50773-56-3

Usage

Uses

Used in Pharmaceutical Industry:
3-Benzyloxy-4-hydroxybenzaldehyde is used as a reactant for the preparation of various inhibitors, including PDE4 and PDE7 inhibitors, which play a crucial role in regulating inflammatory responses and other cellular processes. Its application in this area is due to its ability to modulate the activity of these enzymes, potentially leading to the development of new therapeutic agents for treating conditions related to inflammation and other enzyme dysregulations.
Additionally, 3-Benzyloxy-4-hydroxybenzaldehyde is used as a reactant in the synthesis of insulin-like growth-factor-I receptor (IGF-IR) inhibitors. These inhibitors are important for targeting the IGF-IR signaling pathway, which is often dysregulated in various cancers and has been implicated in tumor growth and progression. 3-Benzyloxy-4-hydroxybenzaldehyde's structural features make it a valuable building block for designing and developing novel IGF-IR inhibitors.
Furthermore, 3-Benzyloxy-4-hydroxybenzaldehyde is utilized in the preparation of ferulic acid derivatives as xanthine oxidase inhibitors. Xanthine oxidase is an enzyme involved in the purine metabolism pathway, and its inhibition can be beneficial in treating conditions like gout and reducing oxidative stress. 3-Benzyloxy-4-hydroxybenzaldehyde's reactivity and functional groups make it suitable for the development of such inhibitors.

Upstream product

• 100-44-7 benzyl chloride 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 855273-14-2 1-(3-benzyloxy-4-hydroxy-phenyl)-2,2,2-trichloro-ethanol 
• 100-39-0 benzyl bromide 
• 402573-75-5 3-benzyloxy-4-(4-methoxybenzyloxy)benzaldehyde 
• 114688-53-8 3-(benzyloxy)-4-(methoxymethoxy)benzaldehyde 
• 4049-39-2 4-benzyloxy-3-hydroxy-benzaldehyde 
• 621-59-0 isovanillin 
• 120-80-9 benzene-1,2-diol 
• 67-66-3 chloroform 
• 6272-38-4 O-benzylcatechol 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 

Downstream Products

• 159832-34-5 3-benzyloxy-4-hydroxy-benzoic acid 
• 6346-05-0 3-benzyloxy-4-methoxybenzaldehyde 
• 309721-36-6 (1R,2S)-4-benzyloxy-3-[2,3-epoxy-1-(4-benzyloxyphenyl)-propoxyl]benzaldehyde 
• 309721-40-2 (1S,2R)-4-benzyloxy-3-[2,3-epoxy-1-(4-benzyloxyphenyl)-propoxyl]benzaldehyde 
• 419572-58-0 4-[(2S,5S)-5-(1-benzenesulfonyl-1-nitroethyl)-2,5-dihydrofuran-2-yloxy]-3-benzyloxybenzaldehyde 
• 868671-93-6 3-benzyloxy-4-hydroxy-trans-cinnamic acid methyl ester 
• 118563-37-4 3-Benzyloxy-4-hydroxy-5-phenylsulfanylmethyl-benzaldehyde 
• 115125-01-4 (E)-3-(3-Benzyloxy-4-hydroxy-5-phenylsulfanylmethyl-phenyl)-2-cyano-acrylamide 
• 99896-31-8 3-benzyloxy-4-isopropyloxybenzaldehyde 
• 628330-16-5 ethyl (E)-3-[3-benzyloxy-4-(methoxymethoxy)phenyl]propenoate 
• 1234500-50-5 4-isobutoxy-3-benzyloxybenzaldehyde 
• 934682-38-9 3-benzyloxy-4-hydroxycinnamic acid ethyl ester 
• 1146696-35-6 (2R,3R)-epicatechin-4'-O-β-D-glucuronic acid 
• 1390644-12-8 (2R,3R)-epicatechin 4'-O-α-D-glucuronic acid 

Relevant academic research and scientific papers

Dendrimer disassembly by benzyl ether depolymerization

The disassembly of dendritic structures was realized by a cascade cleavage reaction triggered by an initially stimulated group in the dendrimer periphery. A depolymerizable backbone was engineered into prototypical dendritic structures. Evidence for the completion of the disassembly process is provided by the absorbance peak of the p-nitrophenoxide ion that was intentionally installed at the focal point of the dendrons. Observation of the UV spectra during the disassembly process supports a stepwise cascade cleavage proceeding from the periphery into the core. Copyright

Scalable Asymmetric Syntheses of Foslevodopa and Foscarbidopa Drug Substances for the Treatment of Parkinson's Disease

Foslevodopa (FLD, levodopa 4′-monophosphate, 3) and foscarbidopa (FCD, carbidopa 4′-monophosphate, 4) were identified as water-soluble prodrugs of levodopa (LD, 1) and carbidopa (CD, 2), respectively, which are useful for the treatment of Parkinson's disease. Herein, we describe asymmetric syntheses of FLD (3) and FCD (4) drug substances and their manufacture at pilot scale. The synthesis of FLD (3) employs a Horner-Wadsworth-Emmons olefination reaction followed by enantioselective hydrogenation of the double bond as key steps to introduce the α-amino acid moiety with the desired stereochemistry. The synthesis of FCD (4) features a Mizoroki-Heck reaction followed by enantioselective hydrazination to install the quaternary chiral center bearing a hydrazine moiety.

Total synthesis of leontopodioside A

Leontopodioside A, isolated from the whole plants of Leontopodium leontopodioides, possesses significant α-glucosidase inhibitory activity. In this work, we studied the total synthesis of leontopodioside A by two strategies for the first time. The optimized strategy involved nine linear steps and has an overall yield of 16.1%. The key feature of the strategy is that glycosylation of chalcone acceptor first followed by the cyclization to construct the flavone scaffold, which has general applicability for the synthesis of flavonoid glycosides.

Drug compound for treating hepatopathy and application thereof

The invention discloses a drug compound for treating hepatopathy and application thereof. The drug compound specifically serves as a compound shown in general formula (I) or an optical isomer or a pharmaceutically-acceptable salt of the compound. The compound or the optical isomer or the pharmaceutically-acceptable salt of the compound has a good curative effect and low toxicity on hepatopathy, especially fatty liver. Experiments show that the compound has an obvious protective effect on zebrafish nonalcoholic fatty liver, so that the drug compound has a good application prospect in medicinesfor treatment or prevention of hepatopathy, especially fatty liver or liver fibrosis or liver cirrhosis.

Synthesis of a Photo-Caged DOPA Derivative by Selective Alkylation of 3,4-Dihydroxybenzaldehyde

Natural and synthetic polymers containing the catechol moiety of noncoded amino acid 3,4-dihydroxyphenylalanine (DOPA) are capable of metal-coordination and adhesion under wet conditions. Masking the catechol subunit with a photo-cleavable group would provide an opportunity to design tunable adhesion properties that are especially important for biomaterial and biomedicine applications. Herein, we report the regioselective synthesis of a photo-caged DOPA bearing an ortho-nitrobenzyl (oNB) group that is capable of undergoing cleavage upon irradiation with UV light. We developed a selective synthetic route towards a 3-O-oNB alkylated DOPA regioisomer that can be readily incorporated into proteins by using a previously developed bio-expression platform. The synthesis is based on a regioselectivity switch in 3,4-dihydrozybenzaldehyde alkylation upon application of different equivalents of deprotonating base. The enantiomerically pure 3-O-oNB-DOPA was prepared on a gram scale and proved to be generally compatible with the solid-phase peptide synthesis conditions. We also demonstrate the general applicability of the developed synthetic strategy by providing the synthesis of 3-O-methyl-DOPA.

PYRROLOBENZODIAZEPINES AND CONJUGATES THEREOF

A conjugate of formula (A): Wherein Y is selected from formulae A1 and A2: Z1 is a C1-3 alkylene group; Z2 is a C1-3 alkylene group; Q is: where QX is such that Q is an amino-acid residue, a dipeptide residue or a tripeptide residue; L is a linker connected to a cell binding agent; CBA is the cell binding agent; and n is an integer between 0 and 48.

A Corey–Seebach Macrocyclisation Strategy for the Synthesis of Riccardin C and an Unnatural Macrocyclic Bis(bibenzyl) Analogue

A total synthesis of riccardin C has been accomplished using a Corey–Seebach reaction to effect macrocyclisation. The versatility of the strategy has also been demonstrated with a mimetic synthesis of an unnatural bis(bibenzyl) analogue.

Design, synthesis and anti-proliferative effects in tumor cells of new combretastatin A-4 analogs

Abstract A total of 11 novel combretastatin A-4 (CA-4) analogs were designed, synthesized, and evaluated for the anti-proliferative effects in tumor cells. The compounds represent four structural classes: (i) hydrogenated derivatives, (ii) ethoxyl derivatives, (iii) amino derivatives and (iv) pro-drugs. Biological evaluations demonstrate that multiple structural features control the biological potency. Three of the compounds, sit-1, sit-2 and sit-3, have potent anti-proliferative activity against multiple cancer cell lines. Their pro-drugs were synthesized to increase water solubility. Structure-activity relationship study and Surflex-Docking were studied in this paper. These results will be useful for the design of new CA-4 analogs that are structurally related to the SAR study.

Unexpected copper mediated benzyl O→O migration during an Ullmann ether coupling

The synthesis of a highly functionalized phenolic diaryl ether 5,5′-oxybis(4-hydroxy-3-methoxybenzaldehyde) (1) potentially interesting as a new scaffold for drug design, has been carried out using Ullmann coupling conditions. An unusual benzyl migration in o-benzyloxyphenol moiety occurred during this reaction leading to an unexpected compound identified as 4-(benzyloxy)-3-(2-(benzyloxy)-4-formyl-6-methoxyphenoxy)-5-methoxy benzaldehyde (7). A rationale for this migration process is proposed.

NOVEL FLAVONOID COMPOUNDS AND USES THEREOF

The present disclosure provides a compound of the following formula, racemates, enantiomers, prodrugs and salts thereof: Formula (I). Also provided is the use of these compounds for the treatment of ischemia and reperfusion injuries. Further applications include the treatment of diseases caused by cell apoptosis and / or cell necrosis.