145902-48-3

Upstream product

• 1539-57-7 diethyl 2,6-dimethyl-4-benzyl-1,4-dihydropyridine-3,5-dicarboxylate 
• 34101-07-0 (2S)-2-[N-(tert-butoxycarbonyl)amino]-1-imidazol-1-yl-3-phenylpropan-1-one 
• 87694-53-9 Boc-Phe-OH N,O-dimethyl hydroxamate 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 173018-44-5 (1-benzyl-2-hydroxy-3-phenyl-propyl)-carbamic acid tert-butyl ester 
• 145902-49-4 (2R,3S)-1,4-diphenyl-2-hydroxy-3-amino-N-Boc-butane 

Relevant academic research and scientific papers

Combined Photoredox and Carbene Catalysis for the Synthesis of Ketones from Carboxylic Acids

As a key element in the construction of complex organic scaffolds, the formation of C?C bonds remains a challenge in the field of synthetic organic chemistry. Recent advancements in single-electron chemistry have enabled new methods for the formation of various C?C bonds. Disclosed herein is the development of a novel single-electron reduction of acyl azoliums for the formation of ketones from carboxylic acids. Facile construction of the acyl azolium in situ followed by a radical–radical coupling was made possible merging N-heterocyclic carbene (NHC) and photoredox catalysis. The utility of this protocol in synthesis was showcased in the late-stage functionalization of a variety of pharmaceutical compounds. Preliminary investigations using chiral NHCs demonstrate that enantioselectivity can be achieved, showcasing the advantages of this protocol over alternative methodologies.

Regio- and Stereoselective Modification of Chiral α-Amino Ketones by Pd-Catalyzed Allylic Alkylation

Chiral α-amino ketones are excellent nucleophiles for stereoselective palladium-catalyzed allylic alkylations. Both chiral as well as achiral allylic substrates can be applied, while the stereochemical outcome of the reaction is controlled by the chiral ketone enolate. The substituted amino ketones formed can be reduced stereoselectively, and up to five consecutive stereogenic centers can be obtained. This approach can be used for the synthesis of highly substituted piperidine derivatives.

Rapid discovery and structure-activity profiling of novel inhibitors of human immunodeficiency virus type 1 protease enabled by the copper(I)-catalyzed synthesis of 1,2,3-triazoles and their further functionalization

Building from the results of a computational screen of a range of triazole-containing compounds for binding efficiency to human immunodeficiency virus type 1 protease (HIV-1-Pr), a novel series of potent inhibitors has been developed. The copper(I)-cataly

HIV protease inhibitors

Combinatorial libraries of HIV and FIV protease inhibitors are characterized by alpha-keto amide or hydroxyethylamine core structures flanked by on one side by substituted pyrrolidines, piperidines, or azasugars and on the other side by phenylalanine, tyrosine, or substituted tyrosines. The libraries are synthesized via a one step coupling reaction. Highly efficacious drug candidates are identified by screening the libraries for binding and inhibitory activity against both HIV and FIV protease. Drug candidates displaying clinically useful activity against both HIV and FIV protease are identified as being potentially resistive against a loss of inhibitory activity due to development of resistant strains of HIV.

TIGHT-BINDING INHIBITORS OF LEUKOTRIENE A4 HYDROLASE

Inhibitors of leukotriene A 4 hydrolase are disclosed, corresponding to Formula I, below: STR1 wherein the depicted--NH 2 group is in the (S) configuration;--W is--CH 2 SH,--CH 2 NH. sub.2 or C(=Z)--Y, wherein =Z is =O, or--H and--OH; and--Y is selected from the group consisting of (a) phenyl, (b) trifluoromethylphenyl, (c) carboxyphenyl, (d) benzyl, (e) C 1-C 6 alkylenecarboxyl, (f) C. sub.1-C 6 alkyl, (g) C 2-C 6 alkenyl, (h) C 1-C 6 alkylenephenyl and (i)--C(=O)--X--R. sup.1 wherein X is O or NH and, R 1 is selected from the group consisting of C 1-C 6 alkyl, C 1-C 6 alkylenecarboxyl, and benzyl; R 2 is hydrogen, benzyloxy or 2-naphthylmethyloxy, and a pharmaceutically acceptable acid addition salt thereof. Inhibitors wherein--W is--CH 2 SH,--CH 2 NH 2 or C(=Z)--Y wherein =Z is =O and--Y is--C(=O)--X--R. sup.1 are particularly preferred, as are those compounds wherein =Z is = O and--Y is selected from the group consisting of (a) phenyl, (b) trifluoromethylphenyl, (c) carboxyphenyl, (d) benzyl, (e) C 1-C 6 alkylenecarboxyl, (f) C 1-C 6 alkyl, (g) C 2-C 6 alkenyl, (h) C 1-C 6 alkylenephenyl. An inhibitor where--W is--CH 2 SH,--CH 2 NH 2 or C(=Z)--Y wherein =Z is =O and--Y is--C(=O)--X--R 1 is particularly preferred, as are those inhibitor compounds where =Z is =O and--Y is (a)--(h) .

Development of selective tight-binding inhibitors of leukotriene A4 hydrolase

Leukotriene A4 hydrolase is a zinc-containing enzyme which exhibits both epoxide hydrolase and aminopeptidase activities. Since the enzyme product leukotriene B4 is an inflammatory mediator, it is of interest to develop selective inh