2441-07-8

Upstream product

• 17407-56-6 (R)-2-Hydroxy-3-methylbutyric acid 
• 100-51-6 benzyl alcohol 
• 4026-18-0 2-hydroxy-3-methylbutanoic acid 
• 37526-89-9 benzyl 3-methylbut-2-enoate 
• 76585-78-9 phenylmethyl 3-methyl-2-oxobutanoate 
• 1760-46-9 diphenylacetic anhydride 
• 117-34-0 2,2-diphenylacetic acid 
• 640-68-6 D-Val-OH 
• 100-39-0 benzyl bromide 
• 908094-04-2 phenyldiazomethane 

Downstream Products

• 126686-50-8 TFA_.Val-D-Hyv-OBzl 
• 126686-49-5 L-D-3-Methyl-2-(2-amino-3-methyl-butyryloxy)-buttersaeure-benzylester 
• 32770-05-1 Boc-D-Val-Lac-Val-D-Hyv-OBzl 
• 32770-12-0 Boc-(D-Val-Lac-Val-D-Hyv)2-OBzl 
• 1374586-87-4 C₃₄H₅₄N₂O₉ 
• 872689-54-8 (S)-N-butoxycarbonyl-N-methylvaline (1R)-2-methyl-1-[(phenylmethoxy)carbonyl]propyl ester 
• 2441-17-0 O-(2-Methoxycarbonyl-benzoyl)-(α-hydroxy-isovaleriansaeure-benzylester) 
• 2634-18-6 O-(2-Methoxycarbonyl-benzoyl)-α-hydroxy-isovaleryl-alanin-benzylester 
• 2528-08-7 O-(2-Methoxycarbonyl-benzoyl)-α-hydroxy-isovaleryl-valin-benzylester 
• 2441-12-5 O-(2-Methoxycarbonyl-benzoyl)-α-hydroxy-isovaleriansaeure 
• 2528-12-3 O-(2-Methoxycarbonyl-benzoyl)-DL-(α-hydroxy-isovaleryl)-DL-alanin 
• 2634-21-1 O-(2-Methoxycarbonyl-benzoyl)-DL-(α-hydroxy-isovaleryl)-DL-valin 
• 1041400-00-3 1-(benzyloxy)-3-methyl-1-oxobutan-2-yl pyrrolidine-1-carboxylate 
• 1208982-39-1 benzyl (R)-2-(diphenylacetyloxy)-3-methylbutanoate 

Relevant academic research and scientific papers

Synthetic Indolactam V Analogues as Inhibitors of PAR2-Induced Calcium Mobilization in Triple-Negative Breast Cancer Cells

Human proteinase-activated receptor 2 (PAR2), a transmembrane G-protein-coupled receptor (GPCR), is an attractive target for a novel anticancer therapy, as it plays a critical role in cell migration and invasion. Selective PAR2 inhibitors therefore have potential as anti-metastatic drugs. Knowing that the natural product teleocidin A2 is able to inhibit PAR2 in tumor cells, the goal of the present study was to elaborate structure–activity relationships and to identify potent PAR2 inhibitors with lower activity against the adverse target, protein kinase C (PKC). For this purpose, an efficient gram-scale total synthesis of indolactam V (i.e., the parent structure of all teleocidins) was developed, and a library of derivatives was prepared. Some compounds were indeed found to exhibit high potency as PAR2 inhibitors at low nanomolar concentrations with improved selectivity (relative to teleocidin A2). The pseudopeptidic fragment bridging the C3 and C4 positions of the indole core proved to be essential for target binding, whereas activity and target selectivity depends on the substituents at N1 or C7. This study revealed novel derivatives that show high efficacy in PAR2 antagonism combined with increased selectivity.

Synthesis of Natural and Unnatural Cyclooligomeric Depsipeptides Enabled by Flow Chemistry

Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b). A reliable flow chemistry protocol was established for the coupling and macrocyclisation to form challenging N-methylated amides. This flexible approach has allowed the rapid synthesis of both natural and unnatural depsipeptides in high yields, enabling further exploration of their promising biological activity. Harnessing technology: Flow chemistry has been successfully integrated into the synthesis of a series of cyclooligomeric depsipeptides of three different ring sizes including the natural products beauvericin (1 a), bassianolide (2 b) and enniatin C (1 b), resulting in increased overall yields, while decreasing the effort required for the researcher.

COMBINATIONS OF HEPATITIS C VIRUS INHIBITORS

The present disclosure is generally directed to antiviral compounds, and more specifically directed to combinations of compounds which can inhibit the function of the NS5A protein encoded by Hepatitis C virus (HCV), compositions comprising such combinations, and methods for inhibiting the function of the NS5A protein.

