65838-17-7Relevant academic research and scientific papers
CYTOCHROME P450 OXIDASE INHIBITORS AND USES THEREOF
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Page/Page column 109, (2008/06/13)
The present invention features compounds of formula I or pharmaceutically acceptable salts, solvates or prodrugs thereof, and methods of using the same to inhibit the metabolizing activities of CYP enzymes. The present invention also features methods of using these compounds, salts, solvates or prodrugs to improve the pharmacokinetics of drugs that are metabolized by CYP enzymes.
A highly flexible route to 1,2,3,4,5,6-hexahydro-5-hydroxypyrimidin-2-ones as potential HIV protease inhibitors
Enders, Dieter,Wortmann, Lars,Raabe, Gerhard,Duecker, Barbara
, p. 559 - 581 (2007/10/03)
The first asymmetric synthesis of potential HIV protease inhibitors of type II, III and IV is described. Key step of the synthesis is an auxiliary based stereoselective alkylation by means of the (R)-1-amino-2-methoxymethylpyrrolidine (RAMP)- / (S)-1-amino-2-methoxymethylpyrrolidine (SAMP)-hydrazone method starting from a readily available key building block, pyrimidin-2,5-dione (6). The synthesis is short and highly versatile in the choice of the substitution pattern as well as the absolute configuration of the alkylated 1,2,3,4,5,6-Hexahydro-5-hydroxypyrimidin-2-ones.
New anti-HIV derivatives: Synthesis and antiviral evaluation
De Michelis,Rocheblave,Priem,Chermann,Kraus
, p. 1253 - 1262 (2007/10/03)
A small focused library of 18 compounds incorporating the motif 1,3-(N,N'-dibenzyl)diamino-2-propanol has been synthesized, using adapted synthetic methodologies. These series of compounds were evaluated for their in vitro anti-HIV activity on infected MT4 cells (syncytium formation observation). Some of the new synthesized compounds show potent anti-HIV activities. EC50 values for compounds (31, 40, 34, 37 and 46Scheme 3(i) Na2SO4, CH2Cl2, rt; (ii) NaBH4, EtOH, 0°C; (iii) Boc2O, CH2Cl2, 0°C; (iv) DMSO, TFAA, Et3N, CH2Cl2, -60°C; (v) TFA, CH2Cl2, rt; (vi) BOP, RCOOH, Et3N, CH2Cl2, rt.) range from 0.1 to 1μM. In order to determine at which level these new derivatives interfere with the HIV replicative cycle, inhibition assays on recombinant HIV protease and HIV integrase have been performed. None of the compounds were found active on these two enzymatic targets. Experiments are in progress in order to identify their biological target within the HIV replicative cycle. Copyright (C) 2000 Elsevier Science Ltd.
Synthesis and anti-HIV activity of α-thiophenoxy-hydroxyethylamide derivatives
Medou, Martial,Priem, Ghislaine,Rocheblave, Luc,Pepe, Gerard,Meyer, Monique,Chermann, Jean-Claude,Kraus, Jean-Louis
, p. 625 - 638 (2007/10/03)
A series of new anti-HIV derivatives containing a novel α- thiophenoxyhydroxyethylamide core have been synthesized, using S- phenylbenzenethiosulfonate as the thiosulfenylating reagent. Some of the new synthesized compounds (1a, 1c, 1g, 1i, 1j and 1l) inhibited HIV replication in cell culture assays (syncytia formation) with effective concentrations (EC50) ranging from 0. 1-1 μM. Incorporation of thiophenoxy substitution within various pseudomimetic peptide backbones provided a series of highly potent HIV inhibitors.
Asymmetric synthesis of 1,2,3,4,5,6-hexahydro-5-hydroxypyrimidin-2-ones as potential HIV-protease inhibitors
Enders, Dieter,Wortmann, Lars,Duecker, Barbara,Raabe, Gerhard
, p. 1195 - 1201 (2007/10/03)
The first asymmetric synthesis of potential cyclic urea HIV protease inhibitors of Type 2 is reported. The synthesis is short and highly versatile in the choice of the substitution pattern and absolute configuration of the products starting from readily available materials. Nonchiral central building block 5 was synthesized and subsequently asymmetrically alkylated under (R)-/(S)-1-amino-2-(methoxymethyl)pyrrolidine (RAMP/SAMP)-auxiliary control to provide 8a-e. The alkylated ketones then were reduced to the target compounds 9a-e, with good-to-excellent overall yields, as well as diastereoisomeric and enantiomeric purities.
Synthesis of new 7-membered α-phenylthio cyclic oxamides: HIV inhibitors
Medou,Priem,Quelever,,Camplo,Kraus
, p. 4021 - 4024 (2007/10/03)
Based on the concept of bioisosterism, we report the computer design and the synthesis of original 7-membered α-phenylthio cyclic oxamides with potent anti HIV-1 properties.
Synthesis and anti-HIV activities of symmetrical N1,N3-dibenzyl-2- hydroxy-propane derivatives
Medou,Bouygues,Rocheblave,Chermann,Kraus
, p. 1861 - 1866 (2007/10/03)
We report the synthesis and the anti-HIV activities of new C2- symmetrical and achiral N1,N3-dibenzyl-2-hydroxy-propane isosteres. Some of them showed significant inhibitory activity with respect to HIV-infected MT4 cells
