21171-98-2

Upstream product

• 121632-87-9 tert-butyl N-[(1S)-1-benzyl-2-oxo-2-(4-toluidino)ethyl]carbamate 
• 106-49-0 p-toluidine 
• 20998-88-3 (2S)-2-benzyloxyformamido-N-(4-methylphenyl)-3-phenylpropanamide 
• 624-31-7 4-tolyl iodide 
• 5241-58-7 L-Phenylalanine amide 
• 106-38-7 para-bromotoluene 
• 32150-91-7 phthaloyl-L-phenylalanyl chloride 
• 65864-22-4 (S)-2-amino-3-phenylpropionamide hydrochloride 
• 5123-55-7 Nα-phthaloyl-L-phenylalanine 
• 247179-01-7 2-tert-butoxycarbonylamino-3-phenyl-propionic acid isobutyl ester 
• 13734-34-4 N-tert-butoxycarbonyl-L-phenylalanine 
• 63-91-2 L-phenylalanine 

Downstream Products

• 123965-45-7 N-benzoylthiocarbamoyl-phenylalanine p-toluidide 
• 479191-68-9 (2S)-2-[(1H-1,2,3-benzotriazol-1-ylmethyl)amino]-N-(4-methylphenyl)-3-phenylpropanamide 
• 479191-76-9 (2S,5S)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one 
• 479191-75-8 (2R,5S)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one 
• 1020151-03-4 C₃₁H₃₆N₂O₃ 
• 76319-08-9 (S)-5-benzyl-3-(p-tolyl)imidazolidine-2,4-dione 
• 433219-34-2 (2S)-N¹-(4-methylphenyl)-3-phenyl-1,2-propanediamine 
• 479191-79-2 (2R,5S)-1-(1H-1,2,3-benzotriazol-1-ylmethyl)-5-benzyl-3-(4-methylphenyl)-2-phenyltetrahydro-4H-imidazol-4-one 

Relevant academic research and scientific papers

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.

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.

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.

Caproamide derivatives, its preparation method, intermediate and application

The invention discloses a caproamide derivative represented by formula A or a pharmaceutically acceptable salt thereof, wherein R1 is H or halogen; R2 is halogen, or C1-C4 alkyl, C1-C4 alkoxy, or a C3-C7 heterocyclic ring, the number of heteroatom in the heterocyclic ring is 1-3, and the heteroatom is nitrogen and/or oxygen; R0 is benzyl, substituted benzyl or C4 alkyl, and a substituent of substituted benzyl is C1-C3 alkyl. The invention also discloses a preparation method, an intermediate and an application of the caproamide derivative. The caproamide derivative provided by the invention has effective and better antibacterial function, and has higher application value in the medical field.

Synthesis of chiral amino acid anilides by ligand-free copper-catalyzed selective N-arylation of amino acid amides

An atom-economic, practical and cost-effective protocol for synthesis of chiral amino acid anilides via ligand-free copper-catalyzed selective C-N cross coupling of chiral amino acid amides and aryl halides, hetereoaryl halides and a vinyl bromide has been developed. No racemization occurred during the C-N coupling. A plausible mechanism is proposed. Copyright

Enantioselective nickel-catalyzed conjugate addition of dialkylzinc to chalcones using chiral α-amino amides

A series of α-amino amides derived from natural amino acids (alanine, valine, phenylalanine, isoleucine, and phenylglycine) have been synthesized and fully characterized. Their Ni(II) complexes prepared from Ni(acac)2 catalyze the enantioselective conjugate addition of diethylzinc to chalcones in high yields and in good enantioselectivities (up to 84%). The side chain of the amino acid and the substituents in the amide nitrogen govern the enantioselectivity of the catalytic process.

Synthesis of rupestonic acid amide derivatives and their in vitro activity against type A3 and B flu virus and herpes simplex I and II

Derivatives of rupestonic acid (5a-e) were synthesized and evaluated preliminarily at the National Center for Drug Screening (PRC) for antiviral activity against type A3 and B flu virus and HSV-I and HSV-II in order to improve the biological ac

Facile N-Derivatization of α-Amino Esters and Amides via Benzotriazolylmethyl Derivatives

α-(N-Substituted amino)esters were prepared in a two-step procedure from available unsubstituted α-amino esters. α-Amino esters are first converted into the corresponding N-benzotriazolylmethyl derivatives; in the second step, the benzotriazole group is substituted by various nucleophiles with or without the presence of a Lewis acid to give substituted α-amino esters in high overall yield under mild conditions with no signs of racemization. Boc-protected amino acids were converted into α-amino amides; subsequent deprotection allowed the conversion into N-substituted derivatives analogously to the α-amino esters, without racemization in high yields under mild conditions.

Novel syntheses of enantiopure hexahydroimidazo[1,5-b]isoquinolines and tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones via iminium cation cyclizations

Condensations of chiral diamines 11a-c with benzotriazole and formaldehyde gave benzotriazolyl intermediates 12a-c; similar condensations of α-amino-amides 10a-c with benzotriazole and paraformaldehyde gave 14a-c. Subsequent treatment of 12a-c and 14a-c with AlCl3 led to enantiopure tricyclic 1,2,3,5,10,10a-hexahydroimidazo[1,5-b]isoquinolines 1a-c and 2,3,10,10a-tetrahydroimidazo[1,5-b]isoquinolin-1(5H)-ones 15a-c, respectively, via Lewis acid promoted iminium cation cyclizations.

Syntheses of optically active tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones and hexahydroimidazo[1,2-a]pyridin-2(3H)-ones

The reactions of (2S)-2-amino-2-substituted-N-(4-nitrophenyl)acetamides 16a-c, succindialdehyde (13), and benzotriazole afforded enantiopure (3S,5R,7aR)-5-(1H-1,2,3-benzotriazol-1-yl)-3-substituted-1-(4-nitrophenyl) tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones 17a-c, which were converted by sodium borohydride into (3S,7aR)-3-substituted-1-(4-nitrophenyl)tetrahydro-1H-pyrrolo[1, 2-a]imidazol-2-ones 18a-c. Chiral (2S)-2-amino-2-substituted-N-(4-methylphenyl)acetamides 12a-d, easily prepared in two steps from N-Boc-α-amino acids 10a-d, similarly reacted with glutaraldehyde (20) and benzotriazole to generate 5-benzotriazolyl-3-substituted-hexahydroimidazo[1,2-a]pyridin 2(3H)-ones 21a-d, which were converted by sodium borohydride directly into optically active 3-substituted-hexahydroimidazo[1,2-a]pyridin-2(3H)-ones 22a-d.