536-21-0

Usage

InChI:InChI=1S/C8H11NO2/c9-5-8(11)6-2-1-3-7(10)4-6/h1-4,8,10-11H,5,9H2

Upstream product

• 90005-54-2 2-amino-1-(3-hydroxyphenyl)ethyl ketone 
• 857561-03-6 2-azido-1-(3-benzoyloxy-phenyl)-ethanone 
• 2491-37-4 2-bromo-1-(3-hydroxyphenyl)ethanone 
• 53313-95-4 α,3-dihydroxybenzeneacetonitrile 
• 620-18-8 3-hydroxystyrene 
• 1415155-47-3 3-(non-8-enyl)phenol 
• 139-27-5 3-benzoyloxy-ω-bromoacetophenone 
• 100-83-4 meta-hydroxybenzaldehyde 
• 852159-27-4 1-(3-hydroxyphenyl)-2-nitro-ethanol 

Downstream Products

• 1420-80-0 (-)-Norphenylephrine 
• 5596-07-6 (+)-Norphenylephrine 
• 25283-28-7 2-benzylidenamino-1-(3-hydroxy-phenyl)-ethanol 
• 3571-71-9 m-hydroxy-α-[(isopropylamino)methyl]benzyl alcohol 
• 57614-96-7 3-(2-phenyl-oxazolidin-5-yl)-phenol 
• 57614-98-9 3-[2-(3,4-dimethoxy-phenyl)-oxazolidin-5-yl]-phenol 
• 57614-97-8 3-[2-(3-methoxy-phenyl)-oxazolidin-5-yl]-phenol 
• 57614-95-6 5-(3-Hydroxyphenyl)-2,2-dimethyloxazolidine 
• 77745-52-9 2,2,3,3,3-Pentafluoro-propionic acid 2-(2,2,3,3,3-pentafluoro-propionylamino)-1-[3-(2,2,3,3,3-pentafluoro-propionyloxy)-phenyl]-ethyl ester 
• 3458-98-8 3-hydroxyphenylethylamine hydrochloride 
• 110193-51-6 2-ethyl-4,5-dihydro-5-(3-hydroxyphenyl)-1,3-oxazole 
• 831171-98-3 N-[2-hydroxy-2-(3-hydroxy-phenyl)-ethyl]-butyramide 
• 110205-31-7 2-Ethyl-4,5-dihydro-5-[3-[(2-quinolinyl)methoxy]phenyl]-1,3-oxazole 
• 110193-45-8 5-[3-(2-quinolinylmethoxy)phenyl]-2-oxazolidinone 

Relevant academic research and scientific papers

Synthesis of pharmaceutical drugs from cardanol derived from cashew nut shell liquid

Cardanol from cashew nut shell liquid extracted from cashew nut shells was successfully converted into various useful pharmaceutical drugs, such as norfenefrine, rac-phenylephrine, etilefrine and fenoprofene. 3-Vinylphenol, the key intermediate for the synthesis of these drugs, was synthesised from cardanol by ethenolysis to 3-non-8-enylphenol followed by isomerising ethenolysis. The metathesis reaction worked very well using DCM, but the greener solvent, 2-methyl tetrahydrofuran, also gave very similar results. Hydroxyamination of 3-vinylphenol with an iron porphyrin catalyst afforded norfenefrine in over 70% yield. Methylation and ethylation of norfenefrine afforded rac-phenylephrine and etilefrine respectively. A sequence of C-O coupling, isomerising metathesis and selective methoxycarbonylation afforded fenoprofene in good yield. A comparison of the routes described in this paper with some standard literature syntheses of 3-vinylphenol and of the drug molecules shows significant environmental advantages in terms of precursors, yields, number of steps, conditions and the use of catalysts. The Atom Economy of our processes is generally similar or significantly superior to those of the literature processes mainly because the side products produced during synthesis of 3-vinylphenol (1-octeme, 1,4-cyclohexadiene and propene) are easily separable and of commercial value, especially as they are bio-derived. The E Factor for the production of 2-vinylphenol by our process is also very low compared with those of previously reported syntheses.

