182883-41-6

Basic information

• Product Name: Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI)
• Synonyms: FMOC-L-NORTYR;(S)-[(9H-FLUOREN-9-YLMETHOXYCARBONYLAMINO)]-(4-HYDROXY-PHENYL)-ACETIC ACID;Fmoc-L-4-Hydroxyphenylglycine
• CAS NO: 182883-41-6
• Molecular Formula: C23H19 N O5
• Molecular Weight: 389.4
• Mol File: 182883-41-6.mol

Chemical Properties

• Appearance: /
• Storage Temp.: 2-8°C
• CAS DataBase Reference: Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI)(182883-41-6)
• EPA Substance Registry System: Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)- (9CI)(182883-41-6)

Safety Data

• Hazardous Substances Data: 182883-41-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Synthesis:
Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)(9CI) is used as a building block in the pharmaceutical industry for the development of drugs and medicines. Its unique structure and functional groups make it suitable for chemical reactions and biological interactions, contributing to the creation of new therapeutic agents.
Used in Chemical Reactions:
In the chemical industry, Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)(9CI) is employed in various chemical reactions due to its reactive functional groups. Its properties allow it to participate in a wide range of processes, making it a valuable component in the synthesis of various compounds.
Used in Biological Interactions:
Due to its chiral nature and specific spatial arrangement, Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)(9CI) is utilized in biological interactions, where its stereochemistry plays a crucial role in determining its interactions with biological targets. This makes it a valuable tool in the study of enzyme inhibition, receptor binding, and other biological processes.
Used in Research and Development:
In the field of scientific research, Benzeneacetic acid, a-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-4-hydroxy-,(S)(9CI) is employed as a research tool to explore its potential applications and properties. Its unique structure and functional groups make it an interesting subject for studies in organic chemistry, medicinal chemistry, and other related disciplines.

Upstream product

• 82911-69-1 N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide 
• 32462-30-9 (S)-hydroxyphenylglycine 

Relevant articles and documents

SAR evolution towards potent C-terminal carboxamide peptide inhibitors of Zika virus NS2B-NS3 protease

Zika virus (ZIKV) is a member of the Flaviviridae family that can cause neurological disorders and congenital malformations. The NS2B-NS3 viral serine protease is an attractive target for the development of new antiviral agents against ZIKV. We report here a SAR study on a series of substrate-like linear tripeptides that inhibit in a non-covalent manner the NS2B-NS3 protease. Optimization of the residues at positions P1, P2, P3 and of the N-terminal and C-terminal portions of the tripeptide allowed the identification of inhibitors with sub-micromolar potency with phenylglycine as arginine-mimicking group and benzylamide as C-terminal fragment. Further SAR exploration and application of these structural changes to a series of peptides having a 4-substituted phenylglycine residue at the P1 position led to potent compounds showing double digit nanomolar inhibition of the Zika protease (IC50 = 30 nM) with high selectivity against trypsin-like proteases and the proteases of other flavivirus, such as Dengue 2 virus (DEN2V) and West Nile virus (WNV).

Beyond Basicity: Discovery of Nonbasic DENV-2 Protease Inhibitors with Potent Activity in Cell Culture

The viral serine protease NS2B-NS3 is one of the promising targets for drug discovery against dengue virus and other flaviviruses. The molecular recognition preferences of the protease favor basic, positively charged moieties as substrates and inhibitors, which leads to pharmacokinetic liabilities and off-target interactions with host proteases such as thrombin. We here present the results of efforts that were aimed specifically at the discovery and development of noncharged, small-molecular inhibitors of the flaviviral proteases. A key factor in the discovery of these compounds was a cellular reporter gene assay for the dengue protease, the DENV2proHeLa system. Extensive structure-activity relationship explorations resulted in novel benzamide derivatives with submicromolar activities in viral replication assays (EC50 0.24 μM), selectivity against off-target proteases, and negligible cytotoxicity. This structural class has increased drug-likeness compared to most of the previously published active-site-directed flaviviral protease inhibitors and includes promising candidates for further preclinical development.

Discovery of Nanomolar Dengue and West Nile Virus Protease Inhibitors Containing a 4-Benzyloxyphenylglycine Residue

The dengue virus (DENV) and West Nile Virus (WNV) NS2B-NS3 proteases are attractive targets for the development of dual-acting therapeutics against these arboviral pathogens. We present the synthesis and extensive biological evaluation of inhibitors that