New broad-spectrum cephalosporins with anti-pseudomonal activity. I. Synthesis and antibacterial activity of 7.BETA.-(D-2-((4-hydroxy-1,5-naphthyridine-3-carbonylamino)- and(4-hydroxypyridine-3-carbonylamino))-2-(4-hydoxyphenyl)acetamido)cephalosporins.

Abstract

The synthesis and the antibacterial activity of 7;2-[D-2-[(4-hydroxy-1,5-naphthyridine-3carbonylamino)-and (4-hydroxypyridine-3-carbonylamino)]-2-(4-hydroxyphenyl)acetamido]cephalosporins with various substituents at the 3-position in the cephem nucleus are described. These compounds exhibited strong antibacterial activities against a variety of Gram-positive and Gram-negative bacteria, including Pseudomonas aeruginosa and Enterobacter aerogenes, which are insensitive to cefazolin and cefmetazole. The compounds (3e, 4e) having a 1-methyl-I H-tetrazolylthiomethyl group at the 3-position appeared to show the best activity in each series. The 4-hydroxypyridine-3-carbonylamino derivative 4e gave higher peak serum concentrations and urinary recovery rates than those of the 4-hydroxy-1,5-naphthyridine derivative 3e when administered subcutaneously to mice and intramuscularly to rats.

The synthesis and absolute configuration of the novel ichthyotoxic diacyiglycerols, umbraculumin A and umbraculumin C

“…C13H20O2 requires C, 75.0; H, 9.7%); R, 0.35 (light petroleum+thyl acetate, 4: 1 + 1% MeOH); v,,,/cm-' 2950, 1685, 1635 and 963; 6, 1.23-1.37 (4 H, m), 1.37-1.45 (2 H, m), 1.61-1.62 (3 H, m), 1.95 (2 H, br s), 2.162. 21 (2 H, m), 5.37-5.40(2 H, m), 5.55 (1 H, d, J11.3), 6.10 (1 H, dt, J 15.0and 7.3), 6.63 (1 H, t, J 11.3), 7.31 (1 H, dd, J 11.3 and 15.0) and 10.0 (1 H, exch. ); 6, 17.9, 28.65, 28.7, 29.3, 32.4, 33.0, 114.7, 124.7, 127.0, 131.4, 147.1, 147.7 and 172.2; m/z 209 (M' + 1, 1.3%), 208 (M+, 24%), 97 (55), 81 (59), 55 (100) and 41 (56.5).…”