724-98-1

Usage

Uses

Used in Pharmaceutical Industry:
2-(Phenoxymethyl)benzoic acid is used as an active pharmaceutical ingredient for its anti-inflammatory and analgesic properties, making it a candidate for the development of medications aimed at reducing inflammation and pain.
Used in Organic Synthesis:
In the field of organic chemistry, 2-(Phenoxymethyl)benzoic acid serves as a key intermediate in the synthesis of various organic compounds, contributing to the creation of a wide range of chemical products.

InChI:InChI=1/C14H12O3/c15-14(16)13-9-5-4-6-11(13)10-17-12-7-2-1-3-8-12/h1-9H,10H2,(H,15,16)/p-1

Upstream product

• 87-41-2 2-benzofuran-1(3H)-one 
• 139-02-6 sodium phenoxide 
• 7115-91-5 2-ethoxycarbonylbenzyl bromide 
• 108-95-2 phenol 
• 18982-54-2 o-bromobenzyl alcohol 
• 578-51-8 2-bromobenzylchloride 
• 118-90-1 ortho-methylbenzoic acid 
• 168551-49-3 2-(phenoxymethyl)benzaldehyde 
• 4122-56-9 methyl o-formylbenzoate 
• 100-67-4 potassium phenolate 
• 4504-85-2 2-Phenoxymethyl-benzoic acid ethyl ester 
• 87-24-1 ethyl 2-methylbenzoate 
• 612-20-4 2-(hydroxymethyl)benzoic acid 
• 643-79-8 o-phthalic dicarboxaldehyde 

Downstream Products

• 87-41-2 2-benzofuran-1(3H)-one 
• 108-95-2 phenol 
• 1354017-80-3 C₃₃H₄₃NO₄S 
• 1354017-70-1 (R)-2-(2-(phenoxymethyl)benzamido)-3-(((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)thio)propanoic acid 
• 1668-19-5 doxepin 
• 27678-61-1 11-(4-Methylpiperazino)-6,11-dihydrodibenzooxepin 
• 3607-34-9 (E)-doxepin 
• 1668-19-5 (Z)-doxepin 
• 21733-94-8 2-phenoxymethylbenzoyl chloride 
• 77175-92-9 (2-chloromethyl-benzyl)-phenyl ether 
• 1229-29-4 doxepin hydrochloride 

Relevant academic research and scientific papers

Preparation method of benzyl aryl ether and application of benzyl aryl ether in synthesis

and, 6-dihydrodibenzo [11 - b] oxazepine e -11 - ketone compounds are synthesized through a one-step reaction of benzaldehyde compounds and phenolic compounds through one-step reaction. The benzyl aryl ether and 6 and 11 -dihydrodibenzo [b, e] oxazepine -11 - ketone compound respectively have a chemical structure formula shown in a formula I and II. The invention discloses a synthesis method of the compound. Benzaldehyde compound After completion of the reaction, I, 6-dihydrodibenzo [11 - b] oxazepine e ketone compound -11 - can be synthesized through an oxidation or hydrolysis step and a ring closing step after the reaction is complete II.

Synthesis, characterization, and biologic activity of new acyl hydrazides and 1,3,4-oxadiazole derivatives

Starting from isoniazid and carboxylic acids as precursors, thirteen new hydrazides and 1,3,4-oxadiazoles of 2-(4-substituted-phenoxymethyl)-benzoic acids were synthesized and characterized by appropriate means. Their biological properties were evaluated in terms of apoptosis, cell cycle blocking, and drug metabolism gene expression on HCT-8 and HT-29 cell lines. In vitro antimicrobial tests were performed by the microplate Alamar Blue assay for the anti-mycobacterial activities and an adapted agar disk diffusion technique for other non-tubercular bacterial strains. The best antibacterial activity (anti-Mycobacterium tuberculosis effects) was proved by 9. Compounds 7, 8, and 9 determined blocking of G1 phase. Compound 7 proved to be toxic, inducing apoptosis in 54percent of cells after 72 h, an effect that can be predicted by the increased expression of mRNA caspases 3 and 7 after 24 h. The influence of compounds on gene expression of enzymes implicated in drug metabolism indicates that synthesized compounds could be metabolized via other pathways than NAT2, spanning adverse effects of isoniazid. Compound 9 had the best antibacterial activity, being used as a disinfectant agent. Compounds 7, 8, and 9, seemed to have antitumor potential. Further studies on the action mechanism of these compounds on the cell cycle may bring new information regarding their biological activity.

