50714-59-5

Upstream product

• 54840-09-4 carbamate de methyle et de N(hydroxy-4 phenyle) 
• 106-89-8 epichlorohydrin 
• 118712-54-2 glycidyl p-toluenesulfonate 
• 123-30-8 4-amino-phenol 

Downstream Products

• 52134-41-5 3-[4-(methoxycarbonylamino)phenoxy]-1-isopropylaminopropan-2-ol 
• 33321-66-3 (4-{3-[2-(4-Acetylamino-phenoxy)-ethylamino]-2-hydroxy-propoxy}-phenyl)-carbamic acid methyl ester 
• 102416-95-5 [4-(3-tert-Butylamino-2-hydroxy-propoxy)-phenyl]-carbamic acid methyl ester 

Relevant academic research and scientific papers

Synthesis of methyl-N-[4-(3-R-amino-2-hydroxypropoxy)phenyl]carbamates

By alkylation of methyl-N-(4-hydroxyphenyl)carbamate with (chloromethyl)oxirane in acetone in the presence of K2CO3 methyl-N-[4-(2,3-epoxypropoxy)phenyl]carbamate was prepared. The aminolysis of the latter effected by benzylamine, mo

An integrative study to identify novel scaffolds for sphingosine kinase 1 inhibitors

Sphingosine kinase 1 (SphK1), the enzyme that produces the bioactive sphingolipid metabolite, sphingosine-1-phosphate, is a promising new molecular target for therapeutic intervention in cancer and inflammatory diseases. In view of its importance, the main objective of this work was to find new and more potent inhibitors for this enzyme possessing different structural scaffolds than those of the known inhibitors. Our theoretical and experimental study has allowed us to identify two new structural scaffolds (three new compounds), which could be used as starting structures for the design and then the development of new inhibitors of SphK1. Our study was carried out in different steps: virtual screening, synthesis, bioassays and molecular modelling. From our results, we propose a new dihydrobenzo[b]pyrimido[5,4-f]azepine and two alkyl{3-/4-[1-hydroxy-2-(4-arylpiperazin-1-yl)ethyl]phenyl}carbamates as initial structures for the development of new inhibitors. In addition, our molecular modelling study using QTAIM calculations, allowed us to describe in detail the molecular interactions that stabilize the different Ligand-Receptor complexes. Such analyses indicate that the cationic head of the different compounds must be refined in order to obtain an increase in the binding affinity of these ligands.

Synthesis of potentially β-blocking practolol derivatives: (E + Z)-3- [4-(3-iodoprop-2-enyloxycarbonylamino)phenoxy]-1-(isopropylamino)propan-2-ol

The iodinatied carbamates 3 (E + Z), with potential β-blocking properties, were synthesized. The first route chosen, from 4-aminophenol and the chloroformate 7, had to be abandoned because of the formation of the oxazolidinone 10 during the epoxidation step. The aminoalcohol 17 prepared from the practolol 1 finally gave the target compounds by condensation with the iodoallylic chloroformates 8 (E + Z). The secondary Boc-protected amine function was regenerated without removing the carbamate function situated in the p-postion, by using mild reaction conditions (1 N HCl).

Synthesis and structure-activity relationships of new β-adrenoreceptor antagonists. Evidence for the electrostatic requirements for β-adrenoreceptor antagonists

A series of mono- and disubstituted phenoxypropanolamines, structurally related to practolol and acebutolol, has been synthesized and tested for β-adrenoreceptor blocking activity. Structure-activity relationships are discussed. The reasons for the lack of activity of compounds 3n and 4n have also been examined. The results suggest that the negative electrostatic potential above the phenyl ring of phenoxypropanolamines is essential for binding activity and point to the presence of an electropositive residue in the β-adrenoreceptor binding site.