144902-24-9

Upstream product

• 2935-35-5 (S)-2-phenylglycine 
• 100-46-9 benzylamine 
• 875-74-1 (R)-phenylglycine 
• 17609-52-8 Z-D-phenylglycine 
• 33125-05-2 Boc-D-Phg-OH 
• 147494-90-4 tert-butyl (R)-(2-(benzylamino)-2-oxo-1-phenylethyl)carbamate 
• 81819-47-8 ((R)-Benzylcarbamoyl-phenyl-methyl)-carbamic acid benzyl ester 
• 2835-06-5 phenylglycin 
• 5491-18-9 2-(benzyloxycarbonylamino)-2-phenylacetic acid 
• 1379796-36-7 (RS)-N-benzyl 2-N-(benzyloxycarbonyl)amino-2-phenylacetamide 
• 928314-99-2 (Benzylcarbamoyl-phenyl-methyl)-carbamic acid tert-butyl ester 
• 81917-68-2 2-[(1H-1,2,3-benzotriazole-1-carbonyl)amino]-2-phenylacetic acid 
• 15028-40-7 DL-2-phenylglycine methyl ester hydrochloride 

Downstream Products

• 928314-98-1 rac-N-benzyl-2-benzylamino-2-phenyl-acetamide fumarate 
• 155220-77-2 (R)-N¹-benzyl-1-phenylethane-1,2-diamine 
• 86211-50-9 D,L-Phenylglycin-benzylamid hydrochlorid 

Relevant academic research and scientific papers

Protecting-Group-Free Amidation of Amino Acids using Lewis Acid Catalysts

Amidation of unprotected amino acids has been investigated using a variety of ‘classical“ coupling reagents, stoichiometric or catalytic group(IV) metal salts, and boron Lewis acids. The scope of the reaction was explored through the attempted synthesis of amides derived from twenty natural, and several unnatural, amino acids, as well as a wide selection of primary and secondary amines. The study also examines the synthesis of medicinally relevant compounds, and the scalability of this direct amidation approach. Finally, we provide insight into the chemoselectivity observed in these reactions.

Synthesis, anticonvulsant activity, and neuropathic pain-attenuating activity of N-benzyl 2-amino-2-(hetero)aromatic acetamides

N-Benzyl 2-acetamido-2-substituted acetamides, where the 2-substituent is a (hetero)aromatic moiety, are potent anticonvulsants. We report the synthesis and whole animal pharmacological evaluation of 16 analogues where the terminal 2-acetyl group was removed to give the corresponding primary amino acid derivatives (PAADs). Conversion to the PAAD structure led to a substantial drop in seizure protection in animal tests, demonstrating the importance of the N-acetyl moiety for anticonvulsant activity. However, several of the PAADs displayed notable pain-attenuating activities in a mouse model.

Synthesis of chiral C2-symmetric methylene- and boron-bridged bis(imidazolines)

A series of C2-symmetric boron-bridged bis(imidazolines) was obtained by lithiation of 2-imidazolines and subsequent reaction with dialkyl- or diarylhaloboranes. The corresponding 2-imidazolines were prepared by an efficient four-step sequence starting from N-tert-butoxycarbonyl-protected α-amino acids. C2-Symmetric methylenebis(imidazolines) were readily synthesized from chiral diamines by condensation with diethyl malonimidate. The bis(imidazolines) were used as ligands in the enantioselective cyclopropanation of styrene and allylic oxidation of cyclic alkenes. Georg Thieme Verlag Stuttgart.

ORGANIC COMPOUNDS

The invention relates to novel diamines of the formula (I) in which all variables are as defined in the specification, in free base form or in acid addition salt form, to their preparation, to their use as medicaments and to medicaments comprising them.

The design of phenylglycine containing benzamidine carboxamides as potent and selective inhibitors of factor Xa

Factor Xa. a critical serine protease in the blood coagulation cascade, has become a target for inhibition as a strategy for the invention of novel anti-thrombotic agents. Here we describe the development of phenylglycine containing benzamidine carboxamides as novel, potent and selective inhibitors of factor Xa.

A new route to homochiral piperidines

The synthesis of an enantiomeric pair of enaminoesters from phenylglycine is described. Conjugate addition to α,β-enones, reductive cyclization-fragmentation to octahydroimidazopyridines and further reduction to remove the auxiliary atoms, completes a new route to homochiral piperidines in which the enaminoesters function as homochiral 'ethanal enamines'.

Functionalized DL-Amino Acid Derivatives. Potent New Agents for the Treatment of Epilepsy

Structural analogues of the potent known anticonvulsant agent N-acetyl-DL-alanine N-benzylamide (1a) have been prepared (16 examples).The pharmacological activities of these products were evaluated in the maximal electroshock seizure (MES), the subcutaneous pentylenetetrazole seizure threshold (sc Met), and the rotorod (Tox) tests.The median effective doses (ED50) and the median toxic doses (TD50) for the most active compounds by both intraperitoneal and oral administration are reported.The most active compounds were N-acetyl-DL-phenylglycine N-benzylamide (1d) and N-acetyl-DL-alanine N-m-fluorobenzylamide (1m) along with the parent compound 1a.The ED50 values in the MES test for these three compounds compared well with phenobarbital, while their high TD50 values contributed to their large protective indexes, which approached that of phenytoin.When tested against four convulsant agents, compounds 1a and 1d displayed activity profiles significantly different from those reported for conventionally used antiepileptic drugs.