126456-36-8Relevant articles and documents
Allyltrichlorostannane additions to α-amino aldehydes: Application to the total synthesis of the aspartyl protease inhibitors L-682,679, L-684,414, L-685,434, and L-685,458
Dias, Luiz C.,Diaz, Gaspar,Ferreira, Andrea A.,Meira, Paulo R. R.,Ferreira, Edílson
, p. 603 - 622 (2007/10/03)
The hydroxyethylene dipeptide isosteres L-682,679, L-684,414, L-685,434, and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-amino aldehyde, followed by hydroboration of the corresponding 1,2-
Short total synthesis of aspartyl protease inhibitors L-685,434, L-682,679 and L-685,458
Dias, Luiz C.,Ferreira, Andrea A.,Diaz, Gaspar
, p. 1845 - 1849 (2007/10/03)
Hydroxyethylene dipeptide isosteres L-685,434, L-682,679 and L-685,458 were synthesized in a few steps by a sequence involving an allyltrichlorostannane coupling with an α-aminoaldehyde followed by hydroboration of the corresponding 1,2-syn and 1,2-anti a
HIV protease inhibitors useful for the treatment of aids
-
, (2008/06/13)
Compounds of the form,ψ ψ A-G-Jψ ψ wherein A is an amine protecting group or urethane, G a dipeptide isostere and J a small terminal group are described. They are distinguished by tetrahydrofuryl or tetrahydropyranyl substituents, and the like. 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 ingredients, whether or not in combination with other antivirals, immunomodulators, antibiotics or vaccines. Methods of treating AIDS and methods of preventing or treating infection by HIV are also described.ψ
HIV-1 protease inhibitors based on hydroxyethylene dipeptide isosteres: An investigation into the role of the P1' side chain on structure-activity
Young,Payne,Thompson,Gaffin,Lyle,Britcher,Graham,Schultz,Deana,Darke,Zugay,Schleif,Quintero,Emini,Anderson,Huff
, p. 1702 - 1709 (2007/10/02)
A systematic investigation was undertaken to determine the role of the P1' sidechain in a series of hydroxyethylene isostere based inhibitors of HIV-1 protease. Substitution and homologation of the benzyl P1' side chain of the Phe-Phe isostere based pseudo peptides 1 (L-682,679) and 2 (L-685,434) with various heteroalkyl groups leads to a series of extremely potent inhibitors of the enzyme. Several examples of the most potent inhibitors were very effective in an ex vivo cell based viral spread assay using human H9 T- lymphocytes and the IIIb isolate of HIV-1. Compound 19 is 120 times more potent than 1 and 16 times more potent than 2 in inhibiting the spread of infection in this assay.
Highly Diastereoselective Alkylations of Chiral Amide Enolates: New Routes to Hydroxyethylene Dipeptide Isostere Inhibitors of HIV-1 Protease
Askin, D.,Wallace, M. A.,Vacca, J. P.,Reamer, R. A.,Volante, R. P.,Shinkai, I.
, p. 2771 - 2773 (2007/10/02)
The nonchelate enforced chiral amide enolates derived from 4-7 react with alkyl iodide and protected α-amino epoxide electrophiles to produce the HIV protease inhibitors 10 and 16-19 with high diastereoselectivity.