129101-25-3

Usage

Uses

Used in Pharmaceutical Research and Development:
Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-4-fluorois utilized as a compound in pharmaceutical research and development for its potential use in drug design. The protective group and the presence of a fluorine atom in the molecule can contribute to the development of new drugs with improved properties and biological activities.
Used in Peptide Synthesis:
In the field of peptide synthesis, Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-4-fluorois employed as a building block for the synthesis of peptides. The protective N-[(1,1-dimethylethoxy)carbonyl] group helps to prevent unwanted side reactions during the synthesis process, ensuring the formation of the desired peptide sequence.
Used in Drug Design:
Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-4-fluorois also used in drug design to create novel pharmaceutical compounds. The introduction of the fluorine atom can alter the molecule's properties, potentially enhancing its efficacy, selectivity, or stability as a drug candidate.
Used in Medical Applications:
Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-4-fluoromay find use in medical applications, where its unique structure and properties can be leveraged for the development of new therapeutic agents or diagnostic tools. Phenylalanine,N-[(1,1-dimethylethoxy)carbonyl]-4-fluoro-'s potential applications in medicine are currently under investigation in pharmaceutical research and development.

Upstream product

• 58632-95-4 2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile 
• 1132-68-9 L-4-fluorophenylalanine 
• 24424-99-5 di-tert-butyl dicarbonate 
• 51-65-0 4-Fluorophenylalanine 
• 1534-90-3 D,L-4-fluorophenylalanine Ethyl Ester Hydrochloride 
• 18125-46-7 (R)-4-fluorophenylalanine 
• 332-30-9 2-amino-3-(4-fluorophenyl)propanoic acid hydrochloride 

Downstream Products

• 186431-68-5 [(S)-1-(4-Fluoro-benzyl)-2-(4-hydroxy-piperidin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester 
• 223526-61-2 ethyl-3->-E-propenoate 
• 1026975-73-4 (E)-(S)-4-[(S)-2-tert-Butoxycarbonylamino-3-(4-fluoro-phenyl)-propionylamino]-5-[(S)-1-(2,4-dimethoxy-benzyl)-2-oxo-piperidin-3-yl]-pent-2-enoic acid ethyl ester 
• 189169-92-4 (Boc-Tyr-D-Ala-Gly-Phe(p-F)-NH-)2 
• 132798-02-8 (4S,7S,10S)-10-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-7-(4-fluoro-benzyl)-3,3-dimethyl-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carboxylic acid 
• 169499-15-4 1,1-dimethylethyl [(1S)-1-[(4-fluorophenyl)methyl]-2-(4-morpholinyl)-2-oxoethyl]carbamate 
• 149267-74-3 (S)-tert-butyl (1-(4-fluorophenyl)-3-hydroxypropan-2-yl)carbamate 
• 1004510-96-6 tert-butoxycarbonyl-4-fluorophenylalanyl ethyl phosphate 
• 1029063-14-6 isopropyl (S)-2-tert-butoxycarbonylamino-3-(4-fluorophenyl)propanoate 
• 1311400-14-2 C₃₆H₄₈F₂N₆O₈ 
• 1311400-16-4 C₄₂H₅₈F₂N₈O₁₀ 
• 1311400-12-0 C₃₂H₄₂F₂N₄O₆ 

Relevant academic research and scientific papers

Design, Synthesis, and Pharmacokinetic Evaluation of Phosphate and Amino Acid Ester Prodrugs for Improving the Oral Bioavailability of the HIV-1 Protease Inhibitor Atazanavir

Phosphate and amino acid prodrugs of the HIV-1 protease inhibitor (PI) atazanavir (1) were prepared and evaluated to address solubility and absorption limitations. While the phosphate prodrug failed to release 1 in rats, the introduction of a methylene spacer facilitated prodrug activation, but parent exposure was lower than that following direct administration of 1. Val amino acid and Val-Val dipeptides imparted low plasma exposure of the parent, although the exposure of the prodrugs was high, reflecting good absorption. Screening of additional amino acids resulted in the identification of an l-Phe ester that offered an improved exposure of 1 and reduced levels of the circulating prodrug. Further molecular editing focusing on the linker design culminated in the discovery of the self-immolative l-Phe-Sar dipeptide derivative 74 that gave four-fold improved AUC and eight-fold higher Ctrough values of 1 compared with oral administration of the drug itself, demonstrating a successful prodrug approach to the oral delivery of 1.

