Diastereoselective syn-epoxidation of 2-alkyl-4-enamides to epoxyamides: Synthesis of the Merck HIV-1 protease inhibitor epoxide intermediate

(1R,2S)-(+)-cis-1-Amino-2-indanol: An Effective Ligand for Asymmetric Catalysis of Transfer Hydrogenations of Ketones

“…In order to maximize asymmetric inductions, we felt that the use of a stereochemically rigid amino alcohol, and in particular, (1 R ,2 S )-(+)- cis -1-amino-2-indanol ( 1 ), would be beneficial. Amino alcohol 1 , which is commercially available in both enantiomeric forms, is an important component of the Merck anti-HIV compound Indinavir and has been used as the basic component of a valuable series of oxazolidinone chiral auxiliaries and bis-oxazolines for asymmetric catalysis of Diels−Alder reactions …”

Quantitative Structure-Activity Relationship of some HIV-1 Protease Inhibitors: A Fujita-Ban Type Analysis

“…"~~ to identify two compounds (3) (A-77003) and (4) (A-80987), possessing adequate anti-HN activity; of these two, A-80987 was found to possess better oral bioavailability in both animal models and in humans? Further studies on the analogues of A-80987 (b7) led to the development of ritonavir (ABT-538) (8) which possesses high oral bioavailability in both animals and humans and a substantially reduced rate of metabolism?.l6 For further investigation, the analogues of ritonavir (9) were also studied. 16 We present here a more systematic and quantitative study on the structure-activity relationships of various analogues of A-80987 (5-7) and those of ritonavir (9) in order to investigate the possibility of designing still better analogues.…”

Molecular Modeling of Anti HIV Drugs of Protease Inhibitor Group by CoMFA

“…In this sequence several non peptidic inhibitors were also prepared that could bind with the enzyme. Since the clinical development of peptide-derived compound has been hindered by their poor pharmacokinetics, including low oral bioavailability and rapid excretion [6,7] therefore, we have focused ourselves on discussing the derivable by 3D QSAR studies on both peptidic and non peptidic inhibitors by CoMFA (Comparative Molecular Field Analysis). The hydrophobicity (P) of a drug is critical to how easily it crosses cell membranes and may also be important in receptor interaction [8,9].…”