Iron(II) promoted direct synthesis of dibenzo[b,e]oxepin-11(6H)-one derivatives with biological activity. A short synthesis of doxepin

A novel and efficient synthesis of dibenzo[b,e]oxepin-11(6H)-ones by direct intramolecular ortho-acylation from readily available 2-(phenoxymethyl)benzoic acids was developed. The method takes advantage of a newly developed cooperative system consisting of sustainable FeCl2 and Cl2CHOCH3 as the key components. This methodology is compatible with a wide variety of functional groups in good to excellent yields and high regioselectivity. The synthetic application of new protocol was extended to the synthesis of known tricyclic drug doxepin as well as a small library of oxepin based derivatives. For the first time, the obtained dibenzo[b,e]oxepinone derivatives were evaluated for their biological activities on the free-living nematode Caenorhabditis elegans as an effective and cost-efficient model system for anthelmintic discovery.

Method for preparing doxepin hydrochloride using o-halogen methyl methyl benzoate as raw material

The present invention discloses a method for preparing doxepin hydrochloride using o-halogen methyl methyl benzoate as a raw material. In the method, o-halogen methyl methyl benzoate which is wide in source is used as a starting raw material, and sulfasalazine is obtained through substitution, hydrolysis, cyclization, nucleophilic addition, elimination reaction, nucleophilic substitution and neutralization reaction. The method comprises: during a nucleophilic substitution reaction obtained in the seventh step, using an organic lithium compound in an ether solution, so that the organic lithium compound and dimethylamine form an ammonium lithium salt (the formula is as shown in the description); then conducting an alkylation reaction on the ammonium lithium salt and a halide to improve the yield of tertiary amine, thereby ensuring the yield and purity of doxepin hydrochloride.

A to phthaldialdehyde as the raw material to synthesize method of doxepin hydrochloride (by machine translation)

This invention discloses in a to phthaldialdehyde as the raw material to synthesize method of doxepin hydrochloride. The method comprises in a wide range of sources phthaldialdehyde as the starting material, reaction by sequentially connie Zha Luo, intramolecular esterification, substituted, cyclized, nucleophilic addition, elimination reactions, nucleophilic substitution, pro-nuclear substituted, and in the reaction, to obtain liu Danhuang pyridine. In section 8 step in the nucleophilic substitution reaction steps, yu Mi using organic lithium compound in the solvent, so that the organic compound forming ammonium lithium salt with dimethylamine , Then this ammonium lithium salt for carrying out the alkylation reaction with halo, improve the yield of the addition, the ultimate so as to guarantee the yield and purity of doxepin hydrochloride. Phthaldialdehyde cheap, so as to reduce the production cost. (by machine translation)

Synthetic method of doxepin hydrochloride adopting o-halogen methyl benzoate as raw material

The invention discloses a synthetic method of doxepin hydrochloride adopting o-halogen methyl benzoate as a raw material. The synthetic method comprises: taking the o-methyl benzoate wide in source as a starting raw material, and sequentially carrying out benzyl halogenations, substitution, hydrolysis, cyclization, nucleophilic addition, nucleophilic substitution and neutralization to obtain salazosulfapyridine. In the nucleophilic substitution step of step 7, an organic lithium compound is dissolved in an ether solvent, so that the organic lithium compound and dimethylamine react to form an ammonium lithium salt (see the description), then the ammonium lithium salt is subjected to alkylation reaction with a halogen compound, the yield of the tertiary ammonium is increased, and the yield and purity of the final doxepin hydrochloride can be guaranteed.

