5426-73-3

Basic information

• Product Name: N-phenylphenylalaninamide
• Synonyms: benzenepropanamide, alpha-amino-N-phenyl-
• CAS NO: 5426-73-3
• Molecular Formula: C₁₅H₁₆N₂O
• Molecular Weight: 240.3003
• Mol File: 5426-73-3.mol

Chemical Properties

• Boiling Point: 465°C at 760 mmHg
• Flash Point: 235°C
• Density: 1.179g/cm³
• Vapor Pressure: 7.96E-09mmHg at 25°C
• Refractive Index: 1.636
• CAS DataBase Reference: N-phenylphenylalaninamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-phenylphenylalaninamide(5426-73-3)
• EPA Substance Registry System: N-phenylphenylalaninamide(5426-73-3)

Safety Data

• Hazardous Substances Data: 5426-73-3(Hazardous Substances Data)

Upstream product

• 108-86-1 bromobenzene 
• 17193-31-6 (R,S)-2-amino-3-phenylpropionamide 
• 5241-58-7 L-Phenylalanine amide 
• 108-90-7 chlorobenzene 
• 591-50-4 iodobenzene 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 66003-76-7 Diphenyliodonium triflate 
• 852331-92-1 Boc-Phe-OH 
• 1161-13-3 N-Cbz-L-Phe 
• 62-53-3 aniline 
• 591-19-5 m-Bromoaniline 
• 1240522-91-1 C₂₀H₂₃BrN₂O₃ 
• 100-52-7 benzaldehyde 
• 3129-98-4 (R)-benzylidene-(1-phenylethyl)amine 

Downstream Products

• 5426-73-3 L-phenylalanineanilide 
• 16876-72-5 (R)-2-amino-N,3-diphenyl-propanamide 
• 1020151-02-3 C₃₀H₃₄N₂O₃ 
• 113035-40-8 N²-<(tert-butoxy)carbonyl>-L-phenylalanine phenylamide 
• 215670-78-3 (S)-3-phenyl-5-benzylimidazolidine-2,4-dione 
• 1401206-52-7 C₁₉H₁₉N₃OS 
• 1378237-00-3 Boc-Aib-Phe-NHPh 
• 1378236-98-6 H-Pro-D-Pro-Aib-Phe-NHPh 
• 1378237-01-4 Boc-Pro-D-Pro-Aib-Phe-NHPh 
• 1378236-99-7 H-Aib-Phe-NHPh 

Relevant articles and documents

Pd-Catalysed oxidative carbonylation of α-amino amides to hydantoins under mild conditions

The first example of palladium-catalysed oxidative carbonylation of unprotected α-amino amides to hydantoins is described here. The selective synthesis of the target compounds was achieved under mild conditions (1 atm of CO), without ligands and bases. The catalytic system overrode the common reaction pathway that usually leads instead to the formation of symmetrical ureas.

Design, synthesis, and insecticidal activities of novel diamide derivatives with alpha-amino acid subunits

A series of diamide derivatives containing α-amino acids were designed and synthesized. These compounds were evaluated for their insecticidal activities against Plutella xylostella, Mythimna separate, Myzus persicae, and Tetranychus cinnabarinus. Most of the title compounds containing an l-phenylglycine skeleton were endowed with good activities at the concentration of 500 mg·L?1. Compounds (R)-A6 showed a potential value for further optimization as an insecticidal lead with the LC50 value of 86.8 mg·L?1.

Bifunctional Naphthoquinone Aromatic Amide-Oxime Derivatives Exert Combined Immunotherapeutic and Antitumor Effects through Simultaneous Targeting of Indoleamine-2,3-dioxygenase and Signal Transducer and Activator of Transcription 3

Indoleamine-2,3-dioxygenase 1 (IDO1) and signal transducer and activator of transcription 3 (STAT3) are important targets in the tumor microenvironment for cancer therapy. In the present study, a set of naphthoquinone aromatic amide-oxime derivatives were designed, which stimulated the immune response via IDO1 inhibition and simultaneously displayed powerful antitumor activity against three selected cancer cell lines through suppressing STAT3 signaling. The representative compound 8u bound effectively to IDO1, with greater inhibitory activity relative to the commercial IDO1 inhibitor 4-amino-N-(3-chloro-4-fluorophenyl)-N′-hydroxy-1,2,5-oxadiazole-3-carboximidamide (IDO5L) in addition to the efficient suppression of nuclear translocation of STAT3. Consistently, in vivo assays demonstrated a higher antiproliferative activity of compound 8u in both wild-type B16-F10 isograft tumors and an athymic HepG2 xenograft model relative to 1-methyl-l-tryptophan (1-MT) and doxorubicin (DOX). This bifunctional compound with dual immunotherapeutic and anticancer efficacy may represent a new generation of highly efficacious drug candidates for cancer therapy.

