17224-88-3

Upstream product

• 3182-95-4 L-Phenylalaninol 
• 2578-84-9 N-benzyloxycarbonyl-L-phenylalanine p-nitrophenyl ester 
• 3397-32-8 N-(benzyloxycarbonyl)-phenylalanine-N-hydroxysuccinimide ester 
• 1161-13-3 N-Cbz-L-Phe 

Downstream Products

• 94343-39-2 (S)-2-amino-N-((S)-1-hydroxy-3-phenylpropan-2-yl)-3-phenylpropanamide 
• 52961-49-6 [(S)-1-((S)-1-Formyl-2-phenyl-ethylcarbamoyl)-2-phenyl-ethyl]-carbamic acid benzyl ester 
• 59490-18-5 Acetic acid (S)-2-((S)-2-benzyloxycarbonylamino-3-phenyl-propionylamino)-3-phenyl-propyl ester 
• 1523535-67-2 (S)-2-(((S)-2-(methylamino)-3-phenylpropyl)amino)-3-phenylpropan-1-ol 
• 1523535-29-6 (S)-5-benzyl-3-((S)-1-hydroxy-3-phenylpropan-2-yl)-1-methyl-4,5-dihydro-1H-imidazol-3-ium chloride 
• 80780-41-2 aurantiamide acetate 
• 58115-31-4 N-(N-benzoyl-L-phenylalanyl)-L-phenylalaninol 
• 2566-22-5 DL-N-benzoylphenylalanine 

Relevant academic research and scientific papers

Synthesis and biological evaluation of N-(carbobenzyloxy)-L-phenylalanine and N-(carbobenzyloxy)-L-aspartic acid-β-benzyl ester derivatives as potent topoisomerase IIα inhibitors

A new series of thirteen N-(carbobenzyloxy)-L-phenylalanine and N-(carbobenzyloxy)-L-aspartic acid-β-benzyl ester compounds were synthesized and evaluated for antiproliferative activity against four different human cancer cell lines: cervical cancer (HeLa

Highly Enantioselective Construction of Fluoroalkylated Quaternary Stereocenters via Organocatalytic Dehydrated Mannich Reaction of Unprotected Hemiaminals with Ketones

A general organocatalytic asymmetric dehydrated Mannich reaction of fluoroalkyl hemiaminals with ketones is reported. In this Mannich reaction, previously less explored aryl ketones showed great reactivity. By virtue of this efficient method, a wide range of biologically active β-amino ketones were directly obtained. More importantly, two different intermediates involved in the reaction were detected and identified by 19F NMR and HRMS analysis. Furthermore, the synthetic utility of the products was demonstrated by the synthesis of the biologically active fluoroalkyl β-amino alcohols.

Synthesis of novel chiral bidentate hydroxyalkyl-N-heterocyclic carbene ligands and their application in palladium-catalyzed Mizoroki-Heck couplings and asymmetric addition of diethylzinc to benzaldehyde

A small library of new chiral bidentate hydroxyalkyl-imidazolium salts 1 is conveniently synthesized on multi-gram scale from inexpensive and commercially available chiral pool amino acids. The corresponding carbenes, generated by deprotonation of imidazolium salts 1, in combination with palladium(II) chloride were tested in the Mizoroki-Heck coupling reaction. The most significant results in terms of yields and reactivities were achieved with low catalyst loading. The catalytic activities of these imidazolium salts were also investigated in the asymmetric addition of diethylzinc to benzaldehyde. The use of MgO nanoparticles as an additive in conjunction with these ligands played a crucial role in increasing the efficiency of these reactions.

Synthesis of novel chiral diamino alcohols and their application in copper-catalyzed asymmetric allylic oxidation of cycloolefins

The small library of new enantiomerically pure (S,S)-diamino alcohols 1 and their hydroxyldiamide precursors 2 were conveniently synthesized on a gram scale from inexpensive and commercially chiral pool amino acids. The catalytic and induced asymmetric ef

Design and synthesis of new N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides as anti-inflammatory agents

Twenty-four new dipeptide analogs (1-24) of aurantiamide acetate were designed, synthesized, and assayed for effects on superoxide anion generation and elastase release by human neutrophils in response to fMLP/CB. Among them, seven N-(fluorenyl-9-methoxycarbonyl) (Fmoc)-dipeptides (6, 9, 12, 14, 17, 18 and 20) showed potent inhibitory effects. Compounds 9 and 18 showed the most selective effects against human neutrophil elastase release, with IC50 values of 0.8 ± 0.1 and 1.7 ± 0.6 μM, respectively, and were 130-fold more potent than phenylmethylsulfonyl fluoride (PMSF), the positive control, in this anti-inflammatory assay. These two compounds could be developed as new lead anti-inflammatory agents.

Development of α-keto-based inhibitors of cruzain, a cysteine protease implicated in Chagas disease

Trypanosoma cruzi, a protozoan parasite, is the causative agent of Chagas disease, a major cause of cardiovascular disease in many Latin American countries. There is an urgent need to develop an improved therapy due to the toxicity of existing drugs and emerging drug resistance. Cruzain, the primary cysteine protease of T. cruzi, is essential for the survival of the parasite in host cells and therefore is an important target for the development of inhibitors as potential therapeutics. A novel series of α-ketoamide-, α-ketoacid-, α-ketoester-, and aldehyde-based inhibitors of cruzain has been developed. The inhibitors were identified by screening protease targeted small molecule libraries and systematically optimizing the P1, P2, P3, and P1′ residues using specific structure-guided methods. A total of 20 compounds displayed picomolar potency in in vitro assays and three inhibitors representing different α-keto-based inhibitor scaffolds demonstrated anti-trypanosomal activity in cell culture. A 2.3 A crystallographic structure of cruzain bound with one of the α-ketoester analogs is also reported. The structure and kinetic assay data illustrate the covalent binding, reversible inhibition mechanism of the inhibitor. Information on the compounds reported here will be useful in the development of new lead compounds as potential therapeutic agents for the treatment of Chagas disease and as biological probes to study the role that cruzain plays in the pathology. This study also demonstrates the validity of structure-guided approaches to focused library design and lead compound optimization.

Components of the Chinese drug 'Ti-ku-'pi'. Isolation and establishment of structure of a new dipeptide, lyciumamide

A new dipeptide, lyciumamide (1), was isolated from the Chinese crude drug 'Ti-ku-'pi', root bark of Lycium chinense MILL. (Solanaceae), and was shown by spectroscopy, chemical degradation, and synthesis to be N-benzoyl-L-phenylalanyl-L-phenylalaninol O-acetate (1).