192725-56-7

Basic information

• Product Name: ((1S,2S,4S)-4-Amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester
• CAS NO: 192725-56-7
• Molecular Weight: 440.539
• Mol File: 192725-56-7.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: ((1S,2S,4S)-4-Amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester(CAS DataBase Reference)
• NIST Chemistry Reference: ((1S,2S,4S)-4-Amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester(192725-56-7)
• EPA Substance Registry System: ((1S,2S,4S)-4-Amino-1-benzyl-2-hydroxy-5-phenyl-pentyl)-carbamic acid (3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl) ester(192725-56-7)

Safety Data

• Hazardous Substances Data: 192725-56-7(Hazardous Substances Data)

Upstream product

• 192725-55-6 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl-(4-nitrophenyl)carbonic acid 
• 162119-35-9 3-acetoxy-(3R,3αS,6αR)-bis-tetrahydrofuran 
• 156928-09-5 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol 
• 186488-54-0 (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-yl 4-nitrophenyl carbonate 
• 186487-62-7 {(1S,3S,4S)-1-Benzyl-4-[(3R,3aS,6aR)-(hexahydro-furo[2,3-b]furan-3-yl)oxycarbonylamino]-3-hydroxy-5-phenyl-pentyl}-carbamic acid tert-butyl ester 

Relevant articles and documents

Synthesis and SAR studies of potent HIV protease inhibitors containing novel dimethylphenoxyl acetates as P2 ligands

Isopropyl substituted 4-thioazolyl valine side chains are highly optimized P2-P3 ligands for C2 symmetry-based HIV protease inhibitors, as exemplified by the drug ritonavir. Replacement of the side chain with the conformationally constrained hexahydrofurofuranyloxy P2 ligand in combination with a dimethylphenoxyacetate on the other end of the ritonavir core diamine yielded highly potent HIV protease inhibitors. The in vitro antiviral activity in MT4 cells increased by 10- and 20-fold, respectively, in the absence and presence of 50% human serum compared to ritonavir. The structure-activity relationships of inhibitor series with this combination of ligands were investigated. Preliminary pharmacokinetic studies in rats indicated rapid elimination of the inhibitors from the blood, and the plasma levels were not significantly enhanced by coadministration with ritonavir. However, the novel structural features and the high intrinsic antiviral potency of this series provides potential for the future exploration of prodrug strategies.