129491-64-1Relevant academic research and scientific papers
A short approach to the synthesis of the ritonavir and lopinavir core and its C-3 epimer via cross metathesis
Ramu, Errabelli,Venkateswara Rao
experimental part, p. 2201 - 2204 (2010/03/04)
A short synthesis of hydroxyethylene dipeptide isostere, a core unit of the HIV-protease inhibitors ritonavir and lopinavir, its C-3 epimer and C2 symmetric diamino diol is described. The crucial aspects of the synthesis are self-cross metathesis and exploitation of C2-symmetric of the metathesis product 8 to obtain the required skeleton.
Design, synthesis, evaluation, and crystallographic-based structural studies of HIV-1 protease inhibitors with reduced response to the V82A mutation
Clemente, José C.,Robbins, Arthur,Gra?a, Paula,Paleo, M. Rita,Correa, Juan F.,Villaverde, M. Carmen,Sardina, F. Javier,Govindasamy, Lakshmanan,Agbandje-McKenna, Mavis,McKenna, Robert,Dunn, Ben M.,Sussman, Fredy
, p. 852 - 860 (2008/09/20)
In our quest for HIV-1 protease inhibitors that are not affected by the V82A resistance mutation, we have synthesized and tested a second generation set of C2-symmetric HIV-1 protease inhibitors that contain a cyclohexane group at P1 and/or P1′
Facile and highly stereoselective synthesis of the C2-symmetrical diamino diol core-unit of HIV-1 protease inhibitors and of their symmetrical and unsymmetrical analogs from lithiated 2-(dibenzylamino)alkyl carbamates: Oxidative dimerization
Weber,Kolczewski,Fr?hlich,Hoppe
, p. 1593 - 1606 (2007/10/03)
The lithio derivatives of (S)-and (R)-2-(N,N-dibenzylamino)alkyl carbamates 3 and ent-3, generated by substrate-directed deprotonation from the precursors 2 and ent-2, add with high diastereoselectivity to (S)-2-(N,N- dibenzylamino)alkanals. The (S)-aminoaldehyde 5a, derived from (S)- phenylalanine, is produced in situ from the lithium compound 3a by the controlled addition of dioxygen to the reaction mixture affording the protected anti,syn,anti-α,δ-diamino-β,γ-diol 6aa which is the core unit of anti-HIV 1 protease agents. Several symmetric and unsymmetric structure analogs, differing in the substitution pattern and the configurations, have been synthesized. A further approach to the title compound is given by the acylation of lithium derivatives 3/4, followed by a hydride reduction. The reaction of the lithium derivatives 3a/4a with CuCl leads to an eliminative oxidative coupling with formation of (3 E/Z, 2S,5S)-2,5-dibenzylamino-1,6- diphenylhex-3-enes (E)- and (Z)-26.
Synthesis of novel C2-symmetric and pseudo C2-symmetric based diols, epoxides and dideoxy derivatives of HIV protease inhibitors
Gurjar, Mukund K.,Pal, Shashwati,Rama Rao,Pariza, Richard J.,Chorghade, Mukund S.
, p. 4769 - 4778 (2007/10/03)
The Julia's olefination reaction between the sulfone derivative (10) and the aldehyde (13) (both obtained from L-phenylalanine) followed by debenzylation led to the formation (2S,5S,3E)-2,5-bis-[(1,1-dimethyl ethoxy)-carbonyl]amino-1,6-diphenylhex-3-ene (
Synthesis of a novel C2-symmetrical (2S,5S)-2,5-bis-[(1,1 -dimethylethoxy) carbonylamino]-1,6-diphenylhex-3-ene: Applications in the synthesis of potential HIV protease inhibitors
Rama Rao
, p. 2505 - 2508 (2007/10/02)
The synthesis of a novel and versatile (2S,5S)-2,5-bis-[(1,1′-dimethylethoxy)carbonylamino]-1,6-diphenylhex-3-ene (2) based on Julia's olefination strategy coupled with its application in stereoselective preparations of HIV protease inhibitors has been discussed.
Stereocontrolled Synthesis of C2-Symmetric and Pseudo-C2-Symmetric Diamino Alcohols and Diols for Use in HIV Protease Inhibitors
Kempf, Dale J.,Sowin, Thomas J.,Doherty, Elizabeth M.,Hannick, Steven M.,Codavoci, LynnMarie,et al.
, p. 5692 - 5700 (2007/10/02)
The stereocontrolled syntheses of dibenzyldiamino alcohol 1 and dibenzyldiamino diols 2-4, core units of potent C2-symmetric and pseudo-C2-symmetric inhibitors of HIV protease, are described, starting from phenylalanine.Stereoselecti
