[figure: see text] 1,2-Migration and concurrent glycosidation of phenyl 2,3-O-thionocarbonyl-1-thlo-alpha-L-rhamnopyranosides under the action of methyl trifluoromethanesulfonate (MeOTf) afforded in high yields the 3-O-(methylthio)carbonyl-2-S-phenyl-2,6-dideoxy-beta-L-glucopyranosides, ready precursors to the corresponding 2-deoxy-beta-glycosides.

ETHNOPHARMACOLOGICAL RELEVANCE Raphanus sativus seeds (Brassicaceae) known as Raphani Semen have long been used as anti-cancer and/or anti-inflammatory agents in Korean traditional medicine. This study was designed to isolate the bioactive constituents from the seed extracts of Raphanus sativus and evaluate their anti-inflammatory and antitumor activities. MATERIAL AND METHODS Bioassay-guided...

Cyclocondensation of 2-[bis(methylthio)methylene]malononitrile (1) and cysteamine (2) afforded 2-(thiazolidin-2-ylidene)malononitrile (3). This compound on treatment with NaSH gave the corresponding thioamide derivative 4a in a regioselective manner on the basis of its single crystal X-ray diffraction analysis. Reaction of this compound with several alpha-bromocarbonyl compounds gave new 2-(E)-...

A scaleable synthetic route is described to obtain 2-(4-acetylpiperadin-1-yl)-6-[3,5-bis(trifluoromethyl)phenylmethyl]-4-(2-methylphenyl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-b][1,5]oxazocin-5-one (1, KRP-103) as a neurokinin (NK)(1) antagonist. The key step in the synthesis is the intramolecular cyclization of N-[3,5-bis(trifluoromethyl)phenylmethyl]-N-(3-hydroxypropyl)-4-chloro-6-(2-methylpheny...

Synthesis of the model compounds of carzinophilin carrying 2-methylidene-1-aza-bicyclo[3.1.0]hexane systems was achieved. Formation of malonylidenes or N-acyl-glycinylidenepyrrolidines was carried out by utilizing Eschenmoser’s sulfide contraction or Herdeis’s condensation between the 2-methylthio-D-pyrrolone derivatives and ethyl nitroacetate, respectively. The 1-azabicyclo-[3.1.0]hexane syste...

New N-(benzyl carbamothioyl)-2-hydroxy substituted benzamides 13, 20, and 21 were synthesized using sodium bicarbonate and benzyl amine with 2-thioxo-substituted-1,3-benzoxazines 6, 10a, b, 11c, and 12a-n. The 2-thioxo-substituted-1,3-oxazines 6, 10a-b, 11d 12a-n, and 26 were converted to the corresponding 2-methylthio-substituted-1,3-oxazines 14a-l and 24 which were then converted to 2-benzyl ...