80394-38-3

Upstream product

• 1738-64-3 2-benzoylamino-3-methyl-crotonic acid 
• 28897-81-6 2-phenyl-4-iso-propyl-4H-oxazolin-5-one 
• 107-18-6 allyl alcohol 
• 17498-50-9 (R)-valine hydrochloride 
• 98-88-4 benzoyl chloride 
• 2901-80-6 N-benzoyl-D,L-valine 
• 67-56-1 methanol 
• 640-68-6 D-Val-OH 
• 23405-15-4 benzoic acid N-hydroxysuccinimide ester 
• 72-18-4 L-valine 
• 65-85-0 benzoic acid 
• 132353-23-2 2-(benzyloxy)-4,6-dimethoxy-1,3,5-triazin 
• 1523-15-5 2,4-dinitrophenyl benzoate 
• 1694-28-6 2,5-dinitrophenyl benzoate 

Downstream Products

• 70019-93-1 methyl N-(N-benzoyl-L-valyl)glycinate 
• 75118-37-5 N-benzoyl-L-valyl-L-leucine ethyl ester 
• 4252-31-7 N-formylbenzamide 
• 1375475-51-6 (R)-N-(4-methylpent-1-en-3-yl)benzamide 
• 1221966-75-1 (S)-N-(1-(methoxy(methyl)amino)-3-methyl-1-oxobutan-2-yl)benzamide 
• 81019-02-5 N-[(S)-2-Methyl-1-((S)-1-phenyl-ethylcarbamoyl)-propyl]-benzamide 
• 109256-82-8 N-benzoyl-D-valyl chloride 
• 1492-13-3 (2R)-2-(benzoylamino)-3-methylbutyric acid methyl ester 
• 160024-72-6 (3S)-3-(N-Benzoylamino)-4-methyl-2-pentanone 
• 144317-06-6 Bz-Val-Ser-OMe 
• 28897-81-6 (S)-4-isopropyl-2-phenyl-4H-oxazol-5-one 
• 5839-93-0 (R)-4-Isopropyl-2-phenyl-4H-oxazol-5-one 
• 42807-42-1 N-benzyl-L-valinol 
• 28897-81-6 2-phenyl-4-iso-propyl-4H-oxazolin-5-one 

Relevant academic research and scientific papers

4-Sulfamoylphenylalkylamides as Inhibitors of Carbonic Anhydrases Expressed in Vibrio cholerae

A current issue of antimicrobial therapy is the resistance to treatment with worldwide consequences. Thus, the identification of innovative targets is an intriguing challenge in the drug and development process aimed at newer antimicrobial agents. The state-of-art of anticholera therapy might comprise the reduction of the expression of cholera toxin, which could be reached through the inhibition of carbonic anhydrases expressed in Vibrio cholerae (VchCAα, VchCAβ, and VchCAγ). Therefore, we focused our interest on the exploitation of sulfonamides as VchCA inhibitors. We planned to design and synthesize new benzenesulfonamides based on our knowledge of the VchCA catalytic site. The synthesized compounds were tested thus collecting useful SAR information. From our investigation, we identified new potent VchCA inhibitors, some of them displayed high affinity toward VchCAγ class, for which few inhibitors are currently reported in literature. The best interesting VchCAγ inhibitor (S)-N-(1-oxo-1-((4-sulfamoylbenzyl)amino)propan-2-yl)furan-2-carboxamide (40) resulted more active and selective inhibitor when compared with acetazolamide (AAZ) as well as previously reported VchCA inhibitors.

GRANZYME B DIRECTED IMAGING AND THERAPY

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

Palladium-catalyzed asymmetric decarboxylative allylation of azlactone enol carbonates: Fast access to enantioenriched α-allyl quaternary amino acids

We report a fast protocol for the synthesis of enantioenriched quaternary 4-allyl oxazol-5-ones. The key step is a Pd-catalyzed enantioselective Tsuji allylation of azlactone allyl enol carbonates, which can be easily prepared starting from racemic α-amino acids. The use of (R,R)-DACH-phenyl Trost chiral ligand allowed the attainment of the allylated derivatives in very good yields (83–98 %) and with ee up to 85 %. Scaling up the allylation protocol to gram quantities did not affect the yields end ee values. The produced 4-allyl azlactones can be converted into the corresponding quaternary amino acids or submitted to further synthetic elaborations exploiting the allyl moiety as a handle for the attachment of alkyl and aryl groups. After hydrolysis of the azlactone ring, the zwitterionic amino acids can be attained in enantiopure or nearly optically pure form through only one recrystallization step.

Latent Bronsted Base Solvent-Assisted Amide Formation from Amines and Acid Chlorides

Weakly basic amines, including even neutral amines such as nitroaniline and aminocarboxylic acids, react with acid chlorides very efficiently in N, N -dimethylacetamide (DMAC), without addition of a base, to give the corresponding amides in high yields. The role of DMAC and related solvents as latent Bronsted bases was studied in these amidation reactions. Less basic amines, such as aromatic amines, reacted with benzoyl chloride faster than more basic aliphatic amines.

