61559-82-8

Usage

General Description

1,2-Benzenediol, 3-bromo-6-methoxy- is a chemical compound that belongs to the category of benzenediols. It is also known as 3-bromo-6-methoxy-catechol. 1,2-Benzenediol, 3-bromo-6-methoxy- is a derivative of catechol, with a bromine atom and a methoxy group attached to the benzene ring. It is commonly used in organic synthesis and pharmaceutical research due to its potential pharmacological properties. 1,2-Benzenediol, 3-bromo-6-methoxy- has also been studied for its antioxidant and anti-inflammatory activities, making it of interest in the development of new drugs and treatments. Additionally, it may have applications in biochemical research and as a building block in the synthesis of other organic compounds.

Upstream product

• 20035-41-0 6-bromo-2-hydroxy-3-methoxybenzaldehyde 
• 934-00-9 3-methocycatechol 
• 104-92-7 1-bromo-4-methoxy-benzene 
• 37942-01-1 5-bromo-2-methoxyphenol 
• 159263-87-3 2-acetyloxy-3-methoxy-6-bromobenzaldehyde 
• 148-53-8 3-methoxy-2-hydroxybenzaldehyde 
• 7150-01-8 2-acetoxy-3-methoxybenzaldehyde 

Downstream Products

• 203259-23-8 2,3-dibenzyloxy-4-methoxy-1-bromobenzene 
• 290347-62-5 1-bromo-4-methoxy-2,3-bis(methoxymethoxy)-benzene 
• 878293-50-6 1-iodo-4-methoxy-2,3-bis(methoxymethoxy)benzene 
• 109971-63-3 (Z)-3-methoxy-6-(3,4,5-trimethoxystyryl)benzene-1,2-diol 
• 109971-64-4 Combretastatin B₁ 
• 444992-83-0 1-methoxy-2,3-bis(methoxymethoxy)-4-((3,4,5-trimethoxyphenyl)-ethynyl)benzene 
• 203259-18-1 [(2S,3S)-1-Benzoyl-4-(2,3-bis-benzyloxy-4-methoxy-phenyl)-2-hydroxymethyl-2,3-dihydro-1H-pyrrol-3-yl]-acetic acid tert-butyl ester 
• 203259-13-6 (2S,3S)-1-Benzoyl-4-(2,3-bis-benzyloxy-4-methoxy-phenyl)-3-tert-butoxycarbonylmethyl-2,3-dihydro-1H-pyrrole-2-carboxylic acid methyl ester 
• 203259-12-5 C₂₁H₂₁BO₅ 
• 23731-55-7 4-methoxy-2,3-methylenedioxy-benzaldehyde 
• 190661-82-6 5-bromo-8-methoxy-2,3-dihydrobenzo[b][1,4]dioxine 
• 61535-22-6 1-bromo-4-methoxy-2,3-methylenedioxybenzene 
• 1622437-83-5 2-benzoyl-4-(5,8-dimethoxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-phenylbutane-1,4-dione 
• 1622430-95-8 1-(5,8-dihydroxy-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-phenylpropane-1,3-dione 

Relevant academic research and scientific papers

GAMMA-DIKETONES AS WNT/BETA -CATENIN SIGNALING PATHWAY ACTIVATORS

The present disclosure provides γ-diketones or analogs thereof, that activate Wnt/β-catenin signaling and thus treat or prevent diseases related to signal transduction, such as osteoporosis and osteoarthropathy; osteogenesis imperfecta, bone defects, bone fractures, periodontal disease, otosclerosis, wound healing, craniofacial defects, oncolytic bone disease, traumatic brain injuries or spine injuries, brain atrophy/neurological disorders related to the differentiation and development of the central nervous system, including Parkinson's disease, strokes, ischemic cerebral disease, epilepsy, Alzheimer's disease, depression, bipolar disorder, schizophrenia; otic disorders like cochlear hair cell loss; eye diseases such as age related macular degeneration, diabetic macular edema or retinitis pigmentosa and diseases related to differentiation and growth of stem cell, such as hair loss, hematopoiesis related diseases and tissue regeneration related diseases.

HETEROAROMATIC COMPOUNDS AND THEIR USE AS DOPAMINE D1 LIGANDS

The present invention provides, in part, compounds of Formula I: and pharmaceutically acceptable salts thereof and N-oxides thereof; processes and intermediates for preparation of; and compositions and uses thereof. The present invention further provides D1 agonists with reduced D1R desensitization, D1 agonists with a reduced β- arrestin recruitment activity relative to Dopamine, D1 agonists interacting significantly with the Ser188 but not significantly with the Ser202 of a D1R when binding to the D1R, D1 agonists interacting less strongly with the Asp103 and interacting less strongly with the Ser198 of a D1R when binding to the D1R, and their uses.

BIARYL PHOSPHODIESTERASE 1NHIBITORS

Novel biaryl compounds with phosphodiesterase inhibitory activity of the general formula (I), wherein R1, R2, R3, X, Y, Z1, Z2, Z3, and Z4 have the meanings defined herein, as well as their use as therapeutic agents in the treatment of inflammatory diseases and conditions

Broonsted acid-promoted hydrocyanation of arylalkenes

Nonactivated arylalkenes are effectively converted to tertiary benzylic nitriles in the presence of triflic acid and trimethylsilyl cyanide. The hydrocyanation reactions result in good to excellent yield when electron-donating groups are substituted on the benzene ring. The reaction conditions are mild and relatively safe, notably without need for handling hazardous hydrogen cyanide gas, providing simple and easy access to tertiary benzylic nitriles. The reaction was applied to the preparation of a PDE4 inhibitor (3) as well as a series of analogues.

Synthesis of combretastatins A-1 and B-1

Combretastatins A-1 and B-1 have been synthesized by coupling MOM-protected p-iodomethoxycatechol with 3,4,5-trimethoxyphenylacetylene in a Sonogashira reaction.

Combretastatin analogs with tubulin binding activity

Analogs of combretastatin have been discovered which demonstrate impressive cytotoxicity as well as a remarkable ability to inhibit tubulin polymerization. Such compounds are excellent clinical candidates for the treatment of cancer in humans. In addition, certain of these ligands, as pro-drugs, may well prove to be tumor selective vascular targeting chemotherapeutic agents or to have vascular targeting activity resulting in the selective prevention and/or destruction of nonmalignant proliferating vasculature.

Hydroxyphenstatin and the prodrugs thereof

The benzophenone derivative of combretastatin A-1, designated “hydroxyphenstatin”, was synthesized by compiling a protected bromobenzene and a benzaldehyde to form a benzhydrol which was subsequently oxidized to the ketone. Hydroxyphenstatin was converted

Direct biooxidation of arenes to corresponding catechols with E. coli JM109 (pDTG602). Application to synthesis of combretastatins A-1 and B-1

Convergent syntheses of combretastatins A-1 and B-1 were accomplished via coupling of biocatalytically generated p-bromomethoxycatechol with trimethoxyphenylacetylene.

Medium-scale preparation of useful metabolites of aromatic compounds via whole-cell fermentation with recombinant organisms

The whole-cell fermentation of aromatic coumpounds with Escherichia coli JM109 (pDTG601) on a medium scale (10-15L) produces enantiopure cyclohexadienediols. A detailed procedure for the fermentation is described, and yields for several metabolites are provided. A similar procedure using E. coli JM109 (pDTG602) affords catechols. The dienediols are useful for asymmetric synthesis, and several important targets originating from these metabolites are tabulated.

Antineoplastic agents. 443. Synthesis of the cancer cell growth inhibitor hydroxyphenstatin and its sodium diphosphate prodrug

A structure - activity relationship (SAR) study of the South African willow tree (Combretum caffrum) antineoplastic constituent combretastatin A-4 (3b) led to the discovery of a potent cancer cell growth inhibitor designated phenstatin (5a). This benzophenone derivative of combretastatin A-4 showed remarkable antineoplastic activity, and the benzophenone derivative of combretastatin A-1 was therefore synthesized. The benzophenone, designated hydroxyphenstatin (6a), was synthesized by coupling of a protected bromobenzene and a benzaldehyde to give the benzhydrol with subsequent oxidation to the ketone. Hydroxyphenstatin was converted to the sodium phosphate prodrug (6e) by a dibenzyl phosphite phosphorylation and subsequent benzyl cleavage (6a → 6d → