168899-60-3Relevant articles and documents
HIV protease inhibitors
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, (2008/06/13)
Oligopeptide analogs are described. These compounds are useful in the inhibition of HIV protease, the prevention or treatment of infection by HIV and the treatment of AIDS, either as compounds, pharmaceutically acceptable salts, pharmaceutical composition
Synthesis of the HIV-proteinase inhibitor Saquinavir: A challenge for process research
Goehring, Wolfgang,Gokhale, Surendra,Hilpert, Hans,Roessler, Felix,Schlageter, Markus,Vogt, Peter
, p. 532 - 537 (2007/10/03)
The task of process research, namely developing efficient, economically and technically as well as ecologically feasible syntheses in time, is demonstrated on the HIV-proteinase inhibitor Saquinavir (1), a complex molecule comprising six stereo-centres. Based on the first 26-step research synthesis furnishing a 10% overall yield, process research established a new, short 11-step synthesis affording a 50% overall yield.
Asymmetric synthesis of optically active decahydroisoquinolines useful in HIV-1 protease inhibitor synthesis
Trova, Michael P.,McGee Jr., Kevin F.
, p. 5951 - 5954 (2007/10/02)
An efficient synthesis of amino acid ester 8 is described featuring an asymmetric aza-Diels-Alder reaction of diene 5 and chiral imine 6 which establishes the asymmetry at C-3. Hydrogenation of 7 provides 8 with the desired asymmetry at C-4a and C-8a.
Method for producing 2-isoquinoline compounds
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, (2008/06/13)
1,2,3,4-Tetrahydro-2-isoquinoline-derivatives of the formula STR1 wherein R signifies hydroxy, lower alkylamino, lower alkoxy or phenyl-C2-6 -alkoxy which can carry one or more lower alkyl or lower alkoxy substituents on the phenyl ring, can be
Towards the synthesis of HIV-protease inhibitors. Synthesis optically pure 3-carboxyl-decahydroisoquinolines
Houpis, Ioannis N.,Molina, Audrey,Reamer, Robert A.,Lynch, Joseph E.,Volante,Reider, Paul J.
, p. 2593 - 2596 (2007/10/02)
The synthesis of optically pure decahydroisoquinoline 1, a component of HIV-protease inhibitors, was accomplished in 30-33% overall yield from the readily available optically pure monoacid 4.
A Series of Potent HIV-1 Protease Inhibitors Containing a Hydroxyethyl Secondary Amine Transition State Isostere: Synthesis, Enzyme Inhibition, and Antiviral Activity
Tucker, Thomas J.,Lumma, William C.,Payne, Linda S.,Wai, Jenny M.,Solms, S. Jane de,et al.
, p. 2525 - 2533 (2007/10/02)
A series of HIV-1 protease inhibitors containing a novel hydroxyethyl secondary amine transition state isostere has been synthesized.The compounds exhibit a strong preference for the (R) stereochemistry at the transition state hydroxyl group.Molecular modeling studies with the prototype compound 11 have provided important insights into the structural requirements for good inhibitor-active site binding interaction.N-Terminal extension of 11 into the P2-P3 region led to the discovery of 19, the most potent enzyme inhibitor in the series (IC50 = 5.4 nM). 19 was shown to have potent antiviral activity in cultured MT-4 human T-lymphoid cells.Comparison of analogs of 19 with analogs of 1 (Ro31-8959) demonstrates that considerably different structure-activity relationships exist between these two subclasses of hydroxyethylamine HIV-protease inhibitors.
