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Diethyl N (diethyl + n)
Selected AbstractsOxidation of diethyl N -sulfinylphos-phoramidatesHETEROATOM CHEMISTRY, Issue 5 2008yna Mielniczak It is reported that the diethyl N -sulfinylphosphoramidate (1a) is oxidized with iodoso- and/or iodoxybenzene as well as with organic peroxides, to give diethyl N -sulfonylphosphoramidate (7a). The latter was generated in situ at low temperature and trapped with dialkyl phosphoramidates, affording the N,N, bis(dialkyl phosphor)sulfamides 3a,c. The oxidation of 1a with cumene peroxide in the presence of 2,2-dimethyl-propan-1-ol (9) produced the diethylphosphor- N -[2,2-dimethylpropyl]sulfamate (10a). © 2008 Wiley Periodicals, Inc. Heteroatom Chem 19:530,536, 2008; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20474 [source] Synthesis and biological evaluation of 9-thia-5,10-dideazafolic acidJOURNAL OF HETEROCYCLIC CHEMISTRY, Issue 5 2002Mark Wall The folate analogue, 9-thia-5,10-dideazafolic acid (3b), was obtained in an efficient two-step procedure in an overall yield of 60%. The previously unknown intermediate dimethyl-thiocarbamic acid S-(2-amino-3,4-dihydo-4-oxo-pyrido[2,3- d]pyrimidin-6-yl) ester (5) was prepared via the condensation of 2,6-diamino-3H -pyrimidin-4-one and S-(2-malonaldehyde)-1,1,3,3-tetramethylthiouronium bromide (4). Compound 5, in a one pot procedure, was deprotected using sodium hydroxide and then coupled to diethyl N -[(4-chloromethyl)benzoyl]-L-glutamate, followed by saponification of the ethyl esters to give the 9-thia-5,10-dideazafolic acid (3b). Compound 3b was a potent inhibitor of human 5-aminoimidazole-4-carboxamide ribonucleotide transformylase (Ki of 8 ± 5 ,M) and showed no inhibition of human glycinamide ribonu-cleotide transformylase at concentrations as high as 50 ,M. Compound 3b was screened by the National Cancer Institute Developmental Therapeutics Program against 60 human tumors and was found to be active against a leukemia RPMI-8226 cell line where the LC50 was 1 ,M. [source] Hydrogen-bonding patterns in two aroylthiocarbamates and two aroylimidothiocarbonatesACTA CRYSTALLOGRAPHICA SECTION C, Issue 3 2010Henry Insuasty In O -ethyl N -benzoylthiocarbamate, C10H11NO2S, the molecules are linked into sheets by a combination of two-centre N,H...O and C,H...S hydrogen bonds and a three-centre C,H...(O,S) hydrogen bond. A combination of two-centre N,H...O and C,H...O hydrogen bonds links the molecules of O -ethyl N -(4-methylbenzoyl)thiocarbamate, C11H13NO2S, into chains of rings, which are linked into sheets by an aromatic ,,, stacking interaction. In O,S -diethyl N -(4-methylbenzoyl)imidothiocarbonate, C13H17NO2S, pairs of molecules are linked into centrosymmetric dimers by pairs of symmetry-related C,H...,(arene) hydrogen bonds, while the molecules of O,S -diethyl N -(4-chlorobenzoyl)imidothiocarbonate, C12H14ClNO2S, are linked by a single C,H...O hydrogen bond into simple chains, pairs of which are linked by an aromatic ,,, stacking interaction to form a ladder-type structure. [source] | ||||||||||