99397-29-2Relevant academic research and scientific papers
MONOBACTAM ORGANIC COMPOUNDS FOR THE TREATMENT OF BACTERIAL INFECTIONS
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Paragraph 0412; 0413, (2015/11/10)
This invention pertains generally to antibacterial compounds of Formula I, as further described herein, and pharmaceutically acceptable salts and formulations thereof. In certain aspects, the invention pertains to methods of using such compounds to treat infections such as those caused by Gram-negative bacteria.
SAR and structural analysis of siderophore-conjugated monocarbam inhibitors of pseudomonas aeruginosa PBP3
Murphy-Benenato, Kerry E.,Dangel, Brian,Davis, Hajnalka E.,Durand-Réville, Thomas F.,Ferguson, Andrew D.,Gao, Ning,Jahi?, Haris,Mueller, John P.,Manyak, Erika L.,Quiroga, Olga,Rooney, Michael,Sha, Li,Sylvester, Mark,Wu, Frank,Zambrowski, Mark,Zhao, Shannon X.
supporting information, p. 537 - 542 (2015/05/27)
A main challenge in the development of new agents for the treatment of Pseudomonas aeruginosa infections is the identification of chemotypes that efficiently penetrate the cell envelope and are not susceptible to established resistance mechanisms. Siderophore-conjugated monocarbams are attractive because of their ability to hijack the bacteria's iron uptake machinery for transport into the periplasm and their inherent stability to metallo-β-lactamases. Through development of the SAR we identified a number of modifications to the scaffold that afforded active anti-P. aeruginosa agents with good physicochemical properties. Through crystallographic efforts we gained a better understanding into how these compounds bind to the target penicillin binding protein PBP3 and factors to consider for future design.
MONOBACTAMS
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, (2012/06/16)
The present invention is directed to a new class of monobactam derivatives and their use for treating bacterial infections.
Microbiological enantioselective synthesis of (S) and (R) 4-(p-anisyloxy)-3-hydroxybutyrates as new chiral building blocks for the synthesis of β-lactam antibiotics
Banfi, Luca,Cascio, Giuseppe,Ghiron, Chiara,Guanti, Giuseppe,Manghisi, Elso,Narisano, Enrica,Riva, Renata
, p. 11983 - 11994 (2007/10/02)
Both enantiomers of 4-p-anisyloxy-3-hydroxybutanoates 4 have been prepared in high e.e. by reduction of the corresponding β-ketoesters or β-ketocarboxylates with immobilized fermenting baker's yeast. The utility of these new chiral building blocks in the
Enantiospecific and Diastereoselective Synthesis of cis Monobactams through Electrophilic Amination of Chiral 3-Hydroxyesters
Banfi, Luca,Cascio, Giuseppe,Guanti, Giuseppe,Manghisi, Elso,Narisano, Enrica,Riva, Renata
, p. 11967 - 11982 (2007/10/02)
A new efficient entry into cis monobactams starting from β-hydroxyesters is reported.This preparation is based on the stereoselective "electrophilic amination" of β-hydroxyester dianions and on Miller's biomimetic synthesis of the β-lactam nucleus.By this route, key intermediates for the preparation of pharmacologically important cis aztreonam 2 and carumonam 3 were prepared.
Stereoselective Synthesis of β-Lactams by Oxidative Coupling of Dianions of Acyclic Tertiary Amides
Kawabata, Takeo,Minami, Tatsuya,Hiyama, Tamejiro
, p. 1864 - 1873 (2007/10/02)
Tertiary amides RCH2CON(R')CH2Z, where Z is an electron-withdrawing group, were converted into dianions by treatment with 2 equiv of n-butyllithium or tert-butyllithium, and the dianions were oxidized with N-iodoosuccinimide (NIS) or a Cu(II) carboxylate to form β-lactams stereoselectively.The stereochemistry of β-lactam formation depends on the oxidant; NIS is cis-selective, whereas Cu(II) is nonselective or slightly trans-selective.A high degree of asymmetric induction in the formation of β-lactams was achieved by using (R)-1-phenylethylamines a chiral auxiliary.This asymmetric ring closure was applied to the preparation of cis-β-lactam 31, an intermediate for the synthesis of the monobactam antibiotic carumonam.
Optically active β-lactams and method of their production
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, (2008/06/13)
Optically active β-lactams of the general formula STR1 wherein R1 is an amino or protected amino group, R2 is an organic residue bonding through a carbon atom thereof and R3 is the residue remaining after removal of the α-
An Examination of O-2-Isocephems as Orally Absorbable Antibiotics
Mastalerz, Harold,Menard, Marcel,Vinet, Vivianne,Desiderio, James,Fung-Tomc, Joan,et al.
, p. 1190 - 1196 (2007/10/02)
The synthesis and structure-activity relationships of a series of orally absorbed O-2-isocephems are described.These compounds possessed a D-amino substituent at the 7-position while the substituent at the 3-position was varied.Relative to the analogous cephems, the O-2-isocephems exhibited comparable to better activity against Gram-positive organisms.Against Gram-negative organisms, their activity was variable but did indicate a lower β-lactamase stability.Following oral administration, the O-2-isocephems generally exhibited longer half-lives but lower Cmax's and urinary recoveries.
