Effect of antibiotic concentration on the killing of Staphylococcus aureus and Enterococcus faecalis: comparison of the novel penem, Men 10700, with other beta-lactam antibiotics

The key intermediate of monocyclic beta-lactams, N-benzyloxycarbonyl-3 S-amino-2-oxoazetidine(Ⅲ),was synthesized from L-( + )-2,3-diaminopropanoie acid(Ⅰ) by Ph_3P—(PyS)_2—CH_3CN system and N-benzyloxycarbonylation. Ⅰ was prepared from L(+)-aspartic acid by Schmidt rearrangement.Three derivatives(Ⅷa～c) of this monocyclic beta-lactam were prepared and their biological activities evaluated.

Lactam

Beta-lactam

Aspartic acid

BETA (programming language)

Source

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Citations (0)

Studies on Lactams IX. A Convenient Synthesis of Lactam Rings

Heterocycles (1981)

Haruo Ogura Kazuyoshi Takeda

The auto-cyclization reaction has been employed for the s y n t h e s ~s of lactam rings by means of reduction from w-carbo.benzoxyamino acid active esters in hlgh dilutlon method.

Lactam

Beta-lactam

10.3987/s-1981-01-0467

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Citations (7)

GT32-B New 20-Membered Macrocyclic Lactam Antibiotic.

The Journal of Antibiotics (1997)

ISAMI TAKAHASHI YASHUSHI ODA Y. NISHIIE Keiko Ochiai Tamio Mizukami

Lactam

Beta-lactam

10.7164/antibiotics.50.186

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Citations (26)

Enantiocontrolled Synthesis of the Antifungal .BETA.-Lactam(2R,5S)-2-(Hydroxymethyl)clavam.

Chemical and Pharmaceutical Bulletin (1991)

Toshiyuki Konosu S. OIDA

The antifungal β-lactam (2R, 5S)-2-(hydroxymethyl)clavam was synthesized in a convergent and stereocontrolled manner from methyl 6-phthalimidopenicillanate and 2, 3-O-isopropylidene-(R)-glyceraldehyde. Convenient methods of acetonide cleavage and phthalimide deblocking are also described.

Lactam

Hydroxymethyl

Acetonide

Convergent synthesis

Beta-lactam

10.1248/cpb.39.2212

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Citations (34)

Synthetic Studies on Carbapenem Antibiotics: A Carbon-introduced Reaction at the C-4 Position of a b-Lactam by Carbane Insertion Reaction

Heterocycles (1982)

Tetsuji Kametani Naoaki Kanaya Tomoko Mochizuki Toshio Honda

The reactlon of 4-thia-azetldlnones with dlazomalonates in the presence of a catalytic amount of rhodlum 111) acetate afforded the carbon-introduced products at the C -position of 4 O-lactams.Recently, much attention1-''

Lactam

Carbapenem

Beta-lactam

Insertion reaction

10.3987/r-1982-06-1023

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Citations (28)

Recent advances in the chemistry and biology of β-lactams and β-lactam antibiotics

Bioorganic & Medicinal Chemistry Letters (1993)

Gunda I. Georg

Lactam

Beta-lactam

10.1016/s0960-894x(01)80917-3

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Citations (18)

Nuclear analogs of β-lactam antibiotics. V. Synthesis of a benzo-fused carbocyclic β-lactam.

Tetrahedron Letters (1978)

Joseph A. Finkelstein Kenneth G. Holden Carl D. Perchonock

Lactam

Beta-lactam

Cephem

10.1016/s0040-4039(01)94624-6

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Citations (31)

Nocardicin A,a new monocyclic β-lactam antibiotic-3-In vitro evaluation

The Journal of Antibiotics (1977)

Minoru Nishida

Lactam

Beta-lactam

Source

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Citations (0)

beta-Lactams as Synthons. Synthesis of Heterocycles via beta-Lactam Cleavage

Heterocycles (1976)

Ajay K. Bose M. S. MANHAS S. G. AMIN

A beta-Lactams show high chemical reactivity and ease of molecular rearrangement and a r e therefore potential synthons of value.The present communication reviews the relevant literature and describes observation made in our laboratory and elsewhere.Suitably substituted beta-Lactams can lead to multiheteroatom cyclic compounds of various sizes including derivatives of carbostyril, coumarin, diazepin, oxazepin and thiazepin of potential interest to synthetic and medicinal chemists.

Synthon

Beta-lactam

Lactam

Cleavage (geology)

BETA (programming language)

10.3987/s-1976-01-0669

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Citations (37)

Synthesis of a cognition enhancing beta-lactam fused gamma-lactam

Tetrahedron Letters (1987)

James T. Drummond Graham Johnson

Lactam