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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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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
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C. G. FRIEDRICH, A. L. DEMAIN
1977 Volume 30 Issue 9 Pages
760-761
Published: 1977
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D. J. FLOURNOY
1977 Volume 30 Issue 9 Pages
762-763
Published: 1977
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SERGIO PENCO, FRANCESCO ANGELUCCI, ARISTIDE VIGEVANI, EMANUELE ARLANDI ...
1977 Volume 30 Issue 9 Pages
764-766
Published: 1977
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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
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KENJI MAEDA, SAKIKO TAKAHASHI, MASAJI SEZAKI, KATSUHARU IINUMA, HIROSH ...
1977 Volume 30 Issue 9 Pages
770-772
Published: 1977
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SERGIO PENCO, GIANPIERO VICARIO, FRANCESCO ANGELUCCI, FEDERICO ARCAMON ...
1977 Volume 30 Issue 9 Pages
773-774
Published: 1977
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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
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