The Journal of Antibiotics
Online ISSN : 1881-1469
Print ISSN : 0021-8820
ISSN-L : 0021-8820
Volume 30, Issue 9
Displaying 1-19 of 19 articles from this issue
  • CEPHALOGLYCIN ANALOGS WITH SIX-MEMBERED HETEROCYCLES IN THE C-3 SIDE CHAIN
    TAKAYUKI NAITO, JUN OKUMURA, KEN-ICHI KASAI, KENJI MASUKO, HIDEAKI HOS ...
    1977 Volume 30 Issue 9 Pages 691-697
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    Cephaloglycin analogs with six-membered heterocycles in the C-3 side chain have been prepared by nucleophilic substitution of 7-aminocephalosporanic acid with appropriate azine thiols followed by 7-N-acylation with phenylglycine by the mixed anhydride method. Seventeen thiols of non-substituted or substituted pyridines, pyridazines, pyrimidines, pyrazines and triazines were used as the S-nucleophiles. In general, pyridazine thiols gave cephalosporins possessing good antimicrobial activity against both gram-positive and gram-negative bacteria. Among them 6-hydroxypyridazine-3-thiol gave the most active compound of this series, BB-S 118 (1f), which was significantly more active than cephalexin and cephaloglycin in vitro against gram-positive and gram-negative bacteria.
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  • 7-(O-AMINOMETHYLPHENYLACETAMIDO)CEPHALOSPORANIC ACIDS WITH SIX-MEMBERED HETEROCYCLES IN THE C-3 SIDE CHAIN
    TAKAYUKI NAITO, JUN OKUMURA, KEN-ICHI KASAI, KENJI MASUKO, HIDEAKI HOS ...
    1977 Volume 30 Issue 9 Pages 698-704
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    7-(o-Aminomethylphenylacetamido)cephalosporanic acids with six-membered heterocycles in the C-3 side chain were prepared by nucleophilic substitution of 7-ACA at the C-3 acetoxy group followed by N-acylation of the 7-amino group. The 7-side chain acid, o-aminomethylphenylacetic
    acid (5), was prepared by two new convenient routes, which involved SCHMIDT reaction of indanone (2) followed by cleavage of the lactam ring or reduction of o-cyanophenylacetic acid (10) starting from o-nitrotoluene. The antibacterial activity of the cephalosporins in this series depends on the heterocycle in the C-3 side chain. In general pyridazines gave cephalosporin derivatives possessing better activity than those with a pyridine or pyrimidine ring. The most active member of the new cephalosporins was 7-(o-aminomethylphenylacetamido)-
    3-(6-hydroxypyridazin-3-ylthiomethyl)-3-cephem-4-carboxylic acid (BB-S 150) (1g) which has in vitro antibacterial activity superior to cephalothin and cefazolin against both gram-negative and gram-positive organisms. The in ritro activity of BB-S 150 determined in mice was superior to cephalothin and comparable to cefazolin.
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  • 7-(O-AMINOMETHYLPHENYLACETAMIDO)CEPHALOSPORANIC ACIDS WITH BICYCLIC HETEROAROMATICS IN THE C-3 SIDE CHAIN
    TAKAYUKI NAITO, JUN OKUMURA, HAJIME KAMACHI, HIDEAKI HOSHI, HIROSHI KA ...
    1977 Volume 30 Issue 9 Pages 705-713
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    Bicyclic heteroaromatic thiols with a bridge-head nitrogen atom were used for nucleophilic substitution of 7-ACA at the C-3 acetoxy function followed by N-acylation of the 7-amino group with o-aminomethylphenylacetic acid to afford a series of new cephalosporins (24) with potent antibacterial activity against gram-positive and gram-negative organisms. The most active member of this series was 7-(o-aminomethylphenylacetamido)-3-(tetrazolo-[4, 5-b]pyridazin-6-ylthiomethyl)-3-cephem-4-carboxylic acid (BB-S 226) (24e) with antibacterial
    activity superior to cephalothin and cefazolin.
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  • HIKARU NAKAMURA, YOICHI IITAKA, TAKEJI KITAHARA, TAKAO OKAZAKI, YOSHIR ...
    1977 Volume 30 Issue 9 Pages 714-719
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    A new antibiotic, aplasmomycin, was isolated from a broth cultivated with a marine isolate of actinomycete, and inhibits Gram-positive bacteria in vitro and Plasmodium berghei in vivo. It is a natural ionophore and the structure of the Ag-salt was solved by an X-ray crystallographic analysis. It has a symmetric structure having boron in the centre of the molecule.
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  • H. BAUD, A. BETENCOURT, M. PEYRE, L. PENASSE
    1977 Volume 30 Issue 9 Pages 720-723
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    A mutant of a neomycin-producing Streptomyces fradiae was found which synthesizes ribostamycin instead of neomycin. After a reverse mutation new colonies were obtained producing neomycin again. Ribostamycin might thus be considered as an intermediate in the biosynthesis of neomycin.
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  • GERALD P. BODEY, SUSANNE WEAVER, THERESA PAN
    1977 Volume 30 Issue 9 Pages 724-729
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    The in vitroactivity of a new semi-synthetic penicillin, CP-35, 587, 3-(5-tetrazolyl) penam, was investigated against 496 clinical isolates of gram-negative bacilli and 113 clinical isolates of gram-positive cocci. All of the gram-positive cocci were sensitive to CP-35, 587 except penicillin G resistant isolates of Staphylococcus aureus. This antibiotic inhibited a majority of isolates of Escherichia coli, Klebsiellaspp. and Proteus mirabilisat a concentration of 6.25 μg/ml. Also, approximately half of the isolates of Serratia marcescensand Enterobacterspp. were inhibited at a concentration of 12.5μg/ml. CP-35, 587 was inactive when high concentrations of organisms were used as inocula. CP-35, 587 was more active than mezlocillin, azlocillin, amoxicillin, ticarcillin and carbenicillin against isolates of K. pneumoniae, but other
    penicillins were more active than CP-35, 587 against other species of gram-negative bacilli.
