2382-86-7

Basic information

• Product Name: (R)-N-(2-chloroacetyl)phenylalanine methyl ester
• Synonyms: (R)-N-(2-chloroacetyl)phenylalanine methyl ester
• CAS NO: 2382-86-7
• Molecular Weight: 255.701
• Mol File: 2382-86-7.mol

Chemical Properties

• CAS DataBase Reference: (R)-N-(2-chloroacetyl)phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-N-(2-chloroacetyl)phenylalanine methyl ester(2382-86-7)
• EPA Substance Registry System: (R)-N-(2-chloroacetyl)phenylalanine methyl ester(2382-86-7)

Safety Data

• Hazardous Substances Data: 2382-86-7(Hazardous Substances Data)

Upstream product

• 10065-72-2 L-Alanine methyl ester 
• 79-04-9 chloroacetyl chloride 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 541-88-8 Chloroacetic anhydride 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 79-11-8 chloroacetic acid 
• 63-91-2 L-phenylalanine 

Downstream Products

• 57294-89-0 (3S)-(2-azido-acetylamino)-3-phenyl-propionic acid methyl ester 
• 2382-54-9 N-α-Iodoacetyl-L-phenylalanine methyl ester 
• 169447-84-1 (3S)-1,3-dibenzylpiperazine-2,5-dione 
• 1367887-15-7 C₁₃₆H₁₆₄N₄O₂₀ 
• 204327-96-8 (3S)-1,3-dibenzylpiperazine 
• 1610691-74-1 (R)-N-[N-(2,2-dimethoxyethyl)glycinyl]phenylalanine methyl ester 
• 1610691-77-4 (6R,11bR)-2-cyclohexanecarbonyl-4-oxo-1,3,4,6,7,11b-hexahydro-2H-pyrazino[2,1-a]isoquinoline-6-carboxylic acid 
• 135526-78-2 (-)-Praziquantel 
• 1190439-43-0 (S)-methyll 3-phenyl-(2-(2-phenylselanyl)acetamido)propanoate 
• 466690-04-0 methyl (S)-3-phenyl-2-[2-(phenylthio)acetamido]propanoate 

Relevant articles and documents

Structure-Activity Relationship Studies on Oxazolo[3,4- a]pyrazine Derivatives Leading to the Discovery of a Novel Neuropeptide S Receptor Antagonist with Potent in Vivo Activity

Neuropeptide S modulates important neurobiological functions including locomotion, anxiety, and drug abuse through interaction with its G protein-coupled receptor known as neuropeptide S receptor (NPSR). NPSR antagonists are potentially useful for the treatment of substance abuse disorders against which there is an urgent need for new effective therapeutic approaches. Potent NPSR antagonists in vitro have been discovered which, however, require further optimization of their in vivo pharmacological profile. This work describes a new series of NPSR antagonists of the oxazolo[3,4-a]pyrazine class. The guanidine derivative 16 exhibited nanomolar activity in vitro and 5-fold improved potency in vivo compared to SHA-68, a reference pharmacological tool in this field. Compound 16 can be considered a new tool for research studies on the translational potential of the NPSergic system. An in-depth molecular modeling investigation was also performed to gain new insights into the observed structure-activity relationships and provide an updated model of ligand/NPSR interactions.

One-pot synthesis of 1,2,4-oxadiazoles from chalcogen amino acid derivatives under microwave irradiation

A series of sulfur- and selenium-bearing, amino acid-derived 1,2,4-oxadiazoles were obtained by a simple procedure. The method consists of EDC-promoted coupling of chalcogen amino acid derivatives with arylamidoximes in acetone, followed by solvent removal and microwave irradiation in water medium. Influence of amidoxime substituents, of the chalcogen atom and of the amino acid side chain is discussed. The results showed this to be a fast, easy and effective method to obtain these compounds, with good functional-group tolerance, potentially favouring future applications in organic synthesis.

Design, Synthesis, and In Silico Evaluation of Methyl 2-(2-(5-Bromo/chloro-2-oxobenzoxazol-3(2H)-yl)-acetamido)-3-phenylpropanoate for TSPO Targeting

The high expression of the translocator protein (TSPO) makes it an ideal target for imaging and therapy. The present study is aimed at optimizing acetamidobenzoxazolone-based TSPO ligands by structural modification to overcome the limitations of TSPO ligands of the first two generations such as nonspecificity and polymorphism. Three different TSPO proteins, 2MGY, 4RYQ, and 4UC1, in the native and mutated form were chosen. Acetamidobenzoxazolones modified with phenylalanine methyl ester (methyl 2-(2-(5-bromo/chloro-2-oxobenzooxazol-3(2H)-yl)acetamido)-3-phenylpropanoate, ABPO-Br, ABPO-Cl) through better or comparable docking scores than the known TSPO ligands such as MBMP, FEBMP, FPBMP, and PK11195 are identified as potential TSPO ligands. ABPO-Cl and ABPO-Br were synthesized using phenylalanine methyl ester as a moiety for incorporation of the desired pharmacophoric feature. All the intermediates and final compounds were purified using column chromatography and analytical HPLC (purity > 97%). The purified compounds were characterized by 1H, 13C NMR and mass spectroscopy. Drug likeliness and comparative bioactivity analysis were performed using QikProp through prediction of various properties. Both analogs follow all the five Lipinski rules and three Jogersen’s rules predicting their drug likeliness. The other important aspects related to TSPO ligands such as blood-brain barrier penetration and better contrast have been predicted through lipophilicity (QP log P = 2.76 and 2.74 for ABPO-Br and ABPO-Cl, respectively) and serum binding (QP log Khsa = ?0.18 and ?0.25 for ABPO-Br and ABPO-Cl, respectively). The selectivity and distribution of these TSPO ligands were confirmed by 99mTc-ABPO-Br dynamic image in New Zealand rabbit. These results have shown that the ABPO analogs have the potential to act as better ligands as compared to known acetamidobenzoxazolone derivatives and would be of interest as a promising starting point for designing compounds for TSPO targeting.