NOVEL PYRAZOLO PYRIMIDINE DERIVATIVES AND THEIR USE AS MALT1 INHIBITORS

The present invention describes new pyrazolo-pyrimidine derivatives of formula (I) or a pharmaceutically acceptable salt thereof; (I) wherein, R1 is halogen, cyano, or C1-C3alkyl optionally substituted by halogen; R2 is C1-C6alkyl optionally substituted one or more times by C1-C6alkyl, C2-C6alkenyl, hydroxyl, N,N-di-C1-C6alkyl amino, N-mono-C1-C6alkyl amino, O-Rg, Rg, phenyl, or by C1-C6alkoxy wherein said alkoxy again may optionally be substituted by C1-C6alkoxy, N,N-di-C1-C6alkyl amino, Rg or phenyl; C3-C6cycloalkyl optionally substituted by C1-C6alkyl, N,N-di-C1-C6alkyl amino or C1-C6alkoxy-C1-C6alkyl, and/or two of said optional substituents together with the atoms to which they are bound may form an annulated or spirocyclic 4 - 6 membered saturated heterocyclic ring comprising 1 - 2 O atoms; phenyl optionally substituted by C1-C6alkoxy; a 5 - 6 membered heteroaryl ring having 1 to 3 heteroatoms selected from N and O said ring being optionally substituted by C1-C6alkyl which may be optionally substituted by amino or hydroxy; Rg; or N,N-di-C1-C6alkyl amino carbonyl; and R is phenyl independently substituted two or more times by Ra, 2-pyridyl independently substituted one or more times by Rb, 3-pyridyl independently substituted one or more times by Rc, or 4-pyridyl independently substituted one or more times by Rd; which are generally interacting with MALT1 proteolytic and/or autoproteolytic activity, and in particular which may inhibit said activity. The present invention further describes the synthesis of said new pyrazolo-pyrimidine derivatives, their use as a medicament, especially by interacting with MALT1 proteolytic and/or autoproteolytic activity.

Surface-based ammonium ion sensor and methods of making thereof

A compound sensitive to and selective for ammonium ions over other ions. A sensor fabricated from a self assembled monolayer of said compound on gold, exhibiting sensitivity and selectivity for ammonium ions over other ions in aqueous solutions, including blood. A method of preparation of said compound and said sensor.

Synthesis, characterization and activity of new phosphonate dipeptides as potential inhibitors of VanX

VanX, a Zn(II)-dependent D-ala-D-ala dipeptidase, is essential for vancomycin resistance in Enterococcus faecium. The enzymatic activity of VanX was previously found to be inhibited competitively by 2-{[(1-aminoethyl) (hydroxy) phosphoryl]oxy} propanoic acid (1B). Here we report the synthesis and characterization of seven phosphonate dipeptide analogs of D-ala-D-ala with various substituent, the activity evaluation indicated that six of these phosphonate analogs inhibit VanX with IC50 of 0.48-8.21 mM. These data revealed a structure-activity relationship which is that the large substituent group on β-carbon resulted in low binding affinity of the phonphonate analog to VanX. This information will be helpful to guide the design and synthesis of the tightly-binding inhibitors for VanX.

A total synthesis of the ammonium ionophore, (-)-enniatin B

A nine-step (longest linear) batch total synthesis of the cyclic hexadepsipeptide (-)-enniatin B is described. The synthesis minimizes precipitation during reaction conditions for adaptability to flow synthesis. The route was used to prepare >100 mg of th

METHOD FOR PRODUCING OPTICALLY ACTIVE 2-HYDROXY ESTER AND NOVEL INTERMEDIATE COMPOUND

Disclosed is a method for producing an optically active 2-hydroxy ester, comprising selectively esterifying one enantiomer of a racemic 2-hydroxy ester in a solvent containing a catalyst such as tetramisole or benzotetramisole, and a carboxylic acid anhydride, or a carboxylic acid anhydride and a carboxylic acid. In particular, in the case where the solvent contains a carboxylic acid anhydride, but does not contain a carboxylic acid, as the carboxylic acid anhydride, a carboxylic acid anhydride containing a tertiary or quaternary carbon atom in the a-position is used. On the other hand, in the case where the solvent contains a carboxylic acid anhydride and a carboxylic acid, as the carboxylic acid, a carboxylic acid containing a tertiary or quaternary carbon atom in the a-position is used.

A convenient method for the kinetic resolution of racemic 2-hydroxyalkanoates using diphenylacetic anhydride (DPHAA) and a chiral acyl-transfer catalyst

Diphenylacetic anhydride (DPHAA) was found to be a useful reagent for the kinetic resolution of racemic 2-hydroxyalkanoates in the presence of a catalytic amount of (R)-benzotetramisole ((R)-BTM). The combined use of DPHAA and (R)-BTM effectively produced a variety of the optically active 2-hydroxyalkanoates and the corresponding 2-acyloxyalkanoates from racemic 2-hydroxyalkanoates (s-values = 42-177). A fairly broad substrate scope was demonstrated by this novel chiral induction system. We also revealed that the use of only 0.3 equiv of DPHAA is enough to provide the optically active 2-acyloxyalkanoates in good yields and with excellent ee's by the added use of 0.3 equiv of pivalic anhydride for the kinetic resolution of the racemic 2-hydroxyalkanoates. Copyright

Membrane-based sensing approaches

Tethered bilayer lipid membranes can be used as model platforms to host membrane proteins or membrane-active peptides, which can act as transducers in sensing applications. Here we present the synthesis and characterization of a valinomycin derivative, a depsipeptide that has been functionalized to serve as a redox probe in a lipid bilayer. In addition, we discuss the influence of the molecular structure of the lipid bilayer on its ability to host proteins. By using electrical impedance techniques as well as neutron scattering experiments, a clear correlation between the packing density of the lipids forming the membrane and its ability to host membrane proteins could be shown. CSIRO 2011.