Enantioselective Deaminative Alkylation of Amino Acid Derivatives with Unactivated Olefins

Herein, we report the first Ni-catalyzed enantioselective deaminative alkylation of amino acid and peptide derivatives with unactivated olefins. Key for success was the discovery of a new sterically encumbered bis(oxazoline) ligand backbone, thus offering a de novo technology for accessing enantioenriched sp3-sp3 linkages via sp3 C-N functionalization. Our protocol is distinguished by its broad scope and generality across a wide number of counterparts, even in the context of late-stage functionalization. In addition, an enantioselective deaminative remote hydroalkylation reaction of unactivated internal olefins is within reach, thus providing a useful entry point for forging enantioenriched sp3-sp3 centers at remote sp3 C-H sites.

Structure-Activity Relationships of cyclo(l -Tyrosyl- l -tyrosine) Derivatives Binding to Mycobacterium tuberculosis CYP121: Iodinated Analogues Promote Shift to High-Spin Adduct

A series of analogues of cyclo(l-tyrosyl-l-tyrosine), the substrate of the Mycobacterium tuberculosis enzyme CYP121, have been synthesized and analyzed by UV-vis and electron paramagnetic resonance spectroscopy and by X-ray crystallography. The introduction of iodine substituents onto cyclo(l-tyrosyl-l-tyrosine) results in sub-μM binding affinity for the CYP121 enzyme and a complete shift to the high-spin state of the heme FeIII. The introduction of halogens that are able to interact with heme groups is thus a feasible approach to the development of next-generation, tight binding inhibitors of the CYP121 enzyme, in the search for novel antitubercular compounds.

NOVEL COMPOUNDS WITH DUAL ACTIVITY

The invention generally relate to novel compounds and uses thereof in preventing antifouling by unicellular organisms and in attracting cells from multicellular organisms.

ANTIBACTERIALS AND/OR MODULATORS OF BIOFILM FORMATION AND METHODS OF USING THE SAME

Amides substituted with aromatic groups were synthesized and some were purified to create enantiomer pure compounds. The compounds were tested to determine their ability to inhibit the growth of bacteria and the formation of biofilms created by bacteria. Some of these compounds were found to be effective antibacterials and to effectively inhibit the formation of biofilms.

Dual Catalytic Decarboxylative Allylations of α-Amino Acids and Their Divergent Mechanisms

The room temperature radical decarboxylative allylation of N-protected α-amino acids and esters has been accomplished via a combination of palladium and photoredox catalysis to provide homoallylic amines. Mechanistic investigations revealed that the stability of the α-amino radical, which is formed by decarboxylation, dictates the predominant reaction pathway between competing mechanisms.

Self-assembly of a tripeptide into a functional coating that resists fouling

This communication describes the self-assembly of a tripeptide into a functional coating that resists biofouling. Using this peptide-based coating we were able to prevent protein adsorption and interrupt biofilm formation. This coating can be applied on numerous substrates and therefore can serve in applications related to health care, marine and water treatment.

Solid phase β-lactams synthesis using the Staudinger reaction, monitored by 19F NMR spectroscopy

We report the use of 19F NMR as a simple means to monitor reactions on a solid phase. Multi-step sequences including protection, coupling, deprotection, condensation, cycloaddition and cleavage steps are described in the case of multicomponent reactions involving fluorinated α-aminoesters, aldehydes and acid chlorides.

Antiretroviral hydrazine derivatives

The invention relates to compounds of formula STR1 and salts, pharmaceutical compositions, intermediates and processes of preparation thereof.

Cholecystokinin B antagonists. Synthesis and quantitative structure-activity relationships of a series of C-terminal analogues of CI-988

A study of structure-activity relationships of a series of 'dipeptoid' CCK-B receptor antagonists was performed in which variations of the phenyl ring were examined while the [(2-adamantyloxy)carbonyl]-α-methyl-R)-tryptophan moiety of the potent antagonist CI-988 was kept constant. Since the main focus of this study was phenyl substituent variation, series design techniques were employed to insure an adequate spread of physicochemical properties (lipophilic, steric, electronic), as well as positional substitution. A QSAR analysis on sets of 26 and 16 analogues revealed that CCK-B affinity was related to a combination of the overall size and, marginally, lipophilicity of the phenyl ring substituents (i.e., smaller groups were associated with increased potency with an optimum π near zero, respectively). Further exploration revealed that the dimensions and electronics of the para-phenyl substituent could be related to CCK-B affinity. Increased affinity was seen with short, bulky (branched) electron withdrawing groups. Analogs with small para-substituents appeared to be about 1000-fold CCK-B selective, indicating that selectivity for CCK-B binding is sensitive to phenyl ring substitution. The 4-F-phenyl dipeptoid, derived from this study, has extraordinary high affinity at the CCK-B receptor (IC50 = 0.08 nM) and was also very selective (940-fold CCK-B selective). Consistent with previous reports, (S)-configuration at the substituted phenethylamide center, a carboxylic acid and the presence of a phenyl ring were found to be associated with increased affinity at both CCK-A and CCK-B receptors.