Novel amide- and sulfonamide-based aromatic ethanolamines: Effects of various substituents on the inhibition of acid and neutral ceramidases

In the present study we describe the design and synthesis of a series of amide- and sulfonamide-based compounds as inhibitor of recombinant acid and neutral ceramidases. Inhibition of ceramidases has been shown to induce apoptosis and to increase the efficacy of conventional chemotherapy in several cancer models. B-13, lead in vitro inhibitor of acid ceramidase has been recently shown to be virtually inactive towards lysosomal acid ceramidase in living cells at lower concentrations and for a shorter time of treatment, suggesting the development of more potent inhibitors. In this study, a detailed SAR investigation has been performed to understand the effect of different substituents on the phenyl ring of amide- and sulfonamide-based compounds that partially resemble the structure of well-known inhibitors such as B-13, D-e-MAPP as well as NOE. Our results suggest that the electronic effects of the substituents on phenyl ring in B-13 and D-e-MAPP analogues have negligible effects either in enhancing the inhibition potencies or for selectivity towards aCDase over nCDase. However, the hydrophobicity and the steric effects of longer alkyl chains (n-Pr, n-Bu or t-Bu groups) at the phenyl ring were found to be important for an enhanced selectivity towards aCDase over nCDase.

Novel 1H-(benzimidazol-2-yl)-1H-pyridin-2-one inhibitors of insulin-like growth factor I (IGF-1R) kinase

A novel class of 1H-(benzimidazol-2-yl)-1H-pyridin-2-one inhibitors of insulin-like growth factor I (IGF-1R) kinase is described. This report discusses the SAR of 4-(2-hydroxy-2-phenylethylamino)-substituted pyridones with improved IGF-1R potency.

Synthesis of [11C](-)-α,α-dideutero-phenylephrine for in vivo kinetic isotope studies

(-)-[11C]Phenylephrine and positron emission tomography could potentially be used to assess neuronal monoamine oxidase activity in the heart. Previous data for (-)-[11C]phenylephrine indicated that, although its retention and neuronal selectivity parallel that of the neuronal mapping agent (-)-[11C]hydroxyephedrine, its neuronal storage and clearance properties are quite different. In order to study the in vivo kinetics of (-)-[11C]phenylephrine in greater detail, the dideutero analog [11C]-(-)-α,α-dideutero-phenylephrine, was synthesized by [11C]methylation of the precursor (-)-α,α-dideutero-m-octopamine. The key step in the procedure was BD3 reduction of the cyanohydrin derived from 3-hydroxybenzaldehyde. Deuterium incorporation at the alpha positions of m-octopamine was confirmed by NMR and mass spectroscopy of the deuterated product and by comparison of spectral data with undeuterated m-octopamin, (-)-α,α-Dideutero-m-octopamine was methylated with CF3SO311CH3 to give suitable for animal and clinical studies.

Pharmaceutical formula

The present invention concerns a pharmacological vehicle or carrier system, which makes possible administration of the active ingredient with a high absorption thereof in the blood circulation of the patient treated therewith, in particular also in the case of oral administration. The pharmacological vehicle system according to the invention comprises ultrafine particles of a reaction product of a reactive derivative of an at least dibasic inorganic acid or an alkane-carboxylic acid having 2 or 3 carboxyl groups and optionally one or two hydroxy groups, wherein one bond of the dibasic inorganic acid or one carboxy group of the alkane-carboxylic acid is bonded to a pharmacological active ingredient containing a hydroxy group, SH group and/or a primary or secondary amino group having a ractive hydrogen atom on this group, and the other bond is bonded to the free hydroxy group of a glycerolipid having at least one free hydroxy group on the glycerol. The invention further concerns these reaction products and a process for the preparation of ultrafine particles of these reaction products.