190260-92-5

Usage

Uses

Used in Organic Synthesis:
N-Boc-D-valine N'-methoxy-N'-methylamide is used as a building block for the synthesis of various peptides and peptidomimetics due to its stability and compatibility with solid-phase peptide synthesis.
Used in Pharmaceutical Research:
N-Boc-D-valine N'-methoxy-N'-methylamide is used as a research compound for the development of new therapeutic agents for various diseases.
Used in Protease Inhibition:
N-Boc-D-valine N'-methoxy-N'-methylamide has been studied for its potential as a protease inhibitor, which could have applications in the treatment of diseases where protease activity is a factor.

Upstream product

• 13734-41-3 t-Boc-L-valine 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 22838-58-0 Boc-D-Val-OH 
• 16645-06-0 N,N-dimethylhydroxylamine hydrochloride 

Downstream Products

• 618430-36-7 (±)-tert-butyl (2-methyl-4-oxo-6-phenylhexan-3-yl)carbamate 
• 648858-71-3 (R)-4-N-(t-butoxycarbonyl)amino-5-methyl-1-phenyl-3-hexanone 
• 1044664-08-5 N-(3-aminopropyl)-N-{1-[7-chloro-4-oxo-3-(phenylmethyl)-4H-pyrano[2,3-b]pyridin-2-yl]-2-methylpropyl}-4-methylbenzamide 
• 1044664-07-4 7-chloro-2-[2-methyl-1-(7-oxohexahydro-1H-1,4-diazepin-1-yl)propyl]-3-(phenylmethyl)-4H-pyrano[2,3-b]pyridin-4-one 
• 618430-94-7 [(R)-(E)-1-isopropyl-4-(3-methoxy-phenyl)-2-oxo-butyl]-carbamic acid tert-butyl ester 
• 618430-92-5 [(R)-(E)-1-isopropyl-4-(3-methoxy-phenyl)-2-oxo-but-3-enyl]-carbamic acid tert-butyl ester 
• 106391-88-2 (2R)-2-[(tert-butoxycarbonyl)amino]-3-methylbutylaldehyde 

Relevant academic research and scientific papers

Binding cooperativity between a ligand carbonyl group and a hydrophobic side chain can be enhanced by additional H-bonds in a distance dependent manner: A case study with thrombin inhibitors

One of the underappreciated non-covalent binding factors, which can significantly affect ligand-protein binding affinity, is the cooperativity between ligand functional groups. Using four different series of thrombin inhibitors, we reveal a strong positiv

Cu(I)-catalyzed synthesis of dihydropyrimidin-4-ones toward the preparation of β- And β3-amino acid analogues

A copper(I)-catalyzed synthesis of substituted dihydropyrimidin-4-ones from propargyl amides via the formation of ketenimine intermediate has been successfully developed; the synthesis afforded good isolated yields (80-95%). The mild reaction conditions at room temperature allow the reaction to proceed to completion in a few hours without altering the stereochemistry. Further, by involving a variety of reactive nucleophiles, the obtained substituted dihydropyrimidin-4-ones were elegantly transformed into the corresponding β- and β3-amino acid analogues.

Synthesis of α, β-unsaturated γ-amino esters with unprecedented high (E)-stereoselectivity and their conformational analysis in peptides

Mild, efficient and racemization-free synthesis of N-protected α, β-unsaturated γ-amino esters with unprecedented high E- stereoselectivity is described. This method is found to be compatible with Boc-, Fmoc- and other side chain protecting groups. The crystal conformations of the vinylogous γ-amino esters in monomers and in homo- and mixed dipeptides are studied. Further, the vinylogous homo-dipeptide showed a β-sheet conformation, while mixed α- and α,β-unsaturated γ-hybrid dipeptide adapted an irregular structure in single crystals.

Preparation of α-hydroxy-β-Fmoc amino acids from N-Boc amino acids

A general method for the conversion of N-Boc amino acids into their homologated α-hydroxy-β-Fmoc amino acids is described. The protocol involved preparation of the amino aldehyde by reduction of the corresponding Weinreb amides, hydrocyanation, and hydrol

Defining the structural parameters that confer anticonvulsant activity by the site-by-site modification of (R)-N′-benzyl 2-amino-3-methylbutanamide

Primary amino acid derivatives (PAADs) (N′-benzyl 2-substituted 2-amino acetamides) are structurally related to functionalized amino acids (FAAs) (N′-benzyl 2-substituted 2-acetamido acetamides) but differ by the absence of the terminal N-acetyl group. Both classes exhibit potent anticonvulsant activities in the maximal electroshock seizure animal model, and the reported structure-activity relationships (SARs) of PAADs and FAAs differ in significant ways. Recently, we documented that PAAD efficacy was associated with a hydrocarbon moiety at the C(2)-carbon, while in the FAAs, a substituted heteroatom one atom removed from the C(2)-center was optimal. Previously in this issue, we showed that PAAD activity was dependent upon the electronic properties of the 4′-N′-benzylamide substituent, while FAA activity was insensitive to electronic changes at this site. In this study, we prepared analogues of (R)-N′-benzyl 2-amino-3-methylbutanamide to identify the structural components for maximal anticonvulsant activity. We demonstrated that the SAR of PAADs and FAAs diverged at the terminal amide site and that PAADs had considerably more structural latitude in the types of units that could be incorporated at this position, suggesting that these compounds function according to different mechanism(s).

Synthesis and dipeptidyl peptidase inhibition of N-(4-substituted-2,4-diaminobutanoyl)piperidines

In this paper, we report the synthesis of diastereomerically pure N-(4-substituted-2,4-diaminobutanoyl)piperidines. These compounds were prepared to investigate the influence of the 4-substitution on the dipeptidyl peptidase II (DPP II) activity and selectivity of the parent N-(2,4-diaminobutanoyl)piperidine. The (4S)-methyl compound showed subnanomolar inhibition, comparable with the parent compound. The (4R)-methyl group or bigger substituents decreased the activity.

β-isocupreidine-catalyzed Baylis-Hillman reaction of chiral N-Boc-α-amino aldehydes

β-Isocupreidine (β-ICD)-catalyzed Baylis-Hillman reaction of chiral N-Boc-α-amino aldehydes and 1,1,1,3,3,3-hexafluoroisopropyl acrylate (HFIPA) takes place without racemization and exhibits the match-mismatch relationship between the substrate and the catalyst. In the case of acyclic amino aldehydes, α,-substrates show excellent syn selectivity and high reactivity in contrast to L-substrates. On the other hand, in the case of cyclic amino aldehydes, D-substrates rather than L-substrates show excellent anti selectivity and high reactivity.

Heterocyclic Anti-Viral Compounds Comprising Metabolizable Moieties And Their Uses

The present invention relates to prodrugs and compositions thereof useful for treating or preventing Hepatitis C virus (HCV) infections. In particular, the present invention relates to prodrugs of substituted diphenyl-, diheteroaryl- and mixed phenyl heteroaryl substituted five-membered heterocycle compounds, compositions comprising the compounds and the use of such compounds and compositions to inhibit HCV replication and/or proliferation as a therapeutic approach towards the treatment and/or prevention of HCV infections in humans and animals.

Compounds, compositions and methods

Compounds useful for treating cellular proliferative diseases and disorders by modulating the activity of KSP are disclosed.