Synthesis of 3-(4-carbamoylpyridiniomethyl)-7B-(2-sulfophenyl-acetamido)-ceph-3-em-carboxylate monosodium salt labelled at [14C]carbamoyl and [1-14C]acetamido groups

✍ Scribed by Nobuyoshi Hayashi; Tadashi Toga; Norio Tada; Toshiyuki Azuma

• Publisher: John Wiley and Sons
• Year: 1978
• Tongue: French
• Weight: 218 KB
• Volume: 15
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580150155

✦ Synopsis

OC-Sulfobenzylpenicillin

as a new semi-synthetic penicillin having a broad antibiotic spectrum against Gram-positive and negative bacteria was first prepared in these laboratories and has already been supplied to clinical use. Moreover, many semisynthetic penicillins and cephalosporins have been synthesized in order to seek for high effective antipseudomonal medicament without toxicity. Among these synthetic and biological studies, 3-(4-carbamoylpyridiniomethyl)-78-(D-2-sulfophenylacet~ido)-ceph-3-em-4-carboxylate monosodium salt (SCE-129) appeared to be one of the most potent antipseudomonal compounds ever known in the)-lactam antibiotics. (2) [ C]carbamoylpyridiniomethyl)-7~-(D-2-sulfophenylacet~ido)-ceph-3-em-4-carboxylate monosodium salt (VI) and 3-(4-carbamoylpyridiniomethyl) -7b-(DL-2-sulfophenyl-[ 1-14C] acetamido) -ceph-3-em-4-carboxylate monosodium salt (XII). By the well known procedure, [~arboxyl-~~C] isonicotinic acid (111) was obtained from the reaction of 14C02 with 4-pyridyl lithium which was prepared from 4-bromopyridine, and treated with S0Cl2, followed by ammonia to give [~arbonyl-~'C] isonicotinamide (V) . This paper deals with the syntheses of 3-(4-14 (3) Condensation of V with 7)-(D-2-0 362-48O3/70lQO l5-0489 $0 1.00 019713 by John Wiley & Sons Ltd.