Dibenzo[b,f][1,4]oxazepines and dibenzo[b,e]oxepines: Influence of the chlorine substitution pattern on the pharmacology at the H1R, H4R, 5-HT2AR and other selected GPCRs

Inspired by VUF6884 (7-Chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine), reported as a dual H1/H4 receptor ligand (pKi: 8.11 (human H1R (hH1R)), 7.55 (human H4R (hH4R))), four known and 28 new oxazepine and related oxepine derivatives were synthesised and pharmacologically characterized at histamine receptors and selected aminergic GPCRs. In contrast to the oxazepine series, within the oxepine series, the new compounds showed high affinity to the hH1R (pKi: 6.8–8.7), but no or moderate affinity to the hH4R (pKi: ≤ 5.3). For one oxepine derivative (1-(2-Chloro-6,11-dihydrodibenzo[b,e]oxepin-11-yl)-4-methylpiperazine), the enantiomers were separated and the R-enantiomer was identified as the eutomer at the hH1R (pKi: 8.83 (R), 7.63 (S)) and the guinea-pig H1R (gpH1R) (pKi: 8.82 (R), 7.41 (S)). Molecular dynamic studies suggest that the tricyclic core of the compounds is bound in a similar mode into the binding pocket, as described for doxepine in the hH1R crystal structure. Moreover, docking studies of all oxepine derivatives at the hH1R indicate that the oxygen and the position of the chlorine in the tricyclic core determines, if the R- or the S-enantiomer is the eutomer. For some of the oxazepines and oxepines the affinity to other aminergic GPCRs is in the same range as to hH1R or hH4R, thus, those compounds have to be classified as dirty drugs. However, one oxazepine derivative (3,7-Dichloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine was identified as dual hH1/h5-HT2A receptor ligand (pKi: 9.23 (hH1R), 8.74 (h5-HT2AR), ≤7 at other analysed GPCRs), whereas one oxepine derivative (1-(3,8-Dichloro-6,11-dihydrodibenzo[b,e]oxepin-11-yl)-4-methylpiperazine) was identified as selective hH1R antagonist (pKi: 8.44 (hH1R), ≤6.7 at other analyzed GPCRs). Thus, the pharmacological results suggest that the oxazepine/oxepine moiety and additionally the chlorine substitution pattern toggles receptor selectivity and specificity.

COMPOUNDS AND METHODS FOR USE IN TREATING NEOPLASIA AND CANCER

The present invention relates to a novel method for the treatment of neoplasia, including cancer and other diseases and conditions in humans and mammals. More particularly, in preferred aspects, the present invention provides a method for the use of novel compounds for the treatment of neoplasia, hyperproliferative cell growth including psoriasis, restenosis following cardiovascular surgery, hyperplasia, including renal hyperplasia, chronic inflammatory diseases including rheumatoid and osteoarthritis, among others.

Amide-modified prenylcysteine based Icmt inhibitors: Structure-activity relationships, kinetic analysis and cellular characterization

Human protein isoprenylcysteine carboxyl methyltransferase (hIcmt) is the enzyme responsible for the α-carboxyl methylation of the C-terminal isoprenylated cysteine of CaaX proteins, including Ras proteins. This specific posttranslational methylation event has been shown to be important for cellular transformation by oncogenic Ras isoforms. This finding led to interest in hIcmt inhibitors as potential anti-cancer agents. Previous analog studies based on N-acetyl-S-farnesylcysteine identified two prenylcysteine-based low micromolar inhibitors (1a and 1b) of hIcmt, each bearing a phenoxyphenyl amide modification. In this study, a focused library of analogs of 1a and 1b was synthesized and screened versus hIcmt, delineating structural features important for inhibition. Kinetic characterization of the most potent analogs 1a and 1b established that both inhibitors exhibited mixed-mode inhibition and that the competitive component predominated. Using the Cheng-Prusoff method, the K i values were determined from the IC50 values. Analog 1a has a KIC of 1.4 ± 0.2 μM and a KIU of 4.8 ± 0.5 μM while 1b has a KIC of 0.5 ± 0.07 μM and a KIU of 1.9 ± 0.2 μM. Cellular evaluation of 1b revealed that it alters the subcellular localization of GFP-KRas, and also inhibits both Ras activation and Erk phosphorylation in Jurkat cells.

Doxepin analogs and methods of use thereof

The invention relates to novel antihistamines and methods of modulating sleep by administering a doxepin analog or a pharmaceutically effective salt thereof.