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Usage

Uses

Used in Pharmaceutical Industry:
(2-Phenoxyphenyl)methanol is used as a key intermediate in the synthesis of triazolopyridines, which are known as myeloperoxidase inhibitors. Myeloperoxidase is an enzyme found in the immune system, and its overproduction has been linked to various inflammatory and autoimmune diseases. By inhibiting this enzyme, triazolopyridines can potentially alleviate the symptoms and progression of these conditions.
In the preparation of triazolopyridines, (2-Phenoxyphenyl)methanol serves as a crucial building block, providing the necessary phenolic and phenoxy moieties that are essential for the biological activity of the final product. The compound's reactivity and structural diversity make it an attractive candidate for the development of novel therapeutic agents targeting myeloperoxidase-related diseases.
Furthermore, the pharmaceutical industry may explore additional applications of (2-Phenoxyphenyl)methanol based on its unique chemical properties. For instance, its ability to form hydrogen bonds and engage in π-π interactions could be harnessed for the design of new drug candidates targeting various biological targets, such as receptors, enzymes, or ion channels.

InChI:InChI=1/C13H12O2/c14-10-11-6-4-5-9-13(11)15-12-7-2-1-3-8-12/h1-9,14H,10H2

Upstream product

• 19434-34-5 2-(phenoxy)benzaldehyde 
• 2243-42-7 2-phenoxybenzoic acid 
• 31462-52-9 bis-(2-phenoxybenzyl) oxalate 
• 39717-00-5 o-phenoxybenzyl acetate 
• 33838-32-3 potassium 2-formylphenolate 
• 62256-41-1 2-(4-nitrophenoxy)benzaldehyde 
• 88-67-5 2-Iodobenzoic acid 
• 108-95-2 phenol 
• 21905-56-6 methyl 2-phenoxybenzoate 
• 7487-88-9 magnesium sulfate 
• 60-29-7 diethyl ether 
• 13292-87-0 dimethyl sulfide borane 
• 1343478-55-6 2-PhOC₆H₄CH₂OTMS 
• 6630-33-7 ortho-bromobenzaldehyde 

Downstream Products

• 5888-53-9 2-phenoxybenzyl chloride 
• 120211-95-2 1-Methoxymethyl-2-phenoxy-benzene 
• 129952-68-7 1-[3-(2-chlorophenyl)propyl]-4-[1-oxo-2-[(2-phenoxyphenyl)methoxy]ethyl]piperazine 
• 148728-45-4 1-<3-(2-methoxyphenyl)propyl>-4-<1-oxo-2-<(2-phenoxyphenyl)methoxy>ethyl>piperazine 
• 31462-52-9 bis-(2-phenoxybenzyl) oxalate 
• 19434-34-5 2-(phenoxy)benzaldehyde 
• 39717-00-5 o-phenoxybenzyl acetate 
• 120211-93-0 N-(2-Phenoxy-benzyl)-acetamide 
• 61447-89-0 4,6-bis(4-methylpent-3-en-1-yl)-6-methylcyclohexa-1,3-diene-1-carbaldehyde 
• 25562-98-5 2-phenoxybenzyl cyanide 
• 25563-02-4 2-(2-phenoxyphenyl)acetic acid 
• 611-20-1 salicylonitrile 
• 132-64-9 dibenzofuran 
• 6476-32-0 o-phenoxybenzonitrile 

Relevant academic research and scientific papers

Synthesis of the Polycyclic Ring Systems of Artocarpol A and D

(Equation Presented) The first synthesis of the polycyclic ring systems of artocarpol A and D has been accomplished. These natural products were isolated recently from the root bark of Artocarpus rigida, and artocarpol A has been shown to have potent anti

AMINOPEPTIDASE A INHIBITORS AND PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME

The present invention relates to a novel compound, to a composition comprising the same, to methods for preparing the compound, and the use of this compound in therapy. In particular, the present invention relates to compound that is useful in the treatment and prevention of primary and secondary arterial hypertension, ictus, myocardial ischaemia, cardiac and renal insufficiency, myocardial infarction, peripheral vascular disease, diabetic proteinuria, Syndrome X and glaucoma.

Benzylic C?H Functionalisation by [Et3SiH+KOtBu] leads to Radical Rearrangements in o-tolyl Aryl Ethers, Amines and Sulfides

Reaction of Et3SiH+KOtBu with diaryl ethers, sulfides and amines that feature an ortho alkyl group leads to rearrangement products. The rearrangements arise from formation of benzyl radicals, likely formed through hydrogen atom abstraction by triethylsilyl radicals. The rearrangements involve cyclisation of the benzyl radical onto the partner arene, which, from computation, is the rate determining step. In the case of diaryl ethers, Truce-Smiles rearrangements arise from radical cyclisations to form 5-membered rings, but for diarylamines, cyclisations to form dihydroacridines are observed. (Figure presented.).

Optical Control of CRAC Channels Using Photoswitchable Azopyrazoles

The Ca2+ release-activated Ca2+ (CRAC) channels control many Ca2+-modulated physiological processes in mammals. Hyperactivating CRAC channels are known to cause several human diseases, including Stormorken syndrome. Here, we show the design of azopyrazole-derived photoswitchable CRAC channel inhibitors (designated piCRACs), which enable optical inhibition of store-operated Ca2+ influx and downstream signaling. Moreover, piCRAC-1 has been applied in vivo to alleviate thrombocytopenia and hemorrhage in a zebrafish model of Stormorken syndrome in a light-dependent manner.

