125700-05-2

Upstream product

• 13515-97-4 methyl 2-aminopropanoate monohydrochloride 
• 100-07-2 4-methoxy-benzoyl chloride 
• 2491-20-5 L-alanine methyl ester hydrochloride 
• 67-56-1 methanol 
• 99553-79-4 2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazole 
• 93709-64-9 (S)-2-(4-methoxybenzamido) propanoic acid 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 100-09-4 4-methoxybenzoic acid 
• 25616-13-1 alanine hydrochloride 

Downstream Products

• 125700-23-4 α-methoxy-N-(4-methoxybenzoyl)-alanine methyl ester 
• 108462-96-0 DL-N-(4-methoxybenzoyl)alanine 
• 93709-64-9 (S)-2-(4-methoxybenzamido) propanoic acid 
• 1220697-21-1 C₁₁H₁₅N₃O₃ 
• 1208130-64-6 N-((S)-1-((S)-1-(hydroxyamino)-5-(3-nitroguanidino)-1-oxopentan-2-ylamino)-1-oxopropan-2-yl)-4-methoxybenzamide 
• 1208130-72-6 (S)-methyl 2-((S)-2-(4-methoxybenzamido)propanamido)-5-(3-nitroguanidino) pentanoate 
• 159881-08-0 4-methyl-5-methoxy-2-(p-methoxyphenyl)oxazole 
• 99553-79-4 2-(4-methoxyphenyl)-4-methyl-5-oxo-4,5-dihydrooxazole 
• 154545-26-3 4-Methoxy-1-(4-methoxy-phenyl)-2,3,7-trioxa-bicyclo[2.2.1]hept-5-ene-5-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Rational Design of 2-Substituted DMAP- N-oxides as Acyl Transfer Catalysts: Dynamic Kinetic Resolution of Azlactones

A novel concept that conversion of chiral 2-substituted DMAP into its DMAP-N-oxide could significantly enhance the catalytic activity and still be used as an acyl transfer catalyst is presented. A new type of chiral 2-substituted DMAP-N-oxides, derived from l-prolinamides, has been rationally designed, facilely synthesized, and applied in the dynamic kinetic resolution of azlactones. Using simple MeOH as the nucleophile, various l-amino acid derivatives were produced in high yields (up to 98% yield) and enantioselectivities (up to 96% ee). Furthermore, α-deuterium labeled l-phenylalanine derivative was also obtained. Experiments and DFT calculations revealed that in 2-substituted DMAP-N-oxide, the oxygen atom acted as the nucleophilic site and the N-H bond functioned as the H-bond donor. High enantioselectivity of the reaction was governed by steric factors, and the addition of benzoic acid reduced the activation energy by participating in the construction of a H-bond bridge. The theoretical chemical study indicated that only when attack directions of the chiral catalyst were fully considered could the correct calculation results be obtained. This work paves the way for the utilization of the C2 position of the pyridine ring and the development of chiral 2-substituted DMAP-N-oxides as efficient acyl transfer catalysts.

Amide Synthesis by Nickel/Photoredox-Catalyzed Direct Carbamoylation of (Hetero)Aryl Bromides

Herein, we report a one-electron strategy for catalytic amide synthesis that enables the direct carbamoylation of (hetero)aryl bromides. This radical cross-coupling approach, which is based on the combination of nickel and photoredox catalysis, proceeds at ambient temperature and uses readily available dihydropyridines as precursors of carbamoyl radicals. The method's mild reaction conditions make it tolerant of sensitive-functional-group-containing substrates and allow the installation of an amide scaffold within biologically relevant heterocycles. In addition, we installed amide functionalities bearing electron-poor and sterically hindered amine moieties, which would be difficult to prepare with classical dehydrative condensation methods.

A chiral cobalt(II) complex catalyzed asymmetric formal [3+2] cycloaddition for the synthesis of 1,2,4-triazolines

A highly efficient catalytic asymmetric formal [3+2] cycloaddition reaction of 5-alkoxyoxazoles with azodicarboxylate compounds has been realized by a chiral N,N′-dioxide/Co(BF4)2·6H2O complex. A series of poly-substituted 1,2,4-triazolines compounds were obtained in moderate to excellent yields (70-99%) with excellent enantioselectivities (82-98% ee).

Novel L-arginine derivatives as aminopeptidase N inhibitors: design, chemistry, and pharmacological evaluation

Considering the important roles played in tumor, aminopeptidase N has been an appealing target for anti-tumor drug development. Here, a serial of novel aminopeptidase N inhibitors with L-arginine scaffold were designed, synthesized and evaluated for aminopeptidase N inhibitory activities. The preliminary anti-enzyme activity assay demonstrated that compounds 5e, 5h, 11e, 11g, and 11h showed comparable activities with the positive control bestatin, an approved aminopeptidase N inhibitor. In vitro anti-proliferation assay, compound 5f showed excellent activities against four kinds of tumor cells which overexpress aminopeptidase N. In vivo anti-metastasis assay, compounds 5f and 11g exhibited better activities than bestatin. So 5f and 11g should be lead compounds as novel aminopeptidase N inhibitors for further development.

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Titanium-catalyzed stereoselective synthesis of spirooxindole oxazolines

A regio-and stereoselective cyclization between isatins and 5-methoxyoxazoles has been developed using catalytic titanium (IV) chloride (10 or 20 mol %) to afford spiro[3,3'-oxindoleoxazolines] in excellent yield (up to 99%) and diastereoselectivity (dr >

SAR and molecular mechanism study of novel acylhydrazone compounds targeting HIV-1 CA

We synthesized a series of acylhydrazone compounds bearing naturally occurring amino acids' side chains as HIV assembly inhibitors. Biological evaluation indicated that the compounds had anti-SIV and capsid assembly inhibitory activities. The structure-activity relationship (SAR) study showed that compounds bearing proper aromatic side chains had potential antiviral activities. The molecular modeling experiments revealed the molecular mechanism that they could bind to CA in the same manner as CAP-1 and occupy two more grooves.

Design, synthesis and primary activity assay of bi- or tri-peptide analogues with the scaffold l-arginine as amino-peptidase N/CD13 inhibitors

A series of bi- or tri-peptide analogues with the scaffold l-arginine were designed, synthesized and evaluated for their inhibitory activities against amino-peptidase N (APN) and metalloproteinase-2 (MMP-2). The primary activity assay showed that all the compounds exhibited higher inhibitory activities against APN than MMP-2. Within this series, compounds C6 and C7 (IC50 = 4.2 and 4.3 μM) showed comparable APN inhibitory activities with the positive control bestatin (IC50 = 3.8 μM).

Probing the efficiency of N-heterocyclic carbene promoted O- to C-carboxyl transfer of oxazolyl carbonates

(Chemical Equation Presented) Screening of a range of azolium salts, bases and solvents for reactivity indicates that triazolinylidenes, generated in situ with KHMDS in THF, promote the Steglich rearrangement of oxazolyl carbonates with high catalytic efficiency (typical reaction time 5 min at 1.5 mol % NHC). This protocol shows wide substrate applicability, even allowing the efficient generation of vicinal quaternary centers. An improved experimental procedure is also described that allows a simplified one-pot reaction protocol to be employed with similarly high catalytic efficiency.

INDIRECT ELECTROCHEMICAL α-METHOXYLATION OF N-ACYL AND N-CARBOALKOXY α-AMINO ACID ESTERS AND APPLICATION AS CATIONIC GLYCINE EQUIVALENTS

Indirect electrochemical methoxylation of N-acyl and N-carboalkoxy α-amino acid esters in α-position to nitrogen is possible, if chloride is used as mediator.The course of the reaction depends upon the protecting group as well as upon the amino acid side-chain.Increased electron withdrawing effects of the protecting group are accelerating the reaction.On the other hand aliphatic side-chains are diminishing the reactivity.High chloride ion concentrations improve the current yields surprisingly strong.