1860-58-8

Usage

Uses

Used in Pharmaceutical Industry:
(3-Benzyloxy-phenyl)-acetic acid is used as a key intermediate in the synthesis of various pharmaceuticals for its anti-inflammatory and analgesic properties. It aids in the development of medications targeting pain and inflammation-related disorders, offering potential therapeutic benefits to patients.
Used in Agrochemical Industry:
In the agrochemical sector, (3-Benzyloxy-phenyl)-acetic acid serves as a crucial component in the production of agrochemicals. Its incorporation enhances the effectiveness of these products, contributing to improved crop protection and yield.
Used in Research and Development:
(3-Benzyloxy-phenyl)-acetic acid is utilized as a research compound in laboratories. Its diverse applications in the pharmaceutical and agrochemical industries make it an essential tool for scientists to explore new drug development and agrochemical formulations.
Used in Immunomodulation Studies:
(3-Benzyloxy-phenyl)-acetic acid is employed in research aimed at understanding its potential role in modulating immune responses. This knowledge can contribute to the advancement of immunotherapies and treatments for immune-related conditions.

InChI:InChI=1/C15H14O3/c16-15(17)10-13-7-4-8-14(9-13)18-11-12-5-2-1-3-6-12/h1-9H,10-11H2,(H,16,17)

Upstream product

• 139377-33-6 phenylmethyl 2-[3-(phenylmethoxy)phenyl]acetate 
• 20967-96-8 2-(3-benzyloxyphenyl)acetonitrile 
• 100-39-0 benzyl bromide 
• 62969-42-0 3-benzyloxy-phenylacetic acid methyl ester 
• 42058-59-3 3-hydroxy-benzeneacetic acid, methyl ester 
• 124-38-9 carbon dioxide 
• 22446-38-4 ethyl 3-hydroxyphenylacetate 
• 621-37-4 m-hydroxyphenylacetic acid 
• 1700-30-7 (3-(benzyloxy)phenyl)methanol 
• 620-24-6 3-Hydroxybenzyl alcohol 
• 130604-43-2 ethyl 3-(benzyloxyphenyl)acetate 
• 24033-03-2 1-benzyloxy-3-chloromethylbenzene 
• 1700-37-4 3-Benzyloxybenzaldehyde 
• 100-83-4 meta-hydroxybenzaldehyde 

Downstream Products

• 90736-63-3 N-<2-(3-methoxyphenyl)ethyl>-m-benzyloxyphenylacetamide 
• 645386-03-4 N-[2-(3-benzyloxyphenyl)ethyl]aniline 
• 645386-00-1 2-[3-(benzyloxy)phenyl]-N-phenylacetamide 
• 844431-34-1 N-[2-(3-benzyloxy-phenyl)-ethyl]-4-iodo-N-phenyl-benzamide 
• 844431-35-2 6-benzyloxy-1-(4-iodophenyl)-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 844431-67-0 6-benzyloxy-2-phenyl-1-(4-pyridin-4-yl-phenyl)-1,2,3,4-tetrahydro-isoquinoline 
• 844431-40-9 6-benzyloxy-1-[4-(3,4-dimethylpiperazin-1-yl)phenyl]-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 844431-39-6 6-benzyloxy-1-[4-(4-methylpiperazin-1-yl)phenyl]-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 844431-37-4 6-benzyloxy-1-[4-(3-methylpiperazin-1-yl)phenyl]-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 938078-71-8 6-benzyloxy-1-[4-(1-methyl-piperidin-4-yl)-phenyl]-2-phenyl-1,2,3,4-tetrahydro-isoquinoline 
• 844431-38-5 6-benzyloxy-1-[4-(3-ethylpiperazin-1-yl)phenyl]-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 844431-41-0 6-benzyloxy-1-[4-(4-ethyl-3-methylpiperazin-1-yl)phenyl]-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 844431-42-1 6-benzyloxy-1-[4-(3-ethyl-4-methylpiperazin-1-yl)phenyl]-2-phenyl-1,2,3,4-tetrahydroisoquinoline 
• 844431-36-3 2-[4-(6-benzyloxy-2-phenyl-1,2,3,4-tetrahydro-isoquinolin-1-yl)-phenyl]-octahydro-pyrido[1,2-a]pyrazine 

Relevant academic research and scientific papers

TETRAHYDRONAPHTHALENE AND TETRAHYDROISOQUINOLINE DERIVATIVES AS ESTROGEN RECEPTOR DEGRADERS

The present disclosure relates to bifunctional compounds, which find utility as modulators of estrogen receptor (target protein). In particular, the present disclosure is directed to bifunctional compounds, which contain on one end at least one of a Von Hippel-Lindau ligand, a cereblon ligand, Inhibitors of Apoptosis Proteins ligand, mouse double-minute homolog 2 ligand, or a combination thereof, which binds to the respective E3 ubiquitin ligase, and on the other end a moiety which binds the target protein, such that the target protein is placed in proximity to the ubiquitin ligase to effect degradation (and inhibition) of target protein. The present disclosure exhibits a broad range of pharmacological activities associated with degradation/inhibition of target protein. Diseases or disorders that result from aggregation or accumulation of the target protein are treated or prevented with compounds and compositions of the present disclosure.

Nickel-Catalyzed Carboxylation of Benzylic C-N Bonds with CO2

A user-friendly Ni-catalyzed reductive carboxylation of benzylic C-N bonds with CO2 is described. This procedure outperforms state-of-the-art techniques for the carboxylation of benzyl electrophiles by avoiding commonly observed parasitic pathways, such as homodimerization or β-hydride elimination, thus leading to new knowledge in cross-electrophile reactions.

