38465-16-6

Usage

Uses

Used in Pharmaceutical Industry:
2-GLYCIDYLOXYBENZONITRILE is used as a synthetic intermediate for the development of novel (aryloxy)propanolamines and their derivatives. These compounds exhibit antarrhythmic and beta-blocking effects, making them valuable in the treatment of various cardiovascular conditions such as arrhythmias, hypertension, and angina.
In the synthesis of these pharmaceutical compounds, 2-GLYCIDYLOXYBENZONITRILE serves as a key component due to its reactive epoxide and nitrile groups, which can be further functionalized to create a diverse range of bioactive molecules with potential therapeutic applications.
Additionally, the compound may also find applications in other industries, such as the chemical or materials science fields, where its unique structural features can be exploited for the development of new materials or chemical processes.

InChI:InChI=1/C10H9NO2/c11-5-8-3-1-2-4-10(8)13-7-9-6-12-9/h1-4,9H,6-7H2

Upstream product

• 611-20-1 salicylonitrile 
• 3132-64-7 1,2-Epoxy-3-bromopropane 
• 106-89-8 epichlorohydrin 
• 115314-14-2 (R)-glycidyl nosylate 
• 110-89-4 piperidine 
• 42864-99-3 (RS)-1-chloro-3-(2-cyanophenoxy)propan-2-ol 

Downstream Products

• 53671-21-9 1-(2-cyanophenoxy)-3-β-propionamidoethylamino-2-propanol 
• 83019-64-1 {2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-urea 
• 53855-93-9 N-{2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-isobutyramide 
• 53671-74-2 1-Butyl-3-{2-[3-(2-cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-urea 
• 53671-80-0 N-{2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-propyl}-2-phenyl-acetamide 
• 53671-56-0 2-(2-Chloro-phenyl)-N-{2-[3-(2-cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-acetamide 
• 53672-24-5 N-{2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-2,2-dimethyl-propionamide 
• 53671-40-2 N-{2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-benzenesulfonamide 
• 53671-71-9 1-(2-cyanophenoxy)-3-β-(3-phenylureido)ethylamino-2-propanol 
• 83019-60-7 1-(4-Chloro-phenyl)-3-{2-[3-(2-cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-urea 
• 83019-65-2 3-<<2-(3-methylureido)ethyl>amino>-1-(2-cyanophenoxy)propan-2-ol 
• 83019-59-4 1-(2-Chloro-phenyl)-3-{2-[3-(2-cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-urea 
• 83019-58-3 1-{2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-3-(2-methoxy-phenyl)-urea 
• 83019-61-8 1-{2-[3-(2-Cyano-phenoxy)-2-hydroxy-propylamino]-ethyl}-3-(2-nitro-phenyl)-urea 

Relevant academic research and scientific papers

Chelation-directed remote: Meta -C-H functionalization of aromatic aldehydes and ketones

We disclose herein the development of a versatile 1,2-diol directing template for palladium-catalyzed remote meta-C-H functionalization of aromatic aldehydes and ketones. In situ-generation of acetals and ketals, as well as removal afterwards, makes the C-H bond functionalization process more straightforward and efficient. This also represents the first example of chelation-directed meta-C-H functionalization of aromatic aldehydes and ketones.

Synthesis of 2-(phenoxymethyl)oxirane derivatives through unexpected rearrangement of oxiran-2-ylmethyl benzenesulfonates

The synthesis of 2-(phenoxymethyl)oxirane derivatives from oxiran-2-ylmethyl benzenesulfonates was developed through a base promoted rearrangement. A new C-O bond was formed along with the unexpected cleavage of C-S bond via this process. This unusual reaction was characterized with mild reaction conditions, high efficiency, and excellent functional group tolerance. A plausible reaction mechanism was proposed on the basis of experimental results and control experiments.

Efficient chemoenzymatic synthesis of (RS)-, (R)-, and (S)-bunitrolol

A new chemical and the first chemoenzymatic synthesis of β-adrenergic receptor blocking agent bunitrolol is reported in racemic (RS) and enantioenriched forms (R and S). The intermediates (R)- and (S)-1-chloro-3-(2- cyanophenoxy)propan-2-ol intermediates were synthesized from the corresponding racemic alcohol through enzymatic kinetic resolution. The commercial available lipases PS-C and CCL exhibited complementary enantioselectivity during transesterification of the racemic alcohol with vinyl acetate affording the (R)-alcohol along with (S)-acetate and the (S)-alcohol along with (R)-acetate, respectively, and represent an example of enzymatic switch for reversal of enantioselectivity. The effects of various reaction parameters, such as temperature, time, substrate and enzyme concentration, and reaction medium, on the activity and enantioselectivity were optimized. The (R)- and (S)-alcohols were converted into (S)-and and (R)-bunitrolol, respectively, by treatment with tert-butylamine. The (R)- and (S)-acetates, obtained enzymatically were deacetylated to the corresponding alcohol by chemical hydrolysis and further converted into (S)-and and (R)-bunitrolol by chemical means. This is the first chemoenzymatic synthesis of both of the enantiomers of the drug. (RS)-, (R)-, and (S)-Bunitrolol were also synthesized following the 'all chemical' routes from (RS)-, (R)-, and (S)-epichlorohydrin via the corresponding (RS)-, (S)-, and (R)-2-cyanoglycidyl ether and the (RS)-, (R)-, and (S)-1-chloro-3-(2- cyanophenoxy)propan-2-ol intermediates with improved overall yields and better enantiomeric excesses compared to the reported processes.

A smart library of epoxide hydrolase variants and the top hits for synthesis of (S)-β-blocker precursors

Microtuning of the enzyme active pocket has led to a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots. This study represents a breakthrough in protein engineering of epoxide hydrolases and resulted in enhanced activity toward bulky substrates. Hot pockets: Microtuning of the enzyme active pocket gives a smart library of epoxide hydrolase variants with an expanded substrate spectrum covering a series of typical β-blocker precursors. Improved activities of 6- to 430-fold were achieved by redesigning the active site at two predicted hot spots, and enhanced activity toward bulky substrates was found.

Improvement and simplification of synthesis of 3-aryloxy-1,2-epoxypropanes using solvent-free conditions and microwave irradiations. Relation with medium effects and reaction mechanism

Some 3-aryloxy-1,2-epoxypropanes, interesting as potential synthons in β-adrenergic receptor antagonists preparation, were obtained in excellent yields (65-96% within 2-17 min) by microwave activation (monomode system) using solid-liquid solvent-free phase transfer catalysis (PTC). The best results for the O-alkylation of some phenols with epichlorohydrin were obtained using TBAB and NaOH/K2CO3 (1:4 mol/mol) as phase transfer catalyst and more acceptable basic system, respectively. These new procedure is compared with classical methods. Significant specific microwave effect (non-purely thermal) was evidenced in all cases. They were discussed in terms of reaction medium and mechanism, taking into account the variations in polarity of the systems.

Design of new beta1-selective adrenoceptor ligands as potential radioligands for in vivo imaging.

In general, the failing human heart is characterized by a selective reduction in beta(1)-adrenoceptors (beta(1)-ARs) without change in beta(2)-AR density. Medical imaging techniques, either single photon emission computed tomography (SPECT) or positron emission tomography (PET) with appropriate radioligands, offer the possibility of assessing beta-adrenoceptor density non-invasively in humans. To date, neither a SPECT nor a PET radioligand is available for the selective imaging of cardiac beta(1)-ARs. The aim of this study was to develop potential high affinity beta(1)-selective AR radioligands for the non-invasive in vivo imaging of the beta(1)-AR density in the human heart using SPECT or PET. A variety of racemic N-aryl-N'-[2-[3-aryloxy-2-hydroxy-propylamino]-ethyl]-urea derivatives and chain-elongated analogues, related to the established beta(1)-AR antagonist, ICI 89,406 8i, were synthesized. Competition studies using the non-selective AR ligand, [(125)I]iodocyanopindolol ([(125)I]ICYP), and ventricular membrane preparations of wild-type mice revealed nine ligands with higher beta(1)-AR affinities (up to 76-fold) and beta(1)-AR selectivities (up to 139-fold) than 8i. Mostly, these ligands possess a 2-substituted phenoxy group and a 4-substituted phenyl residue in contrast to the lead compound 8i. The non-radioactive counterparts of the desired SPECT- and PET-radiotracers were synthesized as reference compounds [e.g., 8f, 8g, 8h and 8l as the non-radioactive analogues of the radioiodinated SPECT radioligands, 8e and 8h as the non-radioactive compounds of C-11 labelled PET-tracers (C-11 in the methoxy group)]. The established library of high affinity beta(1)-selective AR antagonists was screened for chemical precursors for the radiosynthesis of the mentioned radioligands. Furthermore, the library consists of some comparison compounds that are unsubstituted, allyl- and alkyl-substituted or chain-elongated (e.g., 8a, 8j, 8o and 8r-t). Future steps will include radiolabelling and pharmacokinetic evaluation of the beta(1)-selective target compounds, which could be applied as sympathetic innervation agents for in vivo investigations and diagnostics in patients suffering from cardiac diseases like heart failure and ventricular arrhythmias.

Method of using calcilytic compounds

The present invention features calcilytic compounds. "Calcilytic compounds" refer to compounds able to inhibit calcium receptor activity. Also described are the use of calcilytic compounds to inhibit calcium receptor activity and/or achieve a beneficial effect in a patient; and techniques which can be used to obtain additional calcilytic compounds.

1-ARYLOXY-3-(SUBSTITUTED ALKYLAMINO)-2-PROPANOLS AND USE AS BETA-BLOCKER

1-Aryloxy-3-(substituted alkylamino)-2-propanols having the general information: STR1 and their pharmaceutically acceptable salts exhibit cardioselective β-adrenergic blocking activity, and are useful as antihypertensive, cardioprotective, antiarrhythmic

1-ARYLOXY-3-(SUBSTITUTED ALKYLAMINO)-2-PROPANOLS, PHARMACEUTICAL COMPOSITIONS AND USE

The 1-aryloxy-3-(substituted alkylamino)-2-propanols of this invention and their pharmaceutically acceptable salts exhibit cardioselective β-adrenergic blocking activity, and are useful as antihypertensive, cardioprotective, antiarrhythmic and, antiangina