55142-16-0

Usage

Uses

Used in Fragrance Industry:
METHYL 2-BENZYLOXYBENZOATE is used as a fixative in perfumes for its ability to enhance and prolong the scent of other fragrance components, providing a more enduring and complex aroma.
Used in Flavor Industry:
In the flavor industry, METHYL 2-BENZYLOXYBENZOATE is used as a flavoring agent in food products, imparting a subtle sweetness and a hint of jasmine flavor, which can enhance the taste profile of various culinary creations.
Used in Pharmaceutical Production:
METHYL 2-BENZYLOXYBENZOATE is utilized in the production of pharmaceuticals, where it may contribute to the development of new drugs or serve as a key component in the synthesis of existing medications.
Used as a Chemical Intermediate in Organic Synthesis:
In the realm of organic synthesis, METHYL 2-BENZYLOXYBENZOATE serves as a valuable chemical intermediate, facilitating the creation of a range of organic compounds for various applications, including the development of new materials and the improvement of existing ones.
It is essential to adhere to proper handling and storage procedures for METHYL 2-BENZYLOXYBENZOATE to ensure safety and prevent any potential harm or adverse effects, as is the case with any chemical substance.

InChI:InChI=1/C15H14O3/c1-17-15(16)13-9-5-6-10-14(13)18-11-12-7-3-2-4-8-12/h2-10H,11H2,1H3

Upstream product

• 7631-93-8 sodium o-methoxycarbonylphenolate 
• 100-44-7 benzyl chloride 
• 119-36-8 methyl salicylate 
• 606-45-1 2-methoxybenzoic acid methyl ester 
• 20194-18-7 sodium phenyl-methanolate 
• 100-39-0 benzyl bromide 
• 68-12-2 N,N-dimethyl-formamide 
• 14389-86-7 2-benzyloxybenzoic acid 
• 74-88-4 methyl iodide 
• 69-72-7 salicylic acid 
• 67-56-1 methanol 

Downstream Products

• 856814-53-4 1-(2-benzyloxy-phenyl)-3-(2,6-dimethoxy-phenyl)-propane-1,3-dione 
• 873556-51-5 dimethyl 2-(2-(benzyloxy)phenyl)-2-oxoethylphosphonate 
• 119-36-8 methyl salicylate 
• 380335-36-4 2-benzyloxybenzoic acid hyrdrazide 
• 14389-86-7 2-benzyloxybenzoic acid 

Relevant academic research and scientific papers

Template-Hopping Approach Leads to Potent, Selective, and Highly Soluble Bromo and Extraterminal Domain (BET) Second Bromodomain (BD2) Inhibitors

A number of reports have recently been published describing the discovery and optimization of bromo and extraterminal inhibitors which are selective for the second bromodomain (BD2); these include our own work toward GSK046 (3) and GSK620 (5). This paper describes our approach to mitigating the genotoxicity risk of GSK046 by replacement of the acetamide functionality with a heterocyclic ring. This was followed by a template-hopping and hybridization approach, guided by structure-based drug design, to incorporate learnings from other BD2-selective series, optimize the vector for the amide region, and explore the ZA cleft, leading to the identification of potent, selective, and bioavailable compounds 28 (GSK452), 39 (GSK737), and 36 (GSK217).

Polyhydrazide-Based Organic Nanotubes as Efficient and Selective Artificial Iodide Channels

Reported herein is a series of pore-containing polymeric nanotubes based on a hydrogen-bonded hydrazide backbone. Nanotubes of suitable lengths, possessing a hollow cavity of about a 6.5 ? diameter, mediate highly efficient transport of diverse types of anions, rather than cations, across lipid membranes. The reported polymer channel, having an average molecular weight of 18.2 kDa and 3.6 nm in helical height, exhibits the highest anion-transport activities for iodide (EC50=0.042 μm or 0.028 mol % relative to lipid), whcih is transported 10 times more efficiently than chlorides (EC50=0.47 μm). Notably, even in cholesterol-rich environment, iodide transport activity remains high with an EC50 of 0.37 μm. Molecular dynamics simulation studies confirm that the channel is highly selective for anions and that such anion selectivity arises from a positive electrostatic potential of the central lumen rendered by the interior-pointing methyl groups.

Design, synthesis and biological activity of selective hCAs inhibitors based on 2-(benzylsulfinyl)benzoic acid scaffold

A large library of derivatives based on the scaffold of 2-(benzylsulfinyl)benzoic acid were synthesised and tested as atypical inhibitors against four different isoforms of human carbonic anhydrase (hCA I, II, IX and XII, EC 4.2.1.1). The exploration of the chemical space around the main functional groups led to the discovery of selective hCA IX inhibitors in the micromolar/nanomolar range, thus establishing robust structure-activity relationships within this versatile scaffold. HPLC separation of some selected chiral compounds and biological evaluation of the corresponding enantiomers was performed along with molecular modelling studies on the most active derivatives.

Discovery, synthesis and anti-atherosclerotic activities of a novel selective sphingomyelin synthase 2 inhibitor

The sphingomyelin synthase 2 (SMS2) is a potential target for pharmacological intervention in atherosclerosis. However, so far, few selective SMS2 inhibitors and their pharmacological activities were reported. In this study, a class of 2-benzyloxybenzamides were discovered as novel SMS2 inhibitors through scaffold hopping and structural optimization. Among them, Ly93 as one of the most potent inhibitors exhibited IC50 values of 91 nM and 133.9 μM against purified SMS2 and SMS1 respectively. The selectivity ratio of Ly93 was more than 1400-fold for purified SMS2 over SMS1. The in vitro studies indicated that Ly93 not only dose-dependently diminished apoB secretion from Huh7 cells, but also significantly reduced the SMS activity and increased cholesterol efflux from macrophages. Meanwhile, Ly93 inhibited the secretion of LPS-mediated pro-inflammatory cytokine and chemokine in macrophages. The pharmacokinetic profiles of Ly93 performed on C57BL/6J mice demonstrated that Ly93 was orally efficacious. As a potent selective SMS2 inhibitor, Ly93 significantly decreased the plasma SM levels of C57BL/6J mice. Furthermore, Ly93 was capable of dose-dependently attenuating the atherosclerotic lesions in the root and the entire aorta as well as macrophage content in lesions, in apolipoprotein E gene knockout mice treated with Ly93. In conclusion, we discovered a novel selective SMS2 inhibitor Ly93 and demonstrated its anti-atherosclerotic activities in vivo. The preliminary molecular mechanism-of-action studies revealed its function in lipid homeostasis and inflammation process, which indicated that the selective inhibition of SMS2 would be a promising treatment for atherosclerosis.

Metal-free Synthesis of Spiro-2,2′-benzo[b]furan-3,3′-ones via PhI(OAc)2-Mediated Cascade Spirocyclization

Treating the benzyl protected 3-hydroxy-1,3-bis(2-hydroxyphenyl)prop-2-en-1-ones solely with PhI(OAc)2 (PIDA) in DCE at room temperature readily furnished the seldom studied spiro-2,2′-benzo[b]furan-3,3′-ones in satisfactory to excellent yields. The hypervalent iodine reagent enables the metal-free cascade spirocyclization resulting in the dual oxidative C?O bond formation. (Figure presented.).

Total Synthesis of Mycobacterium tuberculosis Dideoxymycobactin-838 and Stereoisomers: Diverse CD1a-Restricted T Cells Display a Common Hierarchy of Lipopeptide Recognition

Mycobacterium tuberculosis produces dideoxymycobactin-838 (DDM-838), a lipopeptide that potently activates T cells upon binding to the MHC-like antigen-presenting molecule CD1a. M. tuberculosis produces DDM-838 in only trace amounts and a previous solid-phase synthesis provided sub-milligram quantities. We describe a high-yielding solution-phase synthesis of DDM-838 that features a Mitsunobu substitution that avoids yield-limiting epimerization at lysine during esterification, and amidation conditions that prevent double-bond isomerization of the Z-C20:1 acyl chain, and provides material with equivalent antigenicity to natural DDM-838. Isomers of DDM-838 that varied in stereochemistry at the central lysine and the C20:1 acyl chain were compared for their ability to be recognised by CD1a-restricted T cell receptors (TCRs). These TCRs, derived from unrelated human donors, exhibited a similar spectrum of reactivity towards the panel of DDM-838 isomers, highlighting the exquisite sensitivity of lipopeptide-reactive T cells for the natural DDM stereochemistry.

2-ALKYLOXY BENZENE FORMYL ARYLAMINE COMPOUND AND PHARMACEUTICAL USE THEREOF

The present invention relates to 2-alkoxy benzene formyl arylamine compounds as scheme I , in which the R, G, X, Y, Z are consistent with the detailed description in the patent claim. The compounds can act as sphingomyelin synthase (SMS) inhibitors to treat diseases caused by abnormal increasing of sphingomyelin(SM). This invention also includes compounds as scheme I , their pharmaceutically acceptable salts, pharmaceutical compositions as the active ingredients, and their application in drugs which can prevent and cure diseases caused by SM level abnormal increase. These diseases include atherosclerosis, fatty liver, obesity, type II diabetes, and other metabolic syndromes.

Solubility and thermodynamic analysis of N′-(1-(N-(methyl) benzylaminomethyl)-2-oxoindolin-3-ylidene)-2-(benzyloxy) benzohydrazide in different neat solvents at different temperatures

The present study was undertaken to determine the solubilities of newly synthesized anticancer compound N′-(1-(N-(methyl) benzylaminomethyl)-2-oxoindolin-3-ylidene)-2-(benzyloxy) benzohydrazide (NMBOBB) in nine different neat solvents including water, isopropanol (IPA), ethanol, ethylene glycol (EG), 1.2-propanediol (PG), 1-butanol, 2-butanol, polyethylene glycol-400 (PEG-400) and Transcutol (diethylene glycol monoethyl ether) at T = 298.15 K to 318.15 K and p = 0.1 MPa. Experimental solubility data of NMBOBB was fitted with Apelblat and ideal models. The mole fraction solubility of NMBOBB was recorded highest in PEG-400 (1.14 × 10- 2 at T = 318.15 K) followed by Transcutol (7.14 × 10- 3 at T = 318.15 K), 2-butanol (1.45 × 10- 3 at T = 318.15 K), 1-butanol (1.38 × 10- 3 at T = 318.15 K), ethanol (9.69 × 10- 4 at T = 318.15 K), PG (9.52 × 10- 4 at T = 318.15 K), IPA (9.41 × 10- 4 at T = 318.15 K), EG (8.09 × 10- 4 at T = 318.15 K) and water (3.00 × 10- 6 at T = 318.15 K). The highest solubility of NMBOBB in PEG-400 was possible due to lower polarity and higher molar mass of PEG-400. The dissolution behavior of NMBOBB was observed as an endothermic, spontaneous and an entropy-driven due to positive values of standard enthalpies, Gibbs free energies and entropies in all nine neat solvents investigated. The results of this work would be helpful in purification, recrystallization and dosage form design of NMBOBB.

Target β-catenin/CD44/Nanog axis in colon cancer cells by certain N′-(2-oxoindolin-3-ylidene)-2-(benzyloxy)benzohydrazides

Cell surface molecule CD44 plays a major role in regulation of cancer stem cells CSCs on both phenotypic and functional level, however chemical inhibition approach of CD44 to targets CSCs is poorly studied. Herein, we report the discovery of certain N′-(2-oxoindolin-3-ylidene)-2-(benzyloxy)benzohydrazides as a novel inhibitor of CD44. Molecular docking study showed interference of the scaffold of these compounds with β-catenin/TCF-4 complex, building a direct relationship between CD44 inhibition and observed well-fitted binding domain. Compound 11a, most potent member elicits inhibition effect on TCF/LEF reporter activity conformed the involvement of Wnt pathway inhibition as a mechanism of action. Furthermore, the treatment by the mentioned compound leads to inhibition of embryonic transcriptional factor Nanog but not Sox2 or Oct-4 suggested specific targeted effect. Moreover, the cytotoxicity and cell cycle effect of this series seems to be dependent on CD44 expression.

LANTHANIDE CLUSTERS AND METHODS OF USE THEREOF

The present invention is directed to multinuclear lanthanides chiral clusters, based on phenyl-oxazoline-amide (POxA) ligands, and to methods of use thereof. The chiral clusters of this invention are highly fluorescent with high stability.