Glucosylceramide synthase inhibitors

The invention relates to inhibitors of glucosylceramide synthase (GCS) useful for the treatment metabolic diseases, such as lysosomal storage diseases, either alone or in combination with enzyme replacement therapy, and for the treatment of cancer.

Enantioselective Oxidative Aerobic Dealkylation of N-Ethyl Benzylisoquinolines by Employing the Berberine Bridge Enzyme

N-Dealkylation methods are well described for organic chemistry and the reaction is known in nature and drug metabolism; however, to our knowledge, enantioselective N-dealkylation has not been yet reported. In this study, exclusively the (S)-enantiomers o

Designing new analogs for streamlining the structure of cytotoxic lamellarin natural products

Despite the therapeutic potential of marine-derived lamellarin natural products, their preclinical development has been hampered by their lipophilic nature, causing very poor aqueous solubility. In order to develop more drug-like analogs, their structure was streamlined in this study from both the cytotoxic activity and lipophilicity standpoints. First, a modified total synthetic route was successfully devised to construct a library of 59 systematically designed lamellarin analogs, which were then subjected to cytotoxicity and log P determinations. Along with the 25 first-generation lamellarins previously synthesized in our laboratory, the structure-activity and structure-lipophilicity relationships were extensively evaluated. Our results clearly indicated the additional structural requirements around the lamellarin skeleton which, when combined with those reported previously, can provide invaluable guidance for further modifications to increase the aqueous solubility of these compounds.

Vitamin D3 analogues that contain modified A- and seco-B-rings as hedgehog pathway inhibitors

The hedgehog (Hh) signaling pathway is a developmental signaling pathway that has been implicated as a target for anti-cancer drug development in a variety of human malignancies. Several natural and synthetic vitamin D-based seco-steroids have been identified as potent inhibitors of Hh signaling with chemotherapeutic potential. These include the previously characterized analogue 4, which contains the northern CD-ring/side chain region of vitamin D3 (VD3) linked to an aromatic A-ring mimic through an ester bond. To further explore structure-activity relationships for this class of VD3-based Hh pathway inhibitors, we have designed, synthesized and evaluated several series of compounds that modify the length, composition, and stereochemical orientation of the ester linker. These studies have identified compounds 54 and 55, which contain an amine linker and an aromatic A-ring incorporating a para-phenol, as new lead compounds with enhanced potency against the Hh pathway (IC50 values Combining double low line 0.40 and 0.32 μM, respectively).

1,2,3-Triazole-containing uracil derivatives with excellent pharmacokinetics as a novel class of potent human deoxyuridine triphosphatase inhibitors

Deoxyuridine triphosphatase (dUTPase) has emerged as a potential target for drug development as a 5-fluorouracil-based combination chemotherapy. We describe the design and synthesis of a novel class of human dUTPase inhibitors, 1,2,3-triazole-containing u

Biocatalytic enantioselective oxidative C-C coupling by aerobic C-H activation

Bridging the gap: The berberine bridge enzyme (BBE) was employed for the first preparative oxidative biocatalytic C-C coupling that leads to a new intramolecular bond. This unique transformation requires O2 as sole stoichiometric oxidant and gives access to novel optically pure (S)-berbine 2 and (R)-1-benzyl-1,2,3,4-tetrahydroisoquinoline 1 alkaloid derivatives by kinetic resolution.

Biocatalytic organic synthesis of optically pure (S)-scoulerine and berbine and benzylisoquinoline alkaloids

A chemoenzymatic approach for the asymmetric total synthesis of the title compounds is described that employs an enantioselective oxidative C-C bond formation catalyzed by berberine bridge enzyme (BBE) in the asymmetric key step. This unique reaction yielded enantiomerically pure (R)-benzylisoquinoline derivatives and (S)-berbines such as the natural product (S)-scoulerine, a sedative and muscle relaxing agent. The racemic substrates rac-1 required for the biotransformation were prepared in 4-8 linear steps using either a Bischler-Napieralski cyclization or a C1-Cα alkylation approach. The chemoenzymatic synthesis was applied to the preparation of fourteen enantiomerically pure alkaloids, including the natural products (S)-scoulerine and (R)-reticuline, and gave overall yields of up to 20% over 5-9 linear steps.

Synthesis and evaluation of azetidinone analogues of combretastatin A-4 as tubulin targeting agents

The synthesis and antiproliferative activity of a new series of rigid analogues of combretastatin A-4 are described which contain the 1,4-diaryl-2-azetidinone (β-lactam) ring system in place of the usual ethylene bridge present in the natural combretastatin stilbene products. These novel compounds are also substituted at position 3 of the β-lactam ring with an aryl ring. A number of analogues showed potent nanomolar activity in human MCF-7 and MDA-MB-231 breast cancer cell lines, displayed in vitro inhibition of tubulin polymerization, and did not cause significant cytotoxicity in normal murine breast epithelial cells. 4-(4-Methoxyaryl)-substituted compound 32, 4-(3-hydroxy-4-methoxyaryl)-substituted compounds 35 and 41, and the 3-(4-aminoaryl)-substituted compounds 46 and 47 displayed the most potent antiproliferative activity of the series. β-Lactam 41 in particular showed subnanomolar activity in MCF-7 breast cancer cells (IC50 = 0.8 nM) together with significant in vitro inhibition of tubulin polymerization and has been selected for further biochemical assessment. These novel β-lactam compounds are identified as potentially useful scaffolds for the further development of antitumor agents that target tubulin.