1002965-95-8Relevant 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
, p. 2880 - 2894 (2011)
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.
Regioselective copper-catalyzed C-N and C-S bond formation using amines, thiols and halobenzoic acids
Liu, Shuanglong,Pestano, John Paul C.,Wolf, Christian
, p. 3519 - 3527 (2008/09/19)
A regioselective method for highly efficient C-N and C-S bond formation with 2-halobenzoic acids is described. The Cu/Cu2O-catalyzed reaction is carried out in 2-ethoxyethanol or ethylene glycol diethyl ether and does not require the use of strong base or other additives. This procedure eliminates the need for acid protection, tolerates a wide range of functional groups and provides aromatic and aliphatic amines and sulfides in 81-99% yield. Georg Thieme Verlag Stuttgart.