Dynamic Kinetic Resolution of N-Protected Amino Acid Esters via Phase-Transfer Catalytic Base Hydrolysis

Asymmetric base hydrolysis of α-chiral esters with synthetic small-molecule catalysts is described. Quaternary ammonium salts derived from quinine were used as chiral phase-transfer catalysts to promote the base hydrolysis of N-protected amino acid hexafluoroisopropyl esters in a CHCl3/NaOH (aq) via dynamic kinetic resolution, providing the corresponding products in moderate to good yields (up to 99%) with up to 96:4 er. Experimental and computational mechanistic studies using DFT calculation and pseudotransition state (pseudo-TS) conformational search afforded a TS model accounting for the origin of the stereoselectivity. The model suggested π-stacking and H-bonding interactions play essential roles in stabilizing the TS structures.

Development of a method for the synthesis of 2,4,5-trisubstituted oxazoles composed of carboxylic acid, amino acid, and boronic acid

A novel method for the synthesis of trisubstituted oxazoles via a one-pot oxazole synthesis/Suzuki–Miyaura coupling sequence has been developed. One-pot formation of 5-(triazinyloxy)oxazoles using carboxylic acids, amino acids and a dehydrative condensing reagent, DMT-MM, followed by Ni-catalyzed Suzuki–Miyaura coupling with boronic acids provided the corresponding 2,4,5-trisubstituted oxazoles in good yields.

Isotope-labeled differential profiling of metabolites using N-benzoyloxysuccinimide derivatization coupled to liquid chromatography/high-resolution tandem mass spectrometry

Rationale An isotopic labeling strategy based on derivatizing amine-containing metabolites has been developed using light (12C6) and heavy (13C6) N-benzoyloxysuccinimide reagents for semi-targeted metabolomic applications. Methods Differentially labeled samples were combined and analyzed simultaneously by liquid chromatography/high-resolution tandem mass spectrometry (LC/HR-MS/MS) to compare relative amounts of amine-containing metabolites. The selectivity of the reaction was determined with model metabolites and was shown to also be applicable to thiol and phenol moieties. The potential for relative quantitation was evaluated in cell extracts and the method was then applied to quantify metabolic perturbations occurring in human cultured cells under normal vs. oxidative stress conditions. Results A total of 279 derivatized features were detected in HL60 cell extracts, 77 of which yielded significant concentration changes upon oxidative stress treatment. Based on accurate mass measurements and MS/MS spectral matching with reference standard solutions, 10 metabolites were clearly identified. Derivatized compounds were found to have diagnostic fragment ions from the reagent itself, as well as structurally informative ions useful for metabolite identification. Conclusions This simple derivatization reaction can be applied to the relative quantitation of amine-, thiol- and phenol-containing compounds, with improved sensitivity and chromatographic peak shapes due to the increased hydrophobicity of polar metabolites not readily amenable to reversed-phase LC/MS analysis.

Some hydrazones of 2-aroylamino-3-methylbutanohydrazide: Synthesis, molecular modeling studies, and identification as stereoselective inhibitors of HIV-1

In accordance with our antiviral drug development attempt, acylhydrazone derivatives bearing amino acid side chains were synthesized for the evaluation of their antiviral activity against various types of viruses. Among these compounds, 8S, 11S, and 12S showed anti-HIV-1 activity with a 50% inhibitory concentration (IC50) = 123.8 μM (selectivity index, SI > 3), IC50 = 12.1 μM (SI > 29), IC50 = 17.4 μM (SI > 19), respectively. Enantiomers 8 R, 11R, and 12R were inactive against the HIV-1 strain IIIB. Hydrazones 8S, 11S, and 12 S which were active against HIV-1 wild type showed no inhibition against a double mutant NNRTI-resistant strain (K103N;Y181C). Molecular docking calculations of R- and S-enantiomers of 8, 11, and 12 were performed using the hydrazone-bound novel site of HIV-1 RT. Copyright

Iodine(III)-promoted synthesis of oxazolines from N-allylamides

PhI(OAc)2 (activated by BF3·OEt2) has been used to promote the oxidative cyclization of N-allylamides to give oxazolines. The reaction products are formed in high yield and, when a branched allylic amine is used, high diastereoselectivity. Initial mechanistic experiments suggest that the final C-O bond is formed from a reactive tight ion pair, rather than a neutral external nucleophile.

Synthesis, characterization, and cytotoxicity of complexes of platinum(u) with 2,2'-bipyridine and N-benzoyl-L-amino acid dianion

Four new platinum(II) complexes (1-4) with N-benzoyl-L-amino acid and bipy were synthesized and characterized by elemental analysis, IR, UV, 1H NMR, and mass spectra. The crystal structure of 1 was determined by X-ray diffraction analysis. Cytotoxicities were measured by MTT and SRB assays. Complexes 1-4 exert cytotoxicity with selectivity against HL-60, Bel-7402, BGC-823, and KB cell lines. This suggests that amino acids and acylated groups have important effects on cytotoxicity; the cytotoxicity is also related to the species of tumor cells, but the IC50 values do not show definite correlation with the variation of amino acids and acylated groups.