321434-78-0

Basic information

• Product Name: 5,5-dimethyl-4-(2-methyl-benzylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester
• Synonyms: 5,5-dimethyl-4-(2-methyl-benzylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester
• CAS NO: 321434-78-0
• Molecular Weight: 364.509
• Mol File: 321434-78-0.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 5,5-dimethyl-4-(2-methyl-benzylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 5,5-dimethyl-4-(2-methyl-benzylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester(321434-78-0)
• EPA Substance Registry System: 5,5-dimethyl-4-(2-methyl-benzylcarbamoyl)-thiazolidine-3-carboxylic acid tert-butyl ester(321434-78-0)

Safety Data

• Hazardous Substances Data: 321434-78-0(Hazardous Substances Data)

Upstream product

• 72778-00-8 (R)-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 
• 1113-41-3 L-penicillamine 
• 89-93-0 ortho-methylbenzylamine 
• 117918-23-7 (R)-3-tert-butoxycarbonyl-5,5-dimethyl-1,3-thiazolidine-4-carboxylic acid 

Downstream Products

• 1054648-28-0 acetic acid 3-{(1S,2S)-1-benzyl-3-[(4R)-5,5-dimethyl-4-(2-methyl-benzylcarbamoyl)-thiazolidin-3-yl]-2-hydroxy-3-oxo-propylcarbamoyl}-2-methyl-phenyl ester 
• 186538-00-1 (R)-N-(2-methylbenzyl)-3-[(2S,3S)-2-hydroxy-3-[3-hydroxy-2-methylbenzoyl]amino-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 
• 478699-59-1 Boc-Apns-Dmt-NH(o-methylbenzyl) 
• 186538-15-8 (R)-N-(2-methylbenzyl)-3-[(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoyl]-5,5-dimethyl-1,3-thiazolidine-4-carboxamide 

Relevant articles and documents

Structure-activity relationships of novel HIV-1 protease inhibitors containing the 3-amino-2-chlorobenzoyl-allophenylnorstatine structure

A series of peptidomimetic human immunodeficiency virus (HIV) protease inhibitors containing substituted allophenylnorstatine (Apns: (2S,3S)-3-amino-2-hydroxy-4-phenylbutyric acid) were designed and synthesized. From the structure-activity relationship of this series of compounds, SM-309515 was found to have potent antiviral activity against wild-type and resistant HIV-1s and to possess a desirable pharmacokinetic profile in dogs.

Structure-activity relationship of small-sized HIV protease inhibitors containing allophenylnorstatine

We designed and synthesized a new class of peptidomimetic human immunodeficiency virus (HIV) protease inhibitors containing a unique unnatural amino acid, allophenylnorstatine [Apns; (2S,3S)-3-amino-2-hydroxy- 4-phenylbutyric acid], with a hydroxymethylcarbonyl (HMC) isostere as the active moiety. A systematic evaluation of structure - activity relationships for HIV protease inhibition, anti-HIV activities, and pharmacokinetic profiles has led to the delineation of a set of structural characteristics that appear to afford an orally available HIV protease inhibitor. Optimum structures, exemplified by 21f (JE-2147), incorporated 3-hydroxy-2- methylbenzoyl groups as the P2 ligand, (R)-5,5-dimethyl-1,3-thiazolidine-4- carbonyl (Dmt) residue at the P1' site, and 2-methylbenzylcarboxamide group as the P2' ligand. The present study demonstrated that JE-2147 has potent antiviral activities in vitro and exhibits good oral bioavailability and plasma pharmacokinetic profiles in two species of laboratory animals.