4905-17-3

Upstream product

• 6780-38-7 N-phthaloylglycine chloride 
• 100-46-9 benzylamine 
• 78425-85-1 (N,N-phthaloyl-glycyl)-phosphoric acid dibenzyl ester 
• 2945-03-1 N-benzyl-2-bromoacetamide 
• 1074-82-4 potassium phtalimide 
• 6780-48-9 N-phthaloylglycine anhydride 
• 4702-13-0 N-phthaloylglycine 
• 292067-82-4 N^α-phthaloyl glycine acid fluoroide 
• 33357-94-7 N-Phthaloyl-glycin-p-methoxybenzylester 
• 85-44-9 phthalic anhydride 
• 83539-71-3 N-phthaloylglycine-2-phenyliminooxazolidine 

Downstream Products

• 39796-52-6 N-benzyl-2-aminoacetamide 
• 109564-16-1 N-(1-benzyl-1H-tetrazol-5-ylmethyl)-phthalimide 

Relevant academic research and scientific papers

Radical-Mediated Activation of Esters with a Copper/Selectfluor System: Synthesis of Bulky Amides and Peptides

Herein, we describe a new approach for the activation of esters via a radical-mediated process enabled by a copper/Selectfluor system. A variety of para-methoxybenzyl esters derived from bulky carboxylic acids and amino acids can be easily converted into the corresponding acyl fluorides, directly used in the one-pot synthesis of amides and peptides. As a proof of concept, this method was applied to the iterative formation of sterically hindered amide bonds.

A multigram-scale lower E-factor procedure for MIBA-catalyzed direct amidation and its application to the coupling of alpha and beta aminoacids

The development of direct and atom-economical amidation methods is of high priority because of the importance of amides and peptides as components of pharmaceuticals and commodity chemicals. This article describes the identification of more economical and more practical conditions for direct amidation of carboxylic acids and amines using the MIBA catalyst (5-methoxy-2-iodophenylboronic acid, 6) and its application to the coupling of α- and β-amino acid derivatives. It is now possible to use half of the quantity of molecular sieves prescribed in the original procedure, at a higher concentration leading to a reduction of waste and a substantially improved E-factor. This procedure was validated in the multigram scale preparation of prototypical amides, including aminoacids, using toluene as the solvent. Because of substrate inhibition of the catalyst with monoprotected α-aminoacids, the use of doubly-protected N-phthaloyl α-aminoacids or α-azidoacids is required in order to produce dipeptide products in moderate yields. β-Aminoacids do not suffer from this problem, and Boc-β-aminoacids can be coupled successfully. Unlike other boronic acid catalysts, 6 is active under ambient and low-heat conditions, which helps prevent any epimerization of chiral α-aminoacid derivatives.

Synthesis and screening of cyclooxygenase inhibitory activity of some 1,3-dioxoisoindoline derivatives

In this study, 15 compounds bearing N,Nphthaloylacetamide structure designed by the molecular simplification approach based on thalidomide structure were synthesized and evaluated for inhibitory potencies against cyclooxgenase (COX) isoenzymes, namely COX-1 and COX-2. The results suggested that the N,Nphthaloylacetamide structure, as a primary amide, has inhibitory activity against cyclooxygenase isoenzymes with a higher COX-1 selectivity. The conversion of the primary amide to secondary or tertiary derivatives lowered the potency but favored the COX-2 selectivity thus yielding the compounds with stronger COX-2 inhibiting activity. ECV · Editio Cantor Verlag.

2-AMINO-3,4-DIHYDRO-PYRIDO[3,4-D]PYRIMIDINE DERIVATIVES USEFUL AS INHIBITORS OF BETA-SECRETASE (BACE)

The present invention is directed to 2-amino-3,4-dihydro-pyrido[3,4-d]pyrimidine derivatives of formula (I), pharmaceutical compositions containing them and their use in the treatment of Alzheimer's disease (AD) and related disorders. The compounds of the invention are inhibitors of β-site cleaving enzyme and BACE, BACE1, Asp2 and memapsin2.

NOVEL 2-AMINO-QUINAZOLINE DERIVATIVES USEFUL AS INHIBITORS OF β-SECRETASE (BACE)

The present invention is directed to novel 2-amino-3,4-dihydro-quinazoline derivatives, pharmaceutical compositions containing them and their use in the treatment of Alzheimer’s disease (AD) and related disorders. The compounds of the invention are inhibitors of β-secretase, also known as β-site cleaving enzyme and BACE.

NOVEL 2-AMINO-QUINAZOLINE DERIVATIVES USEFUL AS INHIBITORS OF β-SECRETASE (BACE)

The present invention is directed to novel 2-amino-3, 4-dihydro-quinazoline derivatives, pharmaceutical compositions containing them and their use in the treatment of Alzheimer's disease (AD) and related disorders. The compounds of the invention are inhibitors of P-secretase, also known as n-site cleaving enzyme and BACE.

Synthesis and anticonvulsant activity of N,N-phthaloyl derivatives of central nervous system inhibitory amino acids

In order to study the influence of the length of the amino acid chain of N,N-phthaloyl-amino acid amides as analogues of the former anticonvulsant taltrimide on the seizure-antagonizing activity glycine, β-alanine and γ-aminobutyric acid (GABA) derivatives were synthesized. The corresponding taurine derivatives were also included. Generally, the glycine-derived amides showed a higher activity than the β-alanine and GABA derivatives in the maximal electroshock seizure (MES) test in mice upon intraperitoneal administration. The activity was comparable to the respective taurine derivatives. The N,N-phthaloyl-glycine amides were also active in the MES test upon oral administration to rats. No significant activity was noted in the seizure threshold test with subcutaneous pentylene-tetrazole. The ED50 of N,N-phthaloyl-glycine ethyl amide (4b) in the MES test upon intraperitoneal administration to mice was 19.1 mg/kg. On a molar basis this activity is comparable to the activity of phenytoin with little toxicity in the rotorod test. In conclusion, N,N-phthaloyl-glycine amides might represent promising antiepileptic drugs.

REGENTS AND SYNTHETIC METHODS. 16. AMINOLYSIS OF N-ACYL-2-PHENYLIMINOOXAZOLIDINE. A NEW SYNTHESIS OF AMIDES

N-Acyl-2-phenyliminooxazolidines 7 were easily prepared and treated with several amines at room temperature, yielding amides 9 in very high yields.Possible mechanisms for this transformation are briefly discussed.