158941-60-7

Upstream product

• 4587-33-1 N-(tert-butyloxycarbonyl)-L-asparagine p-nitrophenyl ester 
• 184955-18-8 (R)-N-tert-butyl-3-<(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl>-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 159000-71-2 Boc-Apns-Dmt-NHtBu 
• 148983-13-5 (R)-4-tert-Butylcarbamoyl-5,5-dimethyl-thiazolidine-3-carboxylic acid tert-butyl ester 
• 117918-23-7 (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
• 158941-58-3 (R)-N-tert-butyl-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 

Downstream Products

• 792881-10-8 (S)-2-Amino-N¹-[(1S,2S)-1-benzyl-3-((R)-4-tert-butylcarbamoyl-5,5-dimethyl-thiazolidin-3-yl)-2-hydroxy-3-oxo-propyl]-succinamide 
• 141804-42-4 (R)-N-tert-butyl-3-[(2S,3S)-3-[(S)-2-(1-naphthoxyacetyl)aminosuccinamyl]amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 

Relevant academic research and scientific papers

Structure-activity relationship of orally potent tripeptide-based HIV protease inhibitors containing hydroxymethylcarbonyl isostere

We designed and synthesized a new class of peptidomimetic human immunodeficiency virus protease inhibitors containing a unique unnatural amino acid, allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid], with a hydroxymethylcarbonyl isostere as the active moiety. From a structure-activity relationship study of HIV-1 protease inhibition, enzyme selectivity for other aspartyl proteases, the antiviral activity and pharmacokinetics in rats, 24c (KNI-227) and 24d (KNI-272, our first clinical candidate) were found to be selective and orally potent HIV protease inhibitors. Moreover, an improvement of the pharmacokinetic features of KNI-272 provided two long-lasting and highly bioavailable compounds (24g: JE-2178,h: JE-2179).