58660-59-6Relevant academic research and scientific papers
Second-generation sulfonamide inhibitors of d-glutamic acid-adding enzyme: Activity optimisation with conformationally rigid analogues of d-glutamic acid
Sosi?, Izidor,Barreteau, Hélne,Sim?i?, Mihael,?ink, Roman,Cesar, Jo?ko,Zega, Anamarija,Grdadolnik, Simona Goli?,Contreras-Martel, Carlos,Dessen, Andréa,Amoroso, Ana,Joris, Bernard,Blanot, Didier,Gobec, Stanislav
experimental part, p. 2880 - 2894 (2011/07/08)
d-Glutamic acid-adding enzyme (MurD) catalyses the essential addition of d-glutamic acid to the cytoplasmic peptidoglycan precursor UDP-N-acetylmuramoyl- l-alanine, and as such it represents an important antibacterial drug-discovery target enzyme. Based on a series of naphthalene-N-sulfonyl-d-Glu derivatives synthesised recently, we synthesised two series of new, optimised sulfonamide inhibitors of MurD that incorporate rigidified mimetics of d-Glu. The compounds that contained either constrained d-Glu or related rigid d-Glu mimetics showed significantly better inhibitory activities than the parent compounds, thereby confirming the advantage of molecular rigidisation in the design of MurD inhibitors. The binding modes of the best inhibitors were examined with high-resolution NMR spectroscopy and X-ray crystallography. We have solved a new crystal structure of the complex of MurD with an inhibitor bearing a 4-aminocyclohexane-1,3-dicarboxyl moiety. These data provide an additional step towards the development of sulfonamide inhibitors with potential antibacterial activities.
Interrupted Polymerization of Acrylates: Sequential Michael-Michael-Dieckmann Cyclizations for Easy, One-Pot, 2 + 2 + 2 Construction of Polyfunctionalized Cyclohexanones
Posner, Gary H.,Shulman-Roskes, Ellen M.
, p. 3514 - 3515 (2007/10/02)
In THF at -78 deg C, lithio enolates of several different acyclic and cyclic carboxylate esters react cleanly with 2 equiv of an acrylate ester via a Michael-Michael-Dieckmann cyclization sequence to form polyfunctionalized cyclohexanones in 45-72percent overall yields; this process represents useful, controlled interruptions of polymerization reactions.
Synthetic Studies in Carbocyclic Systems : Part I - A new Synthesis of Nopinone
Murthi, G. S. S.,Mazumder, Alok
, p. 339 - 340 (2007/10/02)
Base-induced intramolecular nucleophilic displacement of the tosyloxy group of 4-isopropyl-7-tosyloxycyclohexanone affords nopinone , identical with an authentic specimen.
