192726-05-9

Usage

Chemical Properties

White Solid

InChI:InChI=1/C27H38N4O3/c1-19(2)25(31-15-9-14-29-27(31)34)26(33)30-22(16-20-10-5-3-6-11-20)18-24(32)23(28)17-21-12-7-4-8-13-21/h3-8,10-13,19,22-25,32H,9,14-18,28H2,1-2H3,(H,29,34)(H,30,33)/t22-,23-,24-,25-/m0/s1

Upstream product

• 156732-13-7 (5S)-2-amino-5-dibenzylamino-4-oxo-1,6-diphenylhex-2-ene 
• 1026752-79-3 N-(3-aminopropyl)-N-(methoxycarbonyl)-L-valine 
• 192726-03-7 (S)-(-)-N-carboxymethyl-N(β)cyanoethyl valine 
• 51078-49-0 N-(2-cyanoethyl)-L-valine 
• 72-18-4 L-valine 
• 402712-50-9 N-(2S-(2-oxotetrahydropyrimidin-1-yl)-3-methylbutanoyl)imidazole 
• 156732-15-9 (2S,3S,5S)-2-(N,N-dibenzylamino)-3-hydroxy-5-amino-1,6-diphenylhexane 
• 192725-50-1 (S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid 
• 192800-77-4 2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride 
• 192726-04-8 (2S,3S,5S)-2-N,N-dibenzylamino-3-hydroxy-5-(2S-(2-oxotetrahydropyrimidin-2-yl)-3-methylbutanoyl)amino-1,6-diphenylhexane 

Downstream Products

• 192725-17-0 lopinavir 
• 192726-06-0 (2S,3S,5S)-2-amino-3-hydroxy-5-(2S-(1-tetrahydro-pyrimid-2-onyl)-3-methylbutanoyl)amino-1,6-diphenylhexane (S)-pyroglutamic acid salt 

Relevant academic research and scientific papers

Synthesis and characterization of novel analogues of lopinavir

The present work describes the identification, origin, synthesis, characterization and control of four novel analogues of lopinavir viz. leucine analogue of lopinavir, isoleucine analogue of lopinavir, methyl analogue of lopinavir and dihydroxy analogue of lopinavir.

Design and synthesis of HIV-1 protease inhibitors incorporating oxazolidinones as P2/P2′ ligands in pseudosymmetric dipeptide isosteres

A series of novel HIV-1 protease inhibitors based on two pseudosymmetric dipeptide isosteres have been synthesized and evaluated. The inhibitors were designed by incorporating N-phenyloxazolidinone-5-carboxamides into the hydroxyethylene and (hydroxyethyl)hydrazine dipeptide isosteres as P2 and P2′ ligands. Compounds with (S)-phenyloxazolidinones attached at a position proximal to the central hydroxyl group showed low nM inhibitory activities against wild-type HIV-1 protease. Selected compounds were further evaluated for their inhibitory activities against a panel of multidrug-resistant protease variants and for their antiviral potencies in MT-4 cells. The crystal structures of lopinavir (LPV) and two new inhibitors containing phenyloxazolidinone-based ligands in complex with wild-type HIV-1 protease have been determined. A comparison of the inhibitor-protease structures with the LPV-protease structure provides valuable insight into the binding mode of the new inhibitors to the protease enzyme. Based on the crystal structures and knowledge of structure-activity relationships, new inhibitors can be designed with enhanced enzyme inhibitory and antiviral potencies.

Processes and intermediates for preparing retroviral protease inhibitors

The instant invention provides processes and intermediates employed in the synthesis of ((2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)-amino-3-hydroxy-5-(2S-(1-tetrahydropyrimid-2-onyl)-3-methyl-butanoyl)amino-1,6-diphenylhexane and analogs thereof.

Retroviral protease inhibiting compounds

A compound comprising a substituent of the formula (II) is disclosed as an HIV protease inhibitor. Intermediates for making such compounds and processes for making such intermediates are also disclosed.