In(OTf)3 catalyzed reductive etherification of 2-aryloxybenzaldehydes and 2-(arylthio)benzaldehydes

2-Aryloxybenzaldehydes and 2-(arylthio)benzaldehydes undergo reductive etherification in presence of 5 mol% In(OTf)3 and stoichiometric amount of Et3SiH under solvent free conditions to generate novel symmetrical dibenzyl ethers and thioethers in excellent yields. In(OTf)3 is found to be superior in terms of catalytic activity over the other metal triflates tested for the reaction. Xanthenes and thioxanthenes, as anticipated, could not be obtained under these conditions.

Cyclic analogue of S-benzylisothiourea that suppresses kynurenine production without inhibiting indoleamine 2,3-dioxygenase activity

Kynurenine is biosynthesised from tryptophan catalysed by indoleamine 2,3-dioxygenase (IDO). The abrogation of kynurenine production is considered a promising therapeutic target for immunological cancer treatment. In the course of our IDO inhibitor programme, formal cyclisation of the isothiourea moiety of the IDO inhibitor 1 afforded the 5-Cl-benzimidazole derivative 2b-6, which inhibited both recombinant human IDO (rhIDO) activity and cellular kynurenine production. Further derivatisation of 2b-6 provided the potent inhibitor of cellular kynurenine production 2i (IC50 = 0.34 μM), which unexpectedly exerted little effect on the enzymatic activity of rhIDO. Elucidation of the mechanism of action revealed that compound 2i suppresses IDO expression at the protein level by inhibiting STAT1 expression in IFN-γ-treated A431 cells. The kynurenine-production inhibitor 2i is expected to be a promising starting point for a novel approach to immunological cancer treatment.

Synthesis of targeted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines as potential lead molecules with promising anti-breast cancer activity

A targeted library of substituted dibenzo[b,f]thiepines and dibenzo[b,f]oxepines (prototypes I, II and III), and structurally analogous to tamoxifen have been synthesized as a new class of anti-breast cancer agents. All the prototype molecules exhibited potential antiproliferative activity against ER + ve and ER-ve breast cancer cell lines. Dibenzo[b,f]thiepine prototypes were found to be more active. Of all the compound tested, 14b exhibited potent in-vitro antiproliferative activity at 1.33 μM and 5 μM concentration in MCF-7 and MDA-MB-231 cell lines and was devoid of any cytotoxicity in normal HEK cells even at 50 μM. Cell cycle analysis showed that the compound 14b inhibited cell proliferation due to G0/G1 arrest in MCF-7 cells. Annexin-V FITC and PI staining experiments confirmed that the cell inhibition was primarily due to apoptosis and not by necrosis, which was also supported by LDH release assay experiment. Molecular docking studies showed better binding interaction of the new dibenzo[b,f]thiepine analogue 14b with the estrogen receptor (ER) as compared to 4-hydroxy-tamoxifen and this enhanced binding might be responsible for its estrogen antagonistic activity that induces cell cycle arrest, apoptosis and inhibition of breast cancer cells.

Synthesis, receptor affinity and effect on pentylenetetrazole-induced seizure threshold of novel benzodiazepine analogues: 3-Substituted 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles and 2-amino-5-(phenoxybenzyl)-1,3,4- oxadiazoles

The new series of 5-(2-phenoxybenzyl)-4H-1,2,4-triazoles, possessing C-3 thio, alkylthio and ethoxy substituents, and 2-amino-5-(2-phenoxybenzyl)-1,3,4- oxadiazoles were designed and synthesized as novel benzodiazepine analogues. Most of them revealed sim

An efficient dehydroxymethylation reaction by a palladium catalyst

A general method for selective dehydroxymethylation has been discovered by using widely available Pd(OAc)2. The present study offers a new synthetic strategy for the regioselective functionalization by employing the steric, electronic and coordinating nature of the hydroxymethyl (-CH 2OH) group temporarily.

Preparation, characterization and use of 1,3-disulfonic acid imidazolium hydrogen sulfate as an efficient, halogen-free and reusable ionic liquid catalyst for the trimethylsilyl protection of hydroxyl groups and deprotection of the obtained trimethylsilanes

Novel 1,3-disulfonic acid imidazolium hydrogen sulfate, a halogen-free ionic liquid, is a recyclable and eco-benign catalyst for the trimethylsilyl protection of hydroxyl groups at room temperature under solvent free conditions to afford trimethylsilanes in excellent yields (92-100%) and in very short reaction times (1-5 min). Deprotection of the resulting trimethylsilanes can also be achieved using the same catalyst in methanol. The catalyst was characterized by IR, 1H NMR, 13C NMR and MS studies. All the products were extensively characterized by IR, 1H NMR, MS, and elemental and melting point analyses. This new method consistently has the advantages of excellent yields and short reaction times. Further, the catalyst can be recovered and reused for several times without loss of activity. The work-up of the reaction consists of a simple separation, followed by concentration of the crude product and purification.