219739-90-9Relevant academic research and scientific papers
Syntheses of 5-amino-2-phenyl-4(3H)-pyrimidinone derivertives starting with glycine
Takahashi, Daisuke,Honda, Yutaka,Izawa, Kunisuke
scheme or table, p. 1089 - 1103 (2012/08/07)
N-Cbz derivative of 5-amino-2-phenyl-4(3H)-pyrimidinone was prepared from sodium salt of methyl hydroxymethylene glycinate and benzamidine hydrochloride in good yield. However, the reaction with N-substituted benzamidine did not proceed to give the desired pyrimidinone. In contrast, the reaction of 4-ethoxymethylene-2-phenyl-5(4H)-oxazolone readily prepared from hippuric acid and N-substituted benzamidine proceeded nicely to give 5-(benzoylamino)-6-oxo-2- phenyl-1(6H)-pyrimidineacetic acid in high yield.
Development of novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines
Burlison, Joseph A.,Avila, Christopher,Vielhauer, George,Lubbers, Donna J.,Holzbeierlein, Jeffrey,Blagg, Brian S. J.
, p. 2130 - 2137 (2008/09/19)
(Chemical Equation Presented) Recent studies have shown that the DNA gyrase inhibitor, novobiocin, binds to a previously unrecognized ATP-binding site located at the C-terminus of Hsp90 and induces degradation of Hsp90-dependent client proteins at ～700 μM. As a result of these studies, several analogues of the coumarin family of antibiotics have been reported and shown to exhibit increased Hsp90 inhibitory activity; however, the monomeric species lacked the ability to manifest anti-proliferative activity against cancer cell lines at concentrations tested. In an effort to develop more efficacious compounds that produce growth inhibitory activity against cancer cell lines, structure - activity relationships were investigated surrounding the prenylated benzamide side chain of the natural product. Results obtained from these studies have produced the first novobiocin analogues that manifest anti-proliferative activity against several cancer cell lines.
Synthesis and characterisation of some new N-glycosides containing substituted pyridopyrimidinone, pyrimidopyridazinone, thiazolopyrimidinone and quinolizin-4-one moiety
Simunek, Petr,Svete, Jurij,Stanovnik, Branko
experimental part, p. 2477 - 2491 (2011/04/17)
A series of new N-glycosides (D-glucosides, D-mannosides, L-and D-arabinosides, D-xylosides and one D-galactoside) containing heterocyclic moiety have been prepared by reaction of the corresponding heterocyclic amines with pyranoses in boiling methanol. The structures of the prepared compounds have been studied by means of proton and carbon NMR spectroscopy. In the most cases the products existed in DMSO solution as the single anomers. The Japan Institute of Heterocyclic Chemistry.
The synthesis of methyl 2-(benzyloxycarbonyl)amino-3- dimethylaminopropenoate. The synthesis of trisubstituted pyrroles, 3-amino- 2H-pyran-2-ones, fused 2H-pyran-2-ones and 4H-pyridin-4-ones
Toplak, Renata,Svete, Jurij,Stanovnik, Branko,Golic Grdadolnik, Simona
, p. 225 - 235 (2007/10/03)
Methyl 2-(benzyloxycarbonyl)amino-3-dimethylaminopropenoate (2) was prepared from methyl N-(benzyloxycarbonyl)glycinate (1) and t- butoxybis(dimethylamino)methane, and used as a reagent for preparation of substituted 3-(benzyloxycarbonyl)amino-4H-quinolizin-4-ones 5 and 6, -2H- pyran-2-ones 17-19, -2H-1-benzopyran-2-ones 28-31, and -naphthopyrans 32-35, -2H-pyrano[3,2-c]pyridine-2,5-dione 46, -pyrano[4,3-b]pyran-2,5-dione 47, - pyrano[3,2-c]benzopyran-2,5-dione 48, -pyrano[2,3-c]pyrazol-6-ones 49 and 50, -pyrano[2,3-d]pyrimidin-7-ones 51 and 52 derivatives. In the reaction of 2 with 1,3-diketones trisubstituted pyrroles 14-16 were formed. Selective removal of benzyloxycarbonyl group was achieved by catalytic transfer hydrogenation with Pd/C in the presence of cyclohexene to afford free 3- amino compounds 7, 8, 20, 36-38 and 53-57 in yields better than 80%.
