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At least 109 records · Page 6Linked to original sources
PubMed2005

Synthesis of 6,19-sulfamidate bridged pregnanes.

Conformationally restrained substituted pregnane-20-one derivatives were obtained by an intramolecular nitrene addition onto a C-5/C-6 double bond involving a tethered C-19 sulfamoyl moiety. The resulting aziridine underwent regioselective nucleophilic ring opening at C-5 at room temperature with cyanide, fluoride, and acetate. In the isolated case of acetate, a reversal of regioselectivity was observed at higher temperatures, a result attributed to a rearrangement process involving aziridine ring opening at the C-5 position and subsequent migration of the acetyl moiety to C-6.

Bridged-Ring Compounds↗
PubMed2004

Synthesis and characterization of 9-[P-(N, N-dipropyl sulfamide)] benzoylamino-1,2,3,4-4H-acridine--a potential prodrug for the CNS delivery of tacrine.

9-[P-(N,N-dipropylsulfamide)]benzoylamino-1,2,3,4-4H-acridine (PTHA) was synthesized as a prodrug to improve the curative effect of tacrine hydrochloride (THA), to prolong the activation time in brain, and to decrease the hepatic toxicity. The prodrug was prepared by attaching carboxyl group of probenecid to 9-amino group of THA. The structure of PTHA was confirmed by IR, HNMR, MS and UV. The physiochemical properties and stabilities of the prodrug under various conditions were investigated. Possibility of the prodrug passing through the blood-brain barrier (BBB) was evaluated in vitro by biopartition micellar chromatography (BMC). The concentrations of THA and PTHA in various tissues were determined by reversed-phase high-performance liquid chromatography after intravenous (i.v.) administration. The results showed PTHA was stable in various pHs and temperatures. It was indicated by partition coefficient in ethyl acetate/water that lipophilicity of the prodrug increased and it was predicted by BMC that the prodrug could improve the infiltration ability across BBB of THA. In-vivo experiment showed the concentrations of THA in brain and liver kept stable for about 4 h, which was beneficial for the treatment of Alzheimer's disease (AD). Compared with THA at the same time, AUC in liver decreases significantly, the overall targeting efficiency (TE) was enhanced from 10.97 to 16.11% and AUC(brain)/AUC(liver) increased from 1.52 to 2.53, which suggests the possibility to reduce the hepatic toxicity of THA by the way of the prodrug.

Acridines↗
PubMed2004

Pharmacomodulation of a sulfamide 5-HT6 receptor ligand.

A series of N-omega-aminoalkyl- or N-omega-amidinoalkyl-2,4,6-triisopropyl benzenesulfonamides has been synthesized and their respective affinity indices on 5-HT6 receptor determined. This evaluation clearly showed that the compounds possessing an arylpiperazine moiety or an amidine function exhibited good affinity for the model.

Drug Design↗
PubMed2002

Sulfamide antifolates inhibiting thymidylate synthase: synthesis, enzyme inhibition and cytotoxicity.

Synthesis and biological evaluation are described of seven new analogues (3-9) of two potent thymidylate synthase inhibitors, 10-propargyl-5,8-dideazafolate (1) and its 2-methyl-2-deamino congener ICI 198583 (2). While the new compunds 3 and 4 were analogues of 1 and 2, respectively, containing a p-aminobenzenesulfonyl residue in place of the p-aminobenzoic acid residue, the remaining 5 new compounds were analogues of 4 with the L-glutamic acid residue replaced by glycine (5), L-valine (6), L-alanine (7), L-phenylglycine (8) or L-norvaline (9). The new analogues were tested as inhibitors of thymidylate synthases isolated from tumour (Ehrlich carcinoma), parasite (Hymenolepis diminuta) and normal tissue (regenerating rat liver) and found to be weaker inhibitors than the parent 10-propargyl-5,8-dideazafolic acid. Selected new analogues, tested as inhibitors of growth of mouse leukemia L 5178Y cells, were less potent than the parent 10-propargyl-5,8-dideazafolic acid. Substitution of the glutamyl residue in compound 4 with L-norvaline (9) resulted in only a 5-fold stronger thymidylate synthase inhibitor, but a 40-fold weaker cell growth inhibitor.

Animals↗