64501-87-7

Basic information

• Product Name: N-(4-NITROPHENYLSULFONYL)-L-PHENYLALANINE
• Synonyms: N-(4-NITROPHENYLSULFONYL)-L-PHENYLALANINE;Nitrophenylsulfonylphenylalanine;N-(4-Nitrophenylsulfonyl)-L-phenylalanine
• CAS NO: 64501-87-7
• Molecular Formula: C₁₅H₁₄N₂O₆S
• Molecular Weight: 350.35
• Mol File: 64501-87-7.mol
• Article Data: 11

Chemical Properties

• Melting Point: 169 °C
• Boiling Point: 582.7 °C at 760 mmHg
• Flash Point: 306.2 °C
• Appearance: /
• Density: 1.456 g/cm³
• Refractive Index: -19 ° (C=3, Acetone)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: 3.15±0.10(Predicted)
• CAS DataBase Reference: N-(4-NITROPHENYLSULFONYL)-L-PHENYLALANINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-NITROPHENYLSULFONYL)-L-PHENYLALANINE(64501-87-7)
• EPA Substance Registry System: N-(4-NITROPHENYLSULFONYL)-L-PHENYLALANINE(64501-87-7)

Safety Data

• Hazardous Substances Data: 64501-87-7(Hazardous Substances Data)

Usage

General Description

N-(4-Nitrophenylsulfonyl)-L-phenylalanine is a chemical compound that combines the amino acid L-phenylalanine with a nitrophenylsulfonyl group. It is commonly used as a reagent in the synthesis of peptides and proteins, particularly in solid-phase peptide synthesis. N-(4-NITROPHENYLSULFONYL)-L-PHENYLALANINE is known for its ability to selectively protect the carboxyl group of amino acids, allowing for the controlled assembly of peptide chains. It is also used in the study of enzyme kinetics and catalysis, as well as in the development of pharmaceuticals and biologically active compounds. Overall, N-(4-Nitrophenylsulfonyl)-L-phenylalanine plays a crucial role in the field of organic chemistry and biochemistry.

Upstream product

• 63-91-2 L-phenylalanine 
• 98-74-8 4-Nitrobenzenesulfonyl chloride 
• 3182-95-4 L-Phenylalaninol 
• 150-30-1 Phenylalanine 

Downstream Products

• 133978-59-3 2-{[(4-aminophenyl)sulfonyl]amino}-3-phenylpropanoic acid 

Relevant articles and documents

Synthesis, characterization and in vitro antitrypanosomal activities of new carboxamides bearing quinoline moiety

The reported toxicities of current antitrypanosomal drugs and the emergence of drug resistant trypanosomes underscore the need for the development of new antitrypanosomal agents. We report herein the synthesis and antitrypanosomal activity of 24 new amide derivatives of 3-aminoquinoline, bearing substituted benzenesulphonamide. Nine of the new derivatives showed comparable antitrypanosomal activities at IC50 range of 1–6 nM (melarsoprol 5 nM). Compound 11n and 11v are more promising antitrypanosomal agents with IC50 1.0 nM than the rest of the reported derivatives. The novel compounds showed satisfactory predicted physico-chemical properties including oral bioavailability, permeability and transport properties.

Development of Piperazinediones as dual inhibitor for treatment of Alzheimer's disease

Novel multifunctional 3,6-Diphenyl-1,4-bis(phenylsulfonyl)piperazine-2,5-dione derivatives were designed and synthesized for the treatment of Alzheimer's disease (AD). The designed scaffold has blood brain barrier penetrating ability, acetylcholinesterase (AChE) and matrix metalloproteinase-2 (MMP-2) inhibition potential. Compounds 52 and 46 showed very significant inhibition against AChE, IC50 = 32.45 ± 0.044, 28.65 ± 0.029, BuChE, IC50 = 157.95 ± 0.264, 160.58 ± 0.082 and MMP-2, IC50 = 36.83 ± 0.015, 19.57 ± 0.005 (nM). In the enzyme kinetics study, lead molecule 46 showed non-competitive inhibition of AChE with Ki = 7 nM and competitive inhibition of MMP-2 with Ki = 20 nM. Compounds 52 and 46 inhibited AChE-induced Aβ aggregation at 20 μM. The compounds also exhibited in-vitro antioxidant potential in DPPH assay. Further, compound 46 was found to be a promising neuroprotective agent in MC65 cells. Lead molecule 46 significantly enhanced working memory in scopolamine induced amnesia animal model at dose of 5 mg/kg dose. The mitochondrial membrane potential was restored in animals when treated with compounds 52 and 46.

New carboxamide derivatives bearing benzenesulphonamide as a selective COX-II inhibitor: Design, synthesis and structure-activity relationship

Sixteen new carboxamide derivatives bearing substituted benzenesulphonamide moiety (7a-p) were synthesized by boric acid mediated amidation of appropriate benzenesulphonamide with 2-amino-4-picoline and tested for anti-inflammatory activity. One compound 7c showed more potent anti-inflammatory activity than celecoxib at 3 h in carrageenan-induced rat paw edema bioassay. Compounds 7g and 7k also showed good anti-inflammatory activity comparable to celecoxib. Compound 7c appeared selectivity index (COX-2/COX-1) better than celecoxib. Compound 7k appeared selectivity index (COX-2/COX-1) a little higher than the half of celecoxib while compound 7g is non-selective for COX-2. The LD50 of compounds 7c, 7g and 7k were comparable to celecoxib.