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  • PAUL ACTOR, JOSEPH R. GUARINI, JOSEPH URI, HENRY F. BARTUS, IHOR ZAJAC ...
    1977 Volume 30 Issue 9 Pages 730-735
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    Cefazaflur has a broad-spectrum of in vitro antibacterial activity equal to or greater than that of the commercially-available cephalosporins. In addition, cefazaflur has activity against isolates of Enterobacter, Citrobacter and indole-positive Proteus; however, this activity decreased markedly when the MIC determinations were carried out with a large inoculum size. A similar inoculum effect was observed with cefamandole, however, cefoxitin's activity was relatively unchanged at increased inoculum sizes. Human serum had a relatively small effect on the in vitro activity of cefazaflur.
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  • TOSHIHIDE NAKANISHI, FUSAO TOMITA, AKIRA FURUYA
    1977 Volume 30 Issue 9 Pages 736-742
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    The antibacterial activity of a new nucleoside antibiotic, 2'-amino-2'-deoxyguanosine (2AG), is reversed by guanosine and other purine nucleosides. 2AG is apparently taken up by E. coliby a mechanism different from that of guanosine; guanosine inhibits this uptake non-competitively. Insensitive E. colistrains and the resistant mutant obtained from the sensitive strain also took up 2AG.
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  • TOSHIHIDE NAKANISHI, FUSAO TOMITA, AKIRA FURUYA
    1977 Volume 30 Issue 9 Pages 743-748
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    The mechanism of inhibition of Escherichia coli by the new nucleoside antibiotic, 2'-amino-2'-deoxyguanosine (2AG), is described. Upon the addition of 2AG, the syntheses of macromolecules continued for 15 minutes. After this lag time, protein synthesis sharply decreased, RNA synthesis slightly decreased, but DNA synthesis was not affected. Tritiated 2AG was readily incorporated into the acid-soluble fraction of cells in the form of the mono-, di- and triphosphates. In the acid-soluble fraction, radioactivity was found only in the RNA fraction. The major part of the radioactivity was found to be guanylate; only 25% existed as the nucleotide of 2AG. In resistant strains of E. coli, there was a lower degree of phosphorylating activity
    and less incorporation of 2AG into RNA per unit of cell mass increase. These results suggest that 2AG inhibits growth by its incorporation into RNA and the subsequent disturbance of RNA function causing a block in protein synthesis.
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  • IBRAHIM R. SHIMI, SAFWAT SHOUKRY, ZEINAB ZAKI
    1977 Volume 30 Issue 9 Pages 749-752
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    The effects exerted by kuwaitimycin on synthesis of lipids as well as some metabolic activities of Bacillus subtilis were studied. The antibiotic not only arrested the incorporation of 14C-acetate into the microbial lipids but also altered the fatty acids pattern, contents of i-C 15, a-C 15, i-C 17 and a-C 17 were markedly reduced, concomitant with an increase in the contents of i-C 14 and n-C 14. Moreover, the rates of synthesis of phospholipids were decreased by the drug, especially that of phosphatidyl ethanolamine.
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  • RONALD N. JONES, E. HUGH GERLACH, PETER C. FUCHS
    1977 Volume 30 Issue 9 Pages 753-755
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
    Cefaclor [3-chloro-7-D-(2-phenylglycemamido)-3-cephem-4-carboxylic acid], has been reported by PRESTON and WICK as a new orally absorbed semi-synthetic cephalosporin (14th ICAAC Meeting, paper #426, 1974). This drug is structurally similar to the clinically available oral cephalosporins, cephradine and cephalexin.4) The significant structural difference is the substitution of a chloro group for the methyl group found in cephalexin and cephradine (Fig. 1). This study compares the in vitro antimicrobial activity of cefaclor with that of cephradine and cephalothin against seven commonly encountered bacterial species.
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  • JOSIP PLUSCEC, EMILY F. SABO, RICHARD O. NEUBECK, EUGENE R. WEAVER, HA ...
    1977 Volume 30 Issue 9 Pages 756-759
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
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  • C. G. FRIEDRICH, A. L. DEMAIN
    1977 Volume 30 Issue 9 Pages 760-761
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
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  • D. J. FLOURNOY
    1977 Volume 30 Issue 9 Pages 762-763
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
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  • SERGIO PENCO, FRANCESCO ANGELUCCI, ARISTIDE VIGEVANI, EMANUELE ARLANDI ...
    1977 Volume 30 Issue 9 Pages 764-766
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
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  • WILLIAM L. PARKER, MARLENE L. RATHNUM, LORETTA D. DEAN, MAXWELL W. NIM ...
    1977 Volume 30 Issue 9 Pages 767-769
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
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  • KENJI MAEDA, SAKIKO TAKAHASHI, MASAJI SEZAKI, KATSUHARU IINUMA, HIROSH ...
    1977 Volume 30 Issue 9 Pages 770-772
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
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  • SERGIO PENCO, GIANPIERO VICARIO, FRANCESCO ANGELUCCI, FEDERICO ARCAMON ...
    1977 Volume 30 Issue 9 Pages 773-774
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
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  • YUKIO FUJISAWA, MASAKAZU KIKUCHI, TOSHIHIKO KANZAKI
    1977 Volume 30 Issue 9 Pages 775-777
    Published: 1977
    Released on J-STAGE: April 12, 2006
    JOURNAL FREE ACCESS
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