Highly efficient enantioselective synthesis of 1,3-disubstituted 2,5-diketopiperazine derivatives via microwave irradiation

Chiral 2,5-diketopiperazine (2,5-DKP) derivatives have a broad range of biological activities in the medicinal field. The synthetic protocols of 1,3-disubstituted 2,5-DKPs via base-catalyzed cyclization of chloroacetamide have been reported. However, there are several drawbacks, such as an overly long reaction time, low to moderate yield, and racemization of the products. The sequence modified herein of 1,3-disubstituted 2,5-DKPs involves microwave-assisted cyclization. It increases yields and reduces reaction time. Furthermore, employing N-PMB protection prevents racemization, which frequently occurs in the base-catalyzed cyclization reaction. Consequently, the rapid synthetic method of enantiomerically pure 1,3-disubstituted 2,5-DKPs via microwave reaction was established successfully.

Enantiomerically pure piperazines via NaBH4/I2reduction of cyclic amides

Enantiomerically pure (3S,7R,8aS)-3-phenyloctahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-methyl octahydropyrrolo[1,2-a]pyrazine-7-ol, (3S,7R,8aS)-3-isopropyloctahydropyrrolo[1,2-a]pyrazine-7-ol and (3S,7R,8aS)-3-isobutyloctahydropyrrolo[1,2-a]pyrazine-7-ol 16d were synthesized via preparation of the corresponding cyclic amides from enantiomerically pure L-proline and hydroxyproline derivatives followed by reduction using sodium borohydride-iodine.

Diastereoselective synthesis of novel 5-substituted morpholine-3-phosphonic acids: Further exploitation of N-acyliminium intermediates

The first diastereoselective total synthesis of 5-substituted morpholine-3-phosphonic acids is reported. The principal feature of the synthesis is the introduction of a dimethyl phosphonate group into 5-substituted morpholin-3-ones. The procedure is based

Efficient method for the synthesis of α-amidophosphonates via the michaelis-arbuzov reaction

A new series of modified β-amidophosphonates (or β- ketophosphonate) was synthesized by an efficient method, starting from aminoesters and chloroacetyl chloride. We have established that chloroacetyl chloride is a suitable reagent allowing the introduction a halogen moiety for the Arbuzov reaction. The α-amidophosphonates were prepared in two steps (acetylation, phosphorylation). Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file. Copyright

Synthesis of L-phenylalanine ester derivatives of p-tert-butylcalix[8]arene

Synthetic routes were developed to link L-phenylalanine ester at the lower rim of p-tert-butylcalix[8]arene. Amide-type halides (2a-c) were synthesized by chloroacetic chloride and L-phenylalanine ester hydrochloride (1a-c), then reacted with p-tert-butyl

Click chemistry inspired synthesis of novel ferrocenyl-substituted amino acids or peptides

This work reports on the synthesis of a wide range of ferro- cenyl-substituted amino acids and peptides in excellent yield. Conjugation is established via copper-catalyzed 1,3- dipolar cycloaddition. Two complementary strategies were employed for conjugation, one involving cycloaddition of amino acid derived azides with ethynyl ferrocene 1 and the other involves cycloaddition between amino acid derived al- kynes with ferrocene-derived azides 2 and 3. Labeling of amino acids at multiple sites with ferrocene is discussed. A new route to 1,1'-unsymmetrically substituted ferrocene conjugates is reported. A novel ferrocenophane 19 is accessed via bimolecular condensation of amino acid derived bis- alkyne 9b with the azide 2. The electrochemical behavior of some selected ferrocene conjugates has been studied by cyclic voltammetry.

Synthesis and structure of 1,4-dipiperazino benzenes: Chiral terphenyl-type peptide helix mimetics

(Chemical Equation Presented) The terphenyl structure has been proven to be an ideal scaffold mimicking side-chain functionalities of peptidic α-helices. The synthesis of 1,4-dipiperazino benzenes, using stepwise transition metal-catalyzed N-arylation of chiral piperazines to a central benzene core is reported. The structure determination by X-ray crystallography reveals a geometrical arrangement of the hydrophobic side chains resembling the orientation of key i, i + 3, and i + 7 positions in a peptidic α-helix or in terphenyl helix mimetics.