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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.
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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Issue 5
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
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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
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– 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
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  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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ispartofPNX The Journal of Antibiotics, 1993/05/25, Vol.46(5), pp.833-839
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