54840-09-4

Upstream product

• 2603-10-3 N-phenyl methyl carbamate 
• 67-56-1 methanol 
• 100-02-7 4-nitro-phenol 
• 201230-82-2 carbon monoxide 
• 51-78-5 p-aminophenol hydrochloride 
• 79-22-1 methyl chloroformate 
• 123-30-8 4-amino-phenol 

Downstream Products

• 50714-59-5 3-[4-(methoxycarbonylamino)phenoxy]-1,2-epoxypropane 
• 54840-16-3 methyl N-(4-hydroxy-3-nitrophenyl)carbamate 
• 444348-42-9 methyl p-(4-bromobutoxy)phenylcarbamate 
• 54840-22-1 methyl p-allyloxyphenylcarbamate 
• 52134-41-5 3-[4-(methoxycarbonylamino)phenoxy]-1-isopropylaminopropan-2-ol 
• 123-30-8 4-amino-phenol 
• 102416-95-5 [4-(3-tert-Butylamino-2-hydroxy-propoxy)-phenyl]-carbamic acid methyl ester 

Relevant academic research and scientific papers

SSAO INHIBITORS AND USES THEREOF

Described herein are compounds that are semicarbazide-sensitive amine oxidase (SSAO) inhibitors, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds in treating or preventing a liver disease or condition.

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 methyl p-alkoxyphenylcarbamates and some their reactions

Alkylation of methyl p-hydroxyphenylcarbamate with allyl bromide and 1,4-dibromobutane leads to formation of the corresponding methyl p-alkoxyphenylcarbamates. Reactions of methyl p-allyloxyphenyl-carbamate with benzaldehyde, p-methoxybenzaldehyde, p-nitr

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 of functionalized carbamates through a palladium-catalyzed reductive carbonylation of substituted nitrobenzenes

The palladium-catalyzed reductive carbonylation of ortho and para-substituted nitrobenzenes has proven to be an attractive route for the synthesis of functionalized carbamates. For the Pd(1,10-phenanthroline)2(triilate}2 catalyst system, the scope of the reaction has been studied. Substrates with electron-donating substituents at the para position were found to decrease the catalytic activity, most probably as a result of their relatively low oxidizing capacity. The selectivity towards the desired carbamate, however, was increased for these substrates. Under the influence of electron-withdrawing substituents the azoxybenzene and azobenzene derivatives became important side products. Introduction of large steric hindrance at the ortho position of the nitro substrates gave rise to an interesting side reaction, viz. methoxylation of the aromatic ring. The methoxylation reaction appeared to occur on an intermediate species in the catalytic cycle. Several functionalities have shown to be resistant to the reaction conditions required for the conversion of the nitro group. Especially with 4-nitrobenzoic acid, an extremely high activity and selectivity was found, thus yielding a very convenient synthesis for N-protected amines containing carboxylic acid functions. VCH Verlagsgesellschaft mbH.

CARBONYLATIVE REDUCTION OF NITROPHENOLS TO AMINOPHENOLS

Two- or three-component catalysts composed of (i) sulfur or sulfur compound (H2S, CS2, COS, Na2S), (ii) basic additive (triethylamine, CH3ONa, Na2S), and usually (iii) vanadium(V) compounds (e.g.NH4VO3) were found to catalyze efficiently the reaction of CO + H2O with isomeric nitrophenols to give the corresponding aminophenols.The reaction proceeds smoothly at 398 and 483 K and initial pressure of 7 MPa, and its rate increases from 2- to 4-nitrophenol.The selectivity to aminophenols exceeding 96 per cent was obtained at the water to nitrophenol molar ratio higher than 5.The solvents such as methanol and dioxane ensured better contact of the reactants, which was necessary for achievement of such a high selectivity.The effectiveness of the sulfur components (based on the S content) is expressed by the following sequence: S : CS2 : Na2S : H2S : COS = 1 : 1.2 : 2.5 : 10 : 11.The reaction takes place also under the reduced CO pressure to 0.1 - 0.35 MPa.Formation of side products and mechanism of the reaction are discussed.

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.

HYDROXYLATION DIRECTE D'ESTERS DE PHENYLE ET D'ANILIDES PAR LE PEROXYDE D'HYDROGENE EN MILIEU SUPERACIDE

In SbF5-HF, hydrogen peroxide reacts on the aromatic ring of esters 1a-5a and anilides 11a-15a to give monohydroxylated derivatives in good yields.With compounds 2a, 4a and 5a, meta or para isomers are by far the major products, whereas with formate 1a and benzoate 3a, the proportion of the ortho isomer is more important.With anilides, the reaction is less selective, the three isomers being obtained in comparable amounts.Thus, the relative proportions of ortho, meta and para-hydroxylated derivatives obtained using 70 percent H2O2 with acetate 2a and acetanilide 12a are 6/51/43 and 36.5/30/33.5, respectively.The important proportion of meta hydroxylation is the result of the reaction of protonated hydrogen peroxide H3O2+ on the protonated substrate.

Ester of (alkynyloxy)-, (alkenyloxy)-, and (cyanoalkoxy) carbanilic acids and their use as herbicides

The invention is novel esters of (alkynyloxy)-, (alkenyloxy)-, and (cyanoalkoxy) carbanilic acids and the thiono and dithio derivatives of the carbanilic acids, and their use for controlling broadleaf weeds and grasses.