56979-29-4

Upstream product

• 1026430-54-5 C₂₉H₃₁NO₇ 
• 86827-18-1 N-benzyloxycarbonyl-O-benzyl-L-tyrosine 

Downstream Products

• 1026588-95-3 [(1S,2S)-1-(4-Benzyloxy-benzyl)-3-chloro-2-hydroxy-propyl]-carbamic acid benzyl ester 
• 162541-31-3 [(S)-2-(4-Benzyloxy-phenyl)-1-(S)-oxiranyl-ethyl]-carbamic acid benzyl ester 
• 162538-16-1 {(1S,2R)-1-(4-Benzyloxy-benzyl)-3-[((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-(2-trimethylsilanyl-ethoxycarbonyl)-amino]-2-hydroxy-propyl}-carbamic acid benzyl ester 
• 162538-17-2 [(2R,3S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-(4-hydroxy-phenyl)-butyl]-((2R,3S)-3-tert-butoxycarbonylamino-2-hydroxy-4-phenyl-butyl)-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 162538-15-0 {(1S,2R)-1-Benzyl-3-[(2R,3S)-3-benzyloxycarbonylamino-4-(4-benzyloxy-phenyl)-2-hydroxy-butylamino]-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 162536-43-8 {(1S,2R)-3-[[(2R,3S)-3-Amino-2-hydroxy-4-(4-hydroxy-phenyl)-butyl]-(2-trimethylsilanyl-ethoxycarbonyl)-amino]-1-benzyl-2-hydroxy-propyl}-carbamic acid tert-butyl ester 
• 162539-57-3 {(S)-3-((S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butylamino)-2-hydroxy-1-[4-(2-pyridin-2-yl-ethoxy)-benzyl]-propyl}-carbamic acid tert-butyl ester 
• 162539-95-9 {(S)-3-((S)-3-tert-Butoxycarbonylamino-2-hydroxy-4-phenyl-butylamino)-2-hydroxy-1-[4-(2-methoxy-ethoxy)-benzyl]-propyl}-carbamic acid tert-butyl ester 

Relevant academic research and scientific papers

Aminodiol HIV protease inhibitors. Synthesis and structure - Activity relationships of P1/P1′ compounds: Correlation between lipophilicity and cytotoxicity

A series of novel aminodiol inhibitors of HIV protease based on the lead compound 1 with structural modifications at P1′ were synthesized in order to reduce the cytotoxicity of 1. We have observed a high degree of correlation between the lipophilicity and the cytotoxicity of this series of inhibitors. It was found that appropriate substitution at the para position of the P1′ phenyl group of 1 resulted in the identification of equipotent (both against the enzyme and in cell culture) compounds (101, 10m, 10n, and 15c) which possess significantly decreased cytotoxicity.

Aminodiol HIV Protease Inhibitors. 1. Design, Synthesis, and Preliminary SAR

A series of HIV protease inhibitors containing a novel C2 symmetrical "aminodiol" core structure were prepared from amino acid starting materials.The ability of the aminodiols to inhibit HIV replication in cell culture is comparable to their ability to inhibit the isolated enzyme, a result compatible with good cell membrane penetration by this class of compounds.Optimization of the structure-activity in this series led to aminodiol 9a (Ki = 100 nM; ED50(HIV-1) = 80 nM) containing P1/P1' benzyl and P2/P2' Boc substituents.Compound 9a is a selective inhibito r of HIV protease versus other aspartyl proteases such as human renin, human cathepsin D, and porcine pepsin.In addition, 9a is equipotent against HIV-1 and HIV-2 in cell culture and demonstrates similar activity in infected T-lymphocytes and PBMCs.After iv and oral administration in rats, 9a displayed significant oral bioavailability (ca. 40percent) and a promising plasma elimination half-life (4 h).