- Synthesis, structure, and transformations of cyclic glycerol formals
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Glycerol reacts with paraformaldehyde to give a mixture of 4-hydroxymethyl-1,3-dioxolane and 5-hydroxy-1,3-dioxane. Some transformations (alkylation and replacement of the OH groups with the Cl atoms) of the synthesized compounds were performed. The differences in NMR and mass spectra of the corresponding 1,3-dioxolanes and 1,3-dioxanes were revealed and discussed.
- Raskildina,Valiev,Sultanova,Zlotsky
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- HIV PROTEASE INHIBITORS AND METHODS FOR USING
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Compounds that inhibit proteolytic enzymes of Human Immunodeficiency Virus (HIV) are described. Preparation of the inhibitors, pharmaceutical compositions containing them, and uses of the compounds or compositions for the treatment of HIV infections are also described.
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- Flexible cyclic ethers/polyethers as novel P2-ligands for HIV-1 protease inhibitors: Design, synthesis, biological evaluation, and protein-ligand X-ray studies
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We report the design, synthesis, and biological evaluation of a series of novel HIV-1 protease inhibitors. The inhibitors incorporate stereochemically defined flexible cyclic ethers/polyethers as high affinity P2-ligands. Inhibitors containing small ring 1,3-dioxacycloalkanes have shown potent enzyme inhibitory and antiviral activity. Inhibitors 3d and 3h are the most active inhibitors. Inhibitor 3d maintains excellent potency against a variety of multi-PI-resistant clinical strains. Our structure-activity studies indicate that the ring size, stereochemistry, and position of oxygens are important for the observed activity. Optically active synthesis of 1,3-dioxepan-5-ol along with the syntheses of various cyclic ether and polyether ligands have been described. A protein-ligand X-ray crystal structure of 3d-bound HIV-1 protease was determined. The structure revealed that the P2-ligand makes extensive interactions including hydrogen bonding with the protease backbone in the S2-site. In addition, the P2-ligand in 3d forms a unique water-mediated interaction with the NH of Gly-48.
- Ghosh, Aran K.,Gemma, Sandra,Baldridge, Abigail,Wang, Yuan-Fang,Kovalevsky, Andrey Yu.,Koh, Yashiro,Weber, Irene T.,Mitsuya, Hiroaki
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experimental part
p. 6021 - 6033
(2009/10/23)
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- Cleavage of MEM ethers by tetrahalozincate reagents
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A modification of the zinc halide-mediated removal of the MEM group is described. By the expedient of adding two molar equivalents of ethereal hydrogen chloride or of lithium halide, the method is extended to substrates which otherwise chelate the zinc reagent without undergoing deprotection. The compatibility of the resulting reagent Systems with other functional groups is demonstrated, and examples are presented where deprotection of mono-MEM-protected 1,2- and 1,3-diols can be carried out, avoiding the cyclisation which occurs normally.
- Herbert, John M.,Knight, Julian G.,Sexton, Brian
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p. 15257 - 15266
(2007/10/03)
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- 5-Benzyloxy-1,3-dioxanes
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Herbicidal compositions containing compounds of the formula STR1 where R2 is hydrogen, hydrocarbyl or substituted hydrocarbyl radical; R2a is hydrogen or methyl and R2 and R2a may together form a ring; R5 is hydrogen, alkyl, haloalkyl or cyanoalkyl; Rr is aryl, substituted aryl or heterocyclyl.
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