16859-11-3

Upstream product

• 17463-57-9 N-(succinimid-1-ylcarbonyl)-L-phenylalanine methyl ester 
• 5070-13-3 bis-(p-nitrophenyl) carbonate 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 142311-87-3 (S)-2-Methylsulfanylcarbonylamino-3-phenyl-propionic acid methyl ester 
• 201230-82-2 carbon monoxide 
• 51987-73-6 (S)-2-tert-butoxycarbonylamino-3-phenyl-propionic acid methyl ester 
• 63-91-2 L-phenylalanine 
• 40203-94-9 methyl (S)-2-isocyanato-3-phenylpropanoate 
• 124-38-9 carbon dioxide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1256930-64-9 (S)-methyl 2-(3-hydroxyureido)-3-phenylpropanoate 
• 530-62-1 1,1'-carbonyldiimidazole 

Downstream Products

• 13589-08-7 (S,S)-N,N'-bis(1-carboxy-2-phenylethyl)urea 
• 96943-03-2 (S)-2-((S)-4-benzyl-2,5-dioxoimidazolidin-1-yl)-3-phenylpropanoic acid 
• 1244610-62-5 (S,S)-N-hydroxy-2-[3-(1-hydroxycarbamoyl-2-phenylethyl)-ureido]-3-phenyl-propionamide 

Relevant academic research and scientific papers

Efficient synthesis of ureas by direct palladium-catalyzed oxidative carbonylation of amines

A general synthesis of symmetrically disubstituted ureas and trisubstituted ureas by direct Pd-catalyzed oxidative carbonylation of primary amines or of a mixture of a primary and a secondary amine, respectively, with unprecedented catalytic efficiencies for this kind of process, is reported. Reactions are carried out at 90-100 °C in DME as the solvent in the presence of PdI 2 in conjunction with an excess of KI as the catalytic system and under 20 atm of a 4:1 mixture of CO and air. In some cases, working in the presence of an excess of CO2 (40 atm) in addition to CO and air (60 atm total) had a beneficial effect on substrate reactivity and product yield. Cyclic five-membered and six-membered ureas were easily formed from primary diamines. The methodology has been successfully applied to the synthesis of pharmacologically active ureas, such as those deriving from α-amino esters or urea NPY5RA-972, a potent antagonist of the neuropeptide Y5 receptor.

Preparation of Carbodiimides with One-Handed Axial Chirality

The axial chirality of carbodiimide was proposed in 1932, but the synthesis of carbodiimide with one-handed axial chirality has not been achieved because of the low barrier of racemization. This work presents a strategy to use a conformationally restrained cyclic structure for creating carbodiimides whose biases of the axial chirality (labeled as SNCN/RNCN) are higher than 100:1, as determined by vibrational circular dichroism spectroscopy and density functional theory calculations.

Peptide dendrimers with designer core for directed self-assembly

A series of designer peptide dendrimers with urea and urea-triazole cores were synthesized. Urea cored dendrimers assembled into fibrillar morphology, while dendrimers with urea-triazole core assembled into vesicular morphology. The core-dependent self-as

A One-Pot Synthesis of Symmetrical and Unsymmetrical Dipeptide Ureas

We describe a flexible and high yielding synthesis of 1,3-disubstituted ureas that allows for the construction of both symmetrical and unsymmetrical dipeptide ureas, including easy access to 13C-labelled ureas, from amino acids and carbon dioxide at atmospheric pressure. We describe a flexible and high yielding synthesis of 1,3-disubstituted ureas, that allows for the construction of both symmetrical and unsymmetrical dipeptide ureas, including easy access to 13C labelled ureas, from amino acids and carbon dioxide at atmospheric pressure.

Design, synthesis and biological evaluation of novel amino acid ureido derivatives as aminopeptidase N/CD13 inhibitors

A series of amino acid ureido derivatives as aminopeptidase N (APN/CD13) inhibitors were synthesized and evaluated for their APN inhibitory activities and anti-cancer effects. The results showed that most of these amino acid ureido derivatives exhibited good inhibition against APN, several of which were better than Bestatin. The most active compound 12j (IC50 = 1.1 μM, compared with Bestatin IC50 = 8.1 μM) not only possessed much better APN inhibitory activity and anti-proliferation effect on cancer cells, but also exhibited significant block effect of human cancer cell invasion compared with the positive control, Bestatin. These amino acid ureido derivatives could be possibly developed as new APN inhibitors for cancer chemotherapy in the future.

Semicarbazones from N-hydroxyureas and amines: A novel entry in the reactivity of the acyl nitroso group

The condensation of carbamoyl nitroso compounds, obtained by oxidation of N-hydroxyureas, with amines unexpectedly afforded semicarbazones (aka carbamoyl hydrazones). Although the substitution of the nitrosyl moiety might compete to afford the correspondi

Triflic anhydride-mediated synthesis of oxazoles

N-Acyl amino acid esters undergo triflic anhydride-mediated cyclodehydration to form oxazoles and bisoxazoles in a simple one-pot transformation.

Conversion of carbonimidodithioates into unsymmetrical Di- and Tri- substituted ureas including urea dipeptides

Selective hydrolysis of carbonimidodithioates (3) leads to the thiocarbamates (4), which can be easily transformed to the unsymmetrical ureas (5) by treatmeat with the appropriate amines. This constitutes a synthesis of ureas without the use of phosgene o

Synthesis of N,N′-carbonyl-bis-amino acids and N,N′-carbonyl-bis-peptides

A new method for the preparation of N,N′-carbonyl-bis-amino acid esters by reaction of bis(4-nitrophenyl)carbonate with amino acid esters is described. When the carbonate reacts with two equivalents of a peptide ester, N,N′-carbonyl-bis(peptide ester) is obtained but, a hydantoin derivative is formed as a side product. The hydantoin derivative is a major product, when equimolar amounts are allowed to react. Usefulness of this method for preparation of larger N,N′carbonyl-bis-peptides is demonstrated by the synthesis of the respective product from C-terminal hexapeptide of Substance P linked to the Merrifield resin.

LATENT INHIBITORS. PART 4. IRREVERSIBLE INHIBITION OF DIHYDRO-OROTATE DEHYDROGENASE BY HYDANTOINS DERIVED FROM AMINO ACIDS

Hydantoins and ureas derived from α-amino acids are shown to interact with dihydro-orotate dehydrogenase from Clostridium (Zymobacterium) oroticum, chiefly as weak competitive inhibitors but that the hydantoin derived from phenylalanine, 5-benzyl-3-(1-car