28150-30-3

Usage

Uses

Used in Pharmaceutical Industry:
[[P-(Benzyloxy)phenoxy]methyl]oxirane is used as a reagent for the preparation of adrenergic agents, which are crucial in the treatment of various medical conditions. These agents include beta-adrenergic blocking agents, β1-adrenoceptor ligands, and β-adrenergic agonists. [[p-(benzyloxy)phenoxy]methyl]oxirane plays a vital role in the development of these drugs due to its ability to facilitate the synthesis process and improve the overall effectiveness of the final products.
In the synthesis of beta-adrenergic blocking agents, [[p-(benzyloxy)phenoxy]methyl]oxirane is used to create compounds that can effectively block the action of adrenaline and noradrenaline, thus helping to lower blood pressure and reduce the workload on the heart. This application is particularly useful in the treatment of hypertension, angina, and certain arrhythmias.
As a reagent for the preparation of β1-adrenoceptor ligands, [[p-(benzyloxy)phenoxy]methyl]oxirane contributes to the development of drugs that selectively target the β1-adrenergic receptors. These ligands are essential in the treatment of conditions such as chronic obstructive pulmonary disease (COPD) and heart failure, where selective targeting of β1-receptors can provide more precise and effective therapy.
In the synthesis of β-adrenergic agonists, [[p-(benzyloxy)phenoxy]methyl]oxirane is used to create compounds that can stimulate the adrenergic receptors, leading to an increase in heart rate, blood pressure, and bronchodilation. These agonists are commonly used in the treatment of asthma, chronic obstructive pulmonary disease (COPD), and certain cardiovascular conditions.
Overall, [[p-(benzyloxy)phenoxy]methyl]oxirane plays a significant role in the pharmaceutical industry, particularly in the development and synthesis of adrenergic agents that are essential for the treatment of various medical conditions. Its unique chemical properties and reactivity make it a valuable compound in the ongoing research and development of new and improved drugs.

InChI:InChI=1/C16H16O3/c1-2-4-13(5-3-1)10-17-14-6-8-15(9-7-14)18-11-16-12-19-16/h1-9,16H,10-12H2

Upstream product

• 103-16-2 4-Benzyloxyphenol 
• 106-89-8 epichlorohydrin 
• 3132-64-7 1,2-Epoxy-3-bromopropane 

Downstream Products

• 53671-92-4 N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-propionamide 
• 53672-46-1 N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-isobutyramide 
• 53671-98-0 N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-2-phenyl-acetamide 
• 53672-07-4 N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-methanesulfonamide 
• 53671-94-6 N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-2-methoxy-acetamide 
• 53672-82-5 1-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-propyl}-3-phenyl-urea 
• 53672-03-0 N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-benzenesulfonamide 
• 70636-53-2 1-<2-<<2-hydroxy-3-(4-hydroxyphenoxy)propyl>amino>ethyl>-3-phenylurea 
• 53671-96-8 N-{2-[2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-ethyl}-benzamide 
• 34380-47-7 (+/-)-1-[p-(benzyloxy)phenoxy]-3-(isopropylamino)propan-2-ol 
• 1026616-93-2 4-[3-(4-benzyloxy-phenoxy)-2-hydroxy-propoxy]-benzoic acid allyl ester 
• 1263187-16-1 2-{[4-(benzyloxy)phenoxy]methyl}-6-nitro-2,3-dihydroimidazo[2,1-b][1,3]oxazole 

Relevant academic research and scientific papers

6-Nitro-2,3-dihydroimidazo[2,1-b][1,3]thiazoles: Facile synthesis and comparative appraisal against tuberculosis and neglected tropical diseases

As part of a quest for backups to the antitubercular drug pretomanid (PA-824), we investigated the unexplored 6-nitro-2,3-dihydroimidazo[2,1-b][1,3]-thiazoles and related -oxazoles. The nitroimidazothiazoles were prepared in high yield from 2-bromo-4-nitroimidazole via heating with substituted thiiranes and diisopropylethylamine. Equivalent examples of these two structural classes provided broadly comparable MICs, with 2-methyl substitution and extended aryloxymethyl side chains preferred; albeit, S-oxidised thiazoles were ineffective for tuberculosis. Favourable microsomal stability data for a biaryl thiazole (45) led to its assessment in an acute Mycobacterium tuberculosis mouse model, alongside the corresponding oxazole (48), but the latter proved to be more efficacious. In vitro screening against kinetoplastid diseases revealed that nitroimidazothiazoles were inactive versus leishmaniasis but showed interesting activity, superior to that of the nitroimidazooxazoles, against Chagas disease. Overall, “thio-delamanid” (49) is regarded as the best lead.

