Results 71 to 80 of about 697 (107)

Formal synthesis of Thienamycin

The Journal of Antibiotics, 2017
A formal synthesis of Thienamycin from ethyl (E)-crotonate and a cyclic five-membered nitrone derived from 2-deoxy-d-ribose is described. The synthesis involves 1,3-dipolar cycloaddition, cleavage of the N-O bond in the adduct, and intramolecular N-acylation to afford a bicyclic carbapenam skeleton.
Michał, Pieczykolan, Bartłomiej, Furman, Marek, Chmielewski   +2 more
openaire   +2 more sources

Thienamycin: development of imipenem-cilastatin

Journal of Antimicrobial Chemotherapy, 1983
Thienamycin, a natural product produced by Streptomyces cattleya is the first representative of a unique class of beta-lactam antibiotics, the carbapenems. Despite its outstanding potency and antibacterial spectrum, thienamycin was itself unsuited for further development because of its chemical instability in concentrated solution and in the solid ...
F M, Kahan, H, Kropp, J G, Sundelof, J, Birnbaum   +3 more
openaire   +2 more sources

ChemInform Abstract: THIENAMYCIN TOTAL SYNTHESIS. 3. TOTAL SYNTHESIS OF (.+‐.)‐THIENAMYCIN AND (.+‐.)‐8‐EPITHIENAMYCIN

Chemischer Informationsdienst, 1980
AbstractAus dem früher aufgeführten sterisch definierten Azetidinon‐carbinol (I) entsteht der Aldehyd (II), der in das Dithioacetal (III) übergeführt wird und zu (IVa) eliminiert.
S. M. SCHMITT, D. B. R. JOHNSTON, B. G. CHRISTENSEN   +2 more
openaire   +1 more source

Thienamycin-imipenem

2000
Abstract Despite the outstanding antibacterial profile of thienamycin 1, this compound was not considered attractive for clinical use because of its high chemical instability, found to be both pH- and concentration-dependent.4.
Walter Cabri, Romano Di Fabio
openaire   +1 more source

A practical synthesis of (±)-thienamycin

Tetrahedron Letters, 1980
Abstract An efficient and operationally simple synthesis of (±)-thienamycin is described.
D.G. Melillo, I. Shinkai, T. Liu, K. Ryan, M. Sletzinger   +4 more
openaire   +1 more source

A formal synthesis of (±)-thienamycin

J. Chem. Soc., Chem. Commun., 1986
An α-silylethylidene-β-lactam is generated via chlorosulphonyl isocyanate (CSI) addition to a silylated allenyl sulphide and converted into a key intermediate for the synthesis of thienamycin.
John D. Buynak, Jacob Mathew, M. Narayana Rao   +2 more
openaire   +1 more source

Total synthesis of thienamycin analogs. 1. Synthesis of the thienamycin nucleus and dl-decysteaminylthienamycin

Journal of the American Chemical Society, 1978
Ausgehend von dem Azetidinon (I) bzw. dem Oxaazabicyclooctanon (Va) wird das Carbapenem-carboxylat (IVb) bzw. das dl-Descysteaminylthienamycinsalz dl-(VIIIb) synthetisiert.
L. D. Cama, B. G. Christensen
openaire   +1 more source

A comparative in vitro study of thienamycin

Infection, 1982
The in vitro activity of thienamycin was compared to that of other antibiotics against a large panel of bacteria obtained in blood cultures from cancer patients. This compound was the most active against gram-positive cocci and also proved to be extremely active against the gram-negative bacteria.
V, Fainstein, B, LeBlanc, S, Weaver, G P, Bodey   +3 more
openaire   +2 more sources

Total synthesis of thienamycin analogs. II Synthesis of 2-alkyl and 2-aryl thienamycin nuclei

Tetrahedron Letters, 1980
Abstract A new general synthesis leading to 2-alkyl and 2-aryl-1-carba-2-penem-3-carboxylic acids involves the preparation of a key thiolester intermediate 3. This is reacted with Me2CuLi or (C6H5)2MgCuX to give the corresponding methyl or phenyl ketone which undergoes a Wittig reaction to give the desired penems, which can be deblocked ...
L. Cama, B.G. Christensen
openaire   +1 more source

Preparation and antibacterial activity of .DELTA.1-thienamycin

Journal of Medicinal Chemistry, 1981
delta 1-Thienamycin (2), a double-bond isomer of thienamycin, was prepared by isomerizing N-[[(p-nitrobenzyl)oxy]-carbonyl]thienamycin p-nitrobenzyl ester (5b) with DBU in Me2SO followed by hydrogenolysis of the protecting groups. When evaluated in a disc-diffusion antibacterial assay, delta 1-thienamycin was found to be essentially devoid of activity.
D H, Shih, R W, Ratcliffe
openaire   +2 more sources