170870-15-2Relevant academic research and scientific papers
A Practical Synthesis of Nonpeptide Cyclic Ureas as Potent HIV Protease Inhibitors
Rossano, Lucius T.,Lo, Young S.,Anzalone, Luigi,Lee, Ying-Chi,Meloni, David J.,et al.
, p. 4967 - 4970 (1995)
The utilization of the oxydimethylene group to form a trioxepane ring for the protection of 1,2-diols was demonstrated.A process starting with natural L-tartaric acid as the chiral building block is utilized in the synthesis of optically active, nonpeptid
Carbonylation of functionalized diamine diols to cyclic ureas: Application to derivatives of DMP 450
Darko, Ampofo K.,Curran, F. Chris,Copin, Chloé,McElwee-White, Lisa
, p. 3976 - 3983 (2011/06/25)
Synthesis of the cyclic urea core structure of the HIV protease inhibitor DMP 450 has been achieved via W(CO)6/I2-catalyzed carbonylation of diamine intermediates. Carbonylations of related functionalized diamines to derivatives of the DMP 450 core structure were also examined. Selected diamine diol substrates could be converted to the cyclic urea core structure by catalytic carbonylation without protection of the diol functionality.
Synthesis, antiviral activity and pharmacokinetics of P1/P1′ substituted 3-aminoindazole cyclic urea HIV protease inhibitors
Kaltenbach III, Robert F.,Patel, Mona,Waltermire, Robert E.,Harris, Gregory D.,Stone, Benjamin R. P.,Klabe, Ronald M.,Garber, Sena,Bacheler, Lee T.,Cordova, Beverly C.,Logue, Kelly,Wright, Matthew R.,Erickson-Viitanen, Susan,Trainor, George L.
, p. 605 - 608 (2007/10/03)
A series of P1/P1′ substituted cyclic urea analogues were prepared in an attempt to increase the intra-cellular antiviral potency of the nonsymmetrical 3-aminoindazoles DMP 850 and DMP 851. The effect of alkyl substitution of the P1/P1′ residues on cellul
C2-Symmetric bisphosphinites and a bisaminophosphine as new chiral ligands for Pd-catalyzed asymmetric allylic substitution
Zhang, Ao,Feng, Yan,Jiang, Biao
, p. 3123 - 3130 (2007/10/03)
A family of C2-symmetric bisphosphinites 3, 5, 7, 9 and bisaminophosphine 11 were prepared and were probed in the prototypical reaction system of palladium-catalyzed asymmetric allylic substitution. The highest ee of 86% was achieved by employi
Grignard addition to aldonitrones. Stereochemical aspects and application to the synthesis of C2-symmetric diamino alcohols and diamino diols
Dondoni, Alessandro,Perrone, Daniela,Rinaldi, Marilisa
, p. 9252 - 9264 (2007/10/03)
A new example of the stereoselective installation of the amino group at a saturated carbon center via organometallic addition of chiral aldehydes to nitrones is illustrated by the synthesis of 1,3-diamino propanol 1 and 1,4- diamino butandiol 2 units. Three diamino alcohol 1 stereotriads were obtained by stereoselective addition of alkylmagnesium halides (benzyl, cyclohexylmethyl, and metallyl) to the N-benzyl nitrones derived from β- amino-α-hydroxy aldehydes followed by reduction of the resulting N- benzylhydroxylamines. Three 1,4-dibenzyl substituted stereoisomers of type 2 with fixed S configuration at C2 and C3 were prepared by sequential and simultaneous amination in two directions starting from L-threose nitrone and L-tartraldehyde bis-nitrone, respectively. The R,S,S,R isomer obtained by the former route was converted into a seven-membered ring cyclic urea (1,3- diazapin-2-one), i.e., a compound that belongs to a class of nonpeptide HIV- 1 protease inhibitors.
Stereoisomers of cyclic urea HIV-1 protease inhibitors: Synthesis and binding affinities
Kaltenbach III,Nugiel,Lam,Klabe,Seitz
, p. 5113 - 5117 (2007/10/03)
We have synthesized stereoisomers of cyclic urea HIV-1 protease inhibitors to study the effect of varying configurations on binding affinities. Four different synthetic approaches were used to prepare the desired cyclic urea stereoisomers. The original cy
SUBSTITUTED BICYCLIC PHOSPHORAMIDES AND DERIVATIVES THEREOF
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, (2008/06/13)
This invention relates to substituted bicyclic phosphoramides and derivatives thereof, useful as retroviral protease inhibitors and as standards and reagents in determining the ability of a potential pharmaceutical to inhibit viral replication or HIV protease, to pharmaceutical compositions comprising such compounds, and to methods of using these compounds for treating viral infection.
Novel bicyclic phosphordiamidate HIV protease inhibitors
Smallheer, Joanne M.,Seitz, Steven P.
, p. 2367 - 2376 (2007/10/03)
Several substituted (3-endo,4-endo,6-exo)-8-oxa-7-diaza-1phosphabicyclo[3.2.1]octanols were prepared and evaluated as inhibitors of HIV protease. This new bicyclic ring system is the product of an unexpected intramolecular cyclization observed upon base t
Method for preparing cyclic sulfamides and their use for the synthesis of HIV protease inhibitors
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, (2008/06/13)
The present invention discloses processes for the preparation of substituted cyclic sulfamides which are useful as intermediates for the synthesis of cyclic sulfamide human immunodeficiency virus (HIV) protease inhibitors. Such substituted cyclic sulfamid
