116366-27-9

Usage

Uses

Used in Pharmaceutical Industry:
N-BOC-4-NITRO-L-PHENYLALANINE-T-BUTYL ESTER is used as a synthetic intermediate for the production of (2S)-2-Amino-3-(4-morpholin-4-ylphenyl)propanoic Acid (A618690), which is a compound with potential pharmaceutical applications.
Used in Chemical Synthesis:
N-BOC-4-NITRO-L-PHENYLALANINE-T-BUTYL ESTER is also used as a synthetic intermediate in the synthesis of Melphalan (M216900), an antineoplastic drug used for the treatment of various types of cancer. It serves as an impurity in the production process, which may require further purification to ensure the quality and efficacy of the final product.

InChI:InChI=1/C18H26N2O6/c1-17(2,3)25-15(21)14(19-16(22)26-18(4,5)6)11-12-7-9-13(10-8-12)20(23)24/h7-10,14H,11H2,1-6H3,(H,19,22)/t14-/m0/s1

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 33305-77-0 Boc-Phe(p-NO₂)-OH 
• 36805-97-7 N,N-dimethylformamide di-tert-butyl acetal 
• 63-91-2 L-phenylalanine 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 115-11-7 isobutene 
• 98946-18-0 tert-Butyl 2,2,2-trichloroacetimidate 

Downstream Products

• 3223-07-2 melphalan hydrochloride 
• 166888-39-7 (S)-N-[(tert-butyloxy)carbonyl]-[4-thioureaphenyl]alanine tert-butyl ester 
• 116366-32-6 L-4-nitrophenylalanine tert-butyl ester 

Relevant academic research and scientific papers

PTERIDINE DERIVATIVES AS POLO-LIKE KINASE INHIBITORS USEFUL IN THE TREATMENT OF CANCER

Compound of formula (I) are inhibitors of Polo-like kinases (PLKs), and are useful in treatment of cell proliferative diseases: wherein R1 and R2 are hydrogen, or an optionally substituted (C1-C6)alkyl, (C2- Cs

Aminoacid derivatives as no synthase inhibitors

Compounds of formula (I) and salts, esters and amides thereof, wherein R1 is a C1-6 straight or branched chain alkyl group, a C3-6 cycloalkyl group, a thiol group optionally substituted by a C1-6 alkyl group, or an amino group optionally substituted by one or two alkyl or alkenyl groups; R2 is H, C1-7 straight or branched chain alkyl, C3-6 cycloalkyl, C2-7 alkenyl or benzyl; A is a 5 or 6 membered aromatic carbocyclic or heterocyclic ring which may optionally be substituted by one or more suitable substituents such as C1-6 alkyl, C1-6 alkoxy, hydroxy, halo, nitro, cyano, trifluoro C1-6 alkyl, amino, C1-6 alkylamino or di C1-6 alkylamino; r is 0, 1 or 2; their use in medicine and in particular for conditions requiring inhibition of the NO Synthase enzyme, pharmaceutical formulations and processes for the preparation thereof are disclosed. STR1

Asymmetric synthesis of conformationally restricted L-arginine analogues as active site probes of nitric oxide synthase

Using the catalytic asymmetric sharpless carbamate aminohydroxylation, conformationally restricted L-arginine and L-homoarginine derivatives (5-8) were prepared in good enantiomeric excess to investigate the binding requirements of L-arginine-based compounds with nitric oxide synthase. The L- arginine derivatives (5 and 6) inhibited both the inducible and neuronal isoforms of nitric oxide synthase with little isoform selectivity (5, IC50 = 42 and 144 μM, 6, 8 and 12 μM, respectively). The guanidine-containing compound (5) did not act as a nitric oxide producing substrate for nitric oxide synthase. The ability of these compounds to interact with the enzyme supports the idea that L-arginine-based inhibitors bind to the enzyme in a folded conformation. The L-homoarginine derivatives (7 and 8) did not interact with the enzyme as either substrates or inhibitors. The two-carbon L-arginine homologue (9), prepared from L-phenylalanine, demonstrated the greatest isoform selective inhibition of the compounds examined (IC50(iNOS) = 19 and IC50(nNOS) = 147 μM, IC50(nNOS)/IC50i(NOS) = 7.7). These results suggest isoform selective inhibition may be related to the folded conformations required for binding of these higher L-arginine homologues.