A new synthesis of sultams from amino alcohols

The base-mediated cyclization of N,O-dimesylate derivatives of cyclic and acyclic amino alcohols provides a simple access to five- and six-member sultams: isothiazolidine-1,1-dioxides and thiazinane-1,1-dioxides respectively.

NITROIMIDAZOOXAZINE AND NITROIMIDAZOOXAZOLE ANALOGUES AND THEIR USES

The current invention pertains to nitroimidazooxazine and nitroimidazooxazole analogues, their methods of preparation, and uses of the compounds as treatment for Mycobacterium tuberculosis, for use as anti-tubercular drugs, for use as anti-protozoal agents with unexpectedly high potency against Trypanosoma cruzi or Leishmania donovani, and for the treatment of other microbial infections.

A vHTS approach for the identification of β-adrenoceptor ligands

Using a vHTS based on a pharmacophore alignment on known β3-adrenoceptor ligands, a set of intriguing β-adrenoceptor ligands was identified, optimization of which resulted in a selective and potent human β2-AR antagonist.

LTA4H modulators and uses thereof

Leukotriene A4 hydrolase (LTA4H) inhibitors, compositions containing them, and methods of use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation.

BENZIMIDAZOLE, BENZTHIAZOLE AND BENZOXAZOLE DERIVATIVES AND THEIR USE AS LTA4H MODULATORS

Leukotriene A4 hydrolase (LTA4H) inhibitors of formula I, compositions containing them, and their use for the inhibition of LTA4H enzyme activity and the treatment, prevention or inhibition of inflammation and/or conditions associated with inflammation, wherein X is selected from the group consisting of NR5, O, and S, with R5 being one of the H and CH3; Y is selected from the group consisting of CH2 and O; R4 is selected from the group consisting of H, OCH3, Cl, F, Br, I, OH, NH2, CN, CF3.

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.

Phenyl-pyridinium salts and use thereof in inhibiting intestinal resorption

Polycyclic salts of the formula wherein A- is the anion of a strong organic or inorganic acid; XN+ is pyridinium, pyrimidinium, thiazolium or imidazolium substituted by R1, R2 and R3 ; n, q and r individually are the integer 1 or 0 and p is an integer from 1 to 15; Y is CH2, C(H,OH) or C(O): Z is O, S, CH2, C(O), NQ1, SO2, C(O)O, OC(O), C(O)N(Q1) or N(Q1)C(O); L is p-phenylene substituted by R4 ; and M is phenyl substituted by R5 and R6, T has one of the meanings given above, for Z or is C(CH3)2, C2 H4, C(Q2)=C(Q3), C C, CH2 C(O), C(O)CH2, CH2 O or OCH2, R1 is a group Ar, Ar-C1-4 -alkyl, ArO or ArC(O), Ar is phenyl substituted by R7, R8 and R9 ; R2 and R3 individually are H, C1-4 -alkyl, C1-4 -alkoxy or C6 H5, with the proviso that the N-atom in the 3-position of an imidazolium group XN+ is substituted by Ar, Ar-C1-4 -alkyl or C1-4 -alkyl, R4, R5, R6, R7, R8 and R9 individually are H, halogen, CF3, NO2, CN, C1-4 - -(alkyl, alkoxy, alkylthio or alkylsulphonyl), SO2 N(R,Q), C(O)N(Q4,Q5), C(O)Q4, C(O)OQ4 or OC(O)Q4, R, Q, Q1, Q2 and Q3 individually are H or C1-4 -alkyl, and Q4 and Q5 individually are C1-4 -alkyl inhibit the intestinal resorption of cholesterol and of bile salts in the enterohepatic circulation. These salts containing a quaternary N-atom can be manufactured starting from corresponding amines.

(S)-1-[2-(4-HYDROXY-S-(1-ALKYLAMINO-PROPOXY)PHENYLALKYL]-4-PHENYLPIPERAZINES

There are disclosed compounds of the formula STR1 wherein R 1 is selected from the group consisting of lower alkyl; R 8 is selected from the group consisting of--O--(CH 2) n--wherein n is 2 to 20, STR2 and R 6 is selected from the group consisting of hydrogen or lower alkoxy, and STR3 wherein R 1 is selected from the group consisting of lower alkyl; R 8 is selected from the group consisting of--O--(CH 2) n--wherein n is 2 to 20, STR4 and R 6 is selected from the group consisting of hydrogen or lower alkoxy and racemates thereof.There are also disclosed processes and intermediates utilized to produce the end products. The end products have utility as agents exhibiting both α and selective β adrenergic blocking action.