170028-72-5Relevant academic research and scientific papers
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.
Catalytic carbonylation of functionalized diamines: Application to the core structure of DMP 323 and DMP 450
Hylton, Keisha-Gay,Main, A. Denise,McElwee-White, Lisa
, p. 1615 - 1617 (2007/10/03)
W(CO)6-catalyzed carbonylation provides an alternative to phosgene or phosgene derivatives such as 1,1-carbonyldiimidazole (CDI) for the conversion of amines to ureas. As an illustration, the core structure of the HIV protease inhibitors DMP 32
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
Synthesis of unsymmetric cyclic urea diols, a novel class of HIV protease inhibitors
Stone, Benjamin R. P.,Harris, Gregory D.,Cann, Reginald O.,Smyser, Thomas E.,Confalone, Pat N.
, p. 6127 - 6130 (2007/10/03)
Unsymmetric cyclic urea diols of general structure 1 can be prepared either via an isourea derived from the symmetric diamine 2 or by the selective removal of a benzyl group from certain symmetric cyclic ureas 8, employing dissolving metal reduction.
Stereoselective synthesis of HIV-1 protease inhibitor, DMP 323
Pierce,Pierce, Michael E.,Harris,Harris, Gregory D.,Islam,Islam, Qamrul,Radesca,Radesca, Lilian A.,Storace,Storace, Louis,Waltermire,Waltermire, Robert E.,Wat,Wat, Ed,Jadhav,Jadhav, Prabhakar K.,Emmett,Emmett, George C.
, p. 444 - 450 (2007/10/02)
DMP 323, a potent HIV-1 protease inhibitor, has been synthesized by an efficient stereoselective process, amenable to large scale preparations. The core C2 symmetric diol was synthesized by a stereoselective pinacol coupling of CBZ protected D-phenylalanine. Judicious selection of protecting groups allowed cyclic urea formation under mild conditions, enhanced the ease of bis-alkylation, and led te intermediates which were easily purified without chromatography. Additionally, a one-pot, high yield process was developed te prepare the alkylating agent, 4-[(triphenylmethoxy)methyl]benzyl chloride from 1,4-benzenedimethanol.
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 (2007/10/02)
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