Enantioseparation of Sulfoxides and Nitriles by Inclusion Crystallization with Chiral Organic Salts Based on l-Phenylalanine

Enantioselective inclusion of aromatic sulfoxides and nitriles was achieved in a host framework created by organic salts comprising achiral benzoic acids and a chiral primary amine (1a) derived from l-phenylalanine. Tuning of the combined achiral acid component successfully changed the chiral recognition ability of the organic salts. The guest molecules were hydrogen-bonded to form three-component inclusion crystals, and the enantiomers of nitriles and sulfoxides were separated with high selectivity up to 92 and 98 % ee. As far as we know, this is the first example of the enantioseparation of non-functionalized aromatic nitriles.

For the chiral nitrogen is mixed ligand compound and its preparation method and application (by machine translation)

The invention belongs to the technical field of organic chemistry, discloses a method for the preparation of the chiral nitrogen is mixed ligand compound. A structure of formula (1) is shown. Preparation method in accordance with the following steps: in the 10 - 50 °C lower dichloromethane solvent condensing agent employed in the DCC, DMAP catalyst aniline connected to phenylalanine, reaction time 3h - 48h; by using silica gel column, separation from the intermediate product with a protecting group; acid protecting group is removed, the reaction time is 30 min - 24 h, to obtain the chiral shan an intermediate; the intermediate with the benzaldehyde to Schiff base synthesis and reduction reaction, to obtain the target product. This invention synthetic chiral aza ligand compound, but also for the Schiff base-reducing compounds, but a part of the Schiff base of the defect, in the stability and flexibility are very good in, and because of its chiral structure and hydrogen bond role, has molecular recognition and coordination capacity, in which the main object of chemical and the coordination chemistry in broad application prospects. (by machine translation)

Discovery of dehydroabietic acid sulfonamide based derivatives as selective matrix metalloproteinases inactivators that inhibit cell migration and proliferation

A series of dehydroabietic acid (DHAA) dipeptide derivatives containing the sulfonamide moiety were designed, synthesized and evaluated for inhibition of MMPs as well as the effects of in vitro cell migration. These compounds exhibited relatively good inhibition activity against MMPs with IC50 values in low micromolar range. A docking study of the most active compound 8k revealed key interactions between 8k and MMP-3 in which the sulfonamide moiety and the dipeptide group were important for improving activity. It is noteworthy that further antitumor activity screening revealed that some compounds exhibited better inhibitory activity than the commercial anticancer drug 5-FU. In particular, compound 8k appeared to be the most potent compound against the HepG2 cell line, at least partly, by inhibition of the activity of MMP-3 and apoptosis induction. The treatment of HepG2 cells with compound 8k resulted in inhibition of in vitro cell migration through wound healing assay and G1 phase of cell cycle arrested. In addition, 8k-induced apoptosis was significantly facilitated in HepG2 cells. Thus, we conclude that DHAA dipeptide derivatives containing the sulfonamide moiety may be the potential MMPs inhibitors with the ability to suppress cells migration.

Synthetic process of chiral N-aromatic amino acid amide

Chiral N-aromatic amino acid amide is a core structure fragment of drugs and an intermediate of the drugs. Only if the chiral structure of the product is not required by special raw materials such aryl halide activated by functional groups of nitryl and t

Synthesis and antitumor activities of novel dipeptide derivatives derived from dehydroabietic acid

A series of dipeptide derivatives from dehydroabietic acid were designed and synthesized as novel antitumor agents. The antitumor activities screening indicated that many compounds showed moderate to high levels of inhibition activities against NCI-H460, HepG2, SK-OV-3, BEL-7404, HeLa and HCT-116 cancer cell lines and that some displayed more potent inhibitory activities than commercial anticancer drug 5-fluorouracil. The mechanism of representative compound 7b was studied by AO/EB staining, Hoechst 33258 staining, JC-1 mitochondrial membrane potential staining, TUNEL assay, DNA ladder assay and flow cytometry, which exhibited that the compound could induce apoptosis in HeLa cells. Further investigation showed that compound 7b induced apoptosis of HeLa cells through a mitochondrial pathway.

Ruthenium-catalyzed N-alkylation of amines with alcohols under mild conditions using the borrowing hydrogen methodology

Using a simple amino amide ligand, ruthenium-catalyzed one-pot alkylation of primary and secondary amines with simple alcohols was carried out under a wide range of conditions. Using the alcohol as solvent, alkylation was achieved under mild conditions, even as low as room temperature. Reactions occurred with high conversion and selectivity in many cases. Reactions can also be carried out at high temperatures in organic solvent with high selectivity using stoichiometric amounts of the alcohol.