63398-31-2

Upstream product

• 875-74-1 (R)-phenylglycine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 33125-05-2 Boc-D-Phg-OH 
• 543-27-1 isobutyl chloroformate 
• 2935-35-5 (S)-2-phenylglycine 
• 2900-27-8 (2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid 

Downstream Products

• 620594-45-8 tert-butyl N-((1S)-2-{[(1S)-1-(hydroxymethyl)-2-methylpropyl]amino}-2-oxo-1-phenylethyl)carbamate 
• 115549-25-2 (S)-3-(tert-Butoxycarbonylamino)-1-diazo-3-phenylpropan-2-one 
• 1207620-22-1 C₂₂H₂₈N₂O₃ 
• 1350745-03-7 C₃₀H₄₀N₂O₈ 
• 1408318-93-3 1-benzyl-3(S)-phenyl-1,4-diazepine-2,5-dione 
• 1408318-78-4 C₁₈H₂₀N₂O₃ 
• 58619-70-8 (6R)-7t-((R)-2-amino-2-phenyl-acetylamino)-3-fluoromethyl-8-oxo-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 
• 1408318-94-4 1-benzyl-3(R)-phenyl-1,4-diazepine-2,5-dione 
• 1408318-80-8 C₁₈H₂₀N₂O₃ 
• 34632-03-6 tert-butyl (6R,7R)-7-(2-((tert-butoxycarbonyl)amino)-2-phenylacetamido)-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo-[4.2.0]oct-2-ene-2-carboxylate 
• 926293-43-8 (R)-t-butyl (2-(t-butylamino)-2-oxo-1-phenylethyl)carbamate 

Relevant academic research and scientific papers

A Synthetic Dual Drug Sideromycin Induces Gram-Negative Bacteria to Commit Suicide with a Gram-Positive Antibiotic

Many antibiotics lack activity against Gram-negative bacteria because they cannot permeate the outer membrane or suffer from efflux and, in the case of β-lactams, are degraded by β-lactamases. Herein, we describe the synthesis and studies of a dual drug conjugate (1) of a siderophore linked to a cephalosporin with an attached oxazolidinone. The cephalosporin component of 1 is rapidly hydrolyzed by purified ADC-1 β-lactamase to release the oxazolidinone. Conjugate 1 is active against clinical isolates of Acinetobacter baumannii as well as strains producing large amounts of ADC-1 β-lactamase. Overall, the results are consistent with siderophore-mediated active uptake, inherent activity of the delivered dual drug, and in the presence of β-lactamases, intracellular release of the oxazolidinone upon cleavage of the cephalosporin to allow the freed oxazolidinone to inactivate its target. The ultimate result demonstrates that Gram-positive oxazolidinone antibiotics can be made to be effective against Gram-negative bacteria by β-lactamase triggered release.

Solution-phase synthesis of novel seven-membered cyclic dipeptides containing α- And β-amino acids

A convenient synthetic procedure for the preparation of seven-membered cyclic α,β-dipeptides is described. Following coupling of N-protected α-amino acids with N-substituted β-amino acid tert-butyl esters, that affords linear α,β-dipeptides, the protecting groups at the terminal functionalities were removed and the open-chain dipeptides were cyclized with phenylphosphonic dichloride, PhP(O)Cl2, to give the desired cyclic α,β-dipeptides in good yields. NMR studies, X-ray diffraction analysis, and DFT calculations provided evidence for the conformation adopted by these cyclic dipeptides in solution, in the solid-state, and in the gas phase.

Carbohydrate-based pseudo-dipeptides: New ligands for the highly enantioselective Ru-catalyzed transfer hydrogenation reaction

Ruthenium-complexes of novel carbohydrate based pseudo-dipeptide ligands effectively and selectively catalyze the reduction of a broad range of aryl-alkyl ketones under ATH conditions. Excellent enantioselectivities (>99% ee) are obtained using aminosugars as the sole source of chirality. The Royal Society of Chemistry 2011.

Design of chiral hydroxyalkyl- and hydroxyarylazolinium salts as new chelating diaminocarbene ligand precursors devoted to asymmetric copper-catalyzed conjugate addition

The design and the synthesis of a set of new chiral hy- droxyalkyl- and hydroxyaryl-chelating diaminocarbene ligands is reported. Comparative catalytic studies show the importance of the scaffold design around the NHC unit to obtain a high enantiocontrol in Cu-catalyzed asymmetric conjugate addition (ACA). Whereas low selectivities are observed when the stereogenic centre is placed within the N-heterocyclic ring, an interesting match effect can be observed when central chirality is located within both of the two side chains, which enables up to 92 % ee in the catalysis reaction. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009.

CHEMOKINE RECEPTOR BINDING COMPOUNDS

The present invention relates to chemokine receptor binding compounds, pharmaceutical compositions and their use. More specifically, the present invention relates to modulators of chemokine receptor activity, preferably modulators of CCR4 or CCR5. In one aspect, these compounds demonstrate protective effects against infection of target cells by a human immunodeficiency virus (HIV).

An efficient synthesis of cyclic urethanes from Boc-protected amino acids through a metal triflate-catalyzed intramolecular diazocarbonyl insertion reaction

A simple and efficient synthesis of cyclic urethanes and related oxazinanones 1a-l from diazoketones 3a-l is described. The transformation involves generation of carbenes by activation of diazo groups using metal triflates in intramolecular diazocarbonyl insertion reactions in high overall yields.

Asymmetric cyanosilylation of aldehydes catalyzed by novel chiral tetraaza-titanium complexes

The asymmetric addition of trimethylsilyl cyanide (TMSCN) to a range of aldehydes was efficiently catalyzed by a novel, easily prepared C 2-symmetric chiral tetraaza-Ti(IV) complex in high yields with up to 92% ee under mild conditions. A negative nonlinear effect between the ee of the ligand and the ee of the product was observed. Georg Thieme Verlag Stuttgart.

Highly Enantioselective Ruthenium-Catalyzed Reduction of Ketones Employing Readily Available Peptide Ligands

Highly efficient and selective catalysts for the asymmetric reduction of aryl alkyl ketones under hydrogen-transfer conditions (2-propanol) were obtained by combining a novel class of pseudo-dipeptide ligands with [{RuCl 2(p-cymene)}2]. A library of 36 dipeptide-like ligands was prepared from N-Boc-protected α-amino acids and the enantiomers of 2-amino-1-phenylethanol and 1-amino-2-propanol. The catalyst library was evaluated with the reduction of acetophenone and excellent enantioselectivity of 1-phenylethanol was obtained with several of the novel catalysts. A ligand based on the combination of N-Boc-L-alanine and (S)-1-amino-2-propanol (ligand A-(S)-4) was found to be particular effective. When the situ formed ruthenium complex of this ligand was employed as the catalyst in the hydrogen-transfer reaction of various aryl alkyl ketones, the corresponding alcohol products were achieved in excellent enantioselectivity (up to 98% ee).

Employing the structural diversity of nature: Development of modular dipeptide-analogue ligands for ruthenium-catalyzed enantioselective transfer hydrogenation of ketones

A library of novel dipeptideanalogue ligands based on the combination of tert-butoxycarbonyl(N-Boc)-protected a-amino acids and chiral vicinal amino alcohols were prepared. These highly modular ligands were combined with [{RuCl2(p-cymene)}2 and the resulting metal complexes were screened as catalysts for the enantioselective reduction of acetophenone under transfer hydrogenation conditions using 2-propanol as the hydrogen donor. Excellent enantioselectivity of 1-phenylethanol (up to 98% ee) was achieved with several of the novel catalysts. Although most of the ligands contained two stereocenters, it was demonstrated that the absolute configuration of the product alcohol was determined by the configuration of the amino acid part of the ligand. Employing ligands based on L-amino acids generated S-configured products, and catalysts based on Damino acids favored the formation of the R-configured alcohol. The combination N-Boc-L-alanine and (R)-phenylglycinol (Boc-L-Ab) or its enantiomer (N-Boc-D-alanine and (S)-phenylglycinol, Boc-D-Aa) proved to be the best ligands for the reduction process. Transfer hydrogenation of a number of aryl alkyl ketones were evaluated and excellent enantioselectivity, up to 96 % ee, was obtained.

Design of plasma kallikrein inhibitors: Functional and structural requirements of plasma kallikrein inhibitors

The synthetic plasma kallikrein (PK) inhibitor trans-4- aminomethylcyclohexanecarbonylphenylalanine-4-carboxymethylanilide (PKSI- 527) consists of three parts. Each part was replaced by analogues in an attempt to improve the potency and the selectivity of PKSI-527. Among the peptides examined, trans-4-aminomethyl-cyclohexanecarbonylphenylalanine-4- carboxyanilide (peptide 16) inhibited PK with a high selectivity and an IC50 value of 2.7 μM, being as potent as PKSI-527.