BIOMAT Database Logo BIOMAT Database Logo

Semisynthetic beta-lactam antibiotics. I. Synthesis and antibacterial activity of new ureidopenicillin derivatives having catechol moieties. 1986

N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga

The synthesis and antibacterial activity of new ureidopenicillin derivatives having catechol moieties in the 6-acyl side chain are described. These compounds showed remarkably strong activities against Pseudomonas aeruginosa. Especially, 6-[(R)-2-[3-(3,4-dihydroxybenzoyl)-3-methyl-1-ureido]-2- phenylacetamido]penicillanic acid (7a) had the most potent activity in vitro against Gram-negative bacteria, its activity being 30 approximately 60-fold greater than that of piperacillin against most strains of P. aeruginosa.

UI MeSH Term Description Entries
D008297 Male Males
D008815 Mice, Inbred Strains Genetically identical individuals developed from brother and sister matings which have been carried out for twenty or more generations, or by parent x offspring matings carried out with certain restrictions. All animals within an inbred strain trace back to a common ancestor in the twentieth generation. Inbred Mouse Strains,Inbred Strain of Mice,Inbred Strain of Mouse,Inbred Strains of Mice,Mouse, Inbred Strain,Inbred Mouse Strain,Mouse Inbred Strain,Mouse Inbred Strains,Mouse Strain, Inbred,Mouse Strains, Inbred,Strain, Inbred Mouse,Strains, Inbred Mouse
D010406 Penicillins A group of antibiotics that contain 6-aminopenicillanic acid with a side chain attached to the 6-amino group. The penicillin nucleus is the chief structural requirement for biological activity. The side-chain structure determines many of the antibacterial and pharmacological characteristics. (Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1065) Antibiotics, Penicillin,Penicillin,Penicillin Antibiotics
D011550 Pseudomonas aeruginosa A species of gram-negative, aerobic, rod-shaped bacteria commonly isolated from clinical specimens (wound, burn, and urinary tract infections). It is also found widely distributed in soil and water. P. aeruginosa is a major agent of nosocomial infection. Bacillus aeruginosus,Bacillus pyocyaneus,Bacterium aeruginosum,Bacterium pyocyaneum,Micrococcus pyocyaneus,Pseudomonas polycolor,Pseudomonas pyocyanea
D002396 Catechols A group of 1,2-benzenediols that contain the general formula R-C6H5O2. Pyrocatechols,o-Dihydroxybenzenes,ortho-Dihydroxybenzenes,o Dihydroxybenzenes,ortho Dihydroxybenzenes
D000818 Animals Unicellular or multicellular, heterotrophic organisms, that have sensation and the power of voluntary movement. Under the older five kingdom paradigm, Animalia was one of the kingdoms. Under the modern three domain model, Animalia represents one of the many groups in the domain EUKARYOTA. Animal,Metazoa,Animalia
D001424 Bacterial Infections Infections by bacteria, general or unspecified. Bacterial Disease,Bacterial Infection,Infection, Bacterial,Infections, Bacterial,Bacterial Diseases
D013329 Structure-Activity Relationship The relationship between the chemical structure of a compound and its biological or pharmacological activity. Compounds are often classed together because they have structural characteristics in common including shape, size, stereochemical arrangement, and distribution of functional groups. Relationship, Structure-Activity,Relationships, Structure-Activity,Structure Activity Relationship,Structure-Activity Relationships
D051379 Mice The common name for the genus Mus. Mice, House,Mus,Mus musculus,Mice, Laboratory,Mouse,Mouse, House,Mouse, Laboratory,Mouse, Swiss,Mus domesticus,Mus musculus domesticus,Swiss Mice,House Mice,House Mouse,Laboratory Mice,Laboratory Mouse,Mice, Swiss,Swiss Mouse,domesticus, Mus musculus

Related Publications

N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Synthesis and antibacterial activity of new ureido-beta-lactam derivatives having dialkyloxyphosphoryl-2-oxo-imidazolidinyl moieties.
March 1992, Die Pharmazie,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Semisynthetic beta-lactam antibiotics. I. Synthesis and antibacterial activity of 7 beta-[2-aryl-2-(aminoacetamido)acetamido]-cephalosporins.
September 1986, The Journal of antibiotics,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Semisynthetic beta-lactam antibiotics. VI. Synthesis and antimicrobial activity of alpha-hydrazonobenzylcephalosporins.
December 1985, Il Farmaco; edizione scientifica,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Semisynthetic beta-lactam antibiotics IX. Synthesis and antibacterial activity of 7-[2-(2-aminothiazol-4-yl)-2-sulfoacetamido]-cephalosporanic acid and its derivatives.
February 1983, Chemical & pharmaceutical bulletin,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Synthesis and antibacterial activity of novel aminothiazolyl beta-lactam derivatives.
March 1986, The Journal of antibiotics,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
[Reactions of derivatives of beta-lactam antibiotics with non-antibacterial biological activity].
January 2002, Acta pharmaceutica Hungarica,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Semisynthetic beta-lactam antibiotics. II. Synthesis and antibacterial activity of 7beta-[2-(acylamino)-2- (2-aminothiazol-4-yl)acetamido]cephalosporins.
September 1986, The Journal of antibiotics,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Semisynthetic beta-lactam antibiotics. III. Synthesis and antibacterial activity of 7 beta-[2-(2-aminothiazol-4-yl)-2-(substituted carbamoylmethoxyimino)acetamido]cephalosporins.
September 1986, The Journal of antibiotics,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Protection of hydroxyl in the synthesis of semisynthetic beta-lactam antibiotics.
September 1981, The Journal of antibiotics,
N Ohi, and B Aoki, and T Shinozaki, and K Moro, and T Noto, and T Nehashi, and H Okazaki, and I Matsunaga
Semisynthetic beta-lactam antibiotics. IV. Synthesis and antibacterial activity of 7 beta-[2-(hetero aromatic methoxyimino)-2-(2-aminothiazol-4-yl)acetamido]cephalosporins.
December 1988, The Journal of antibiotics,
Copied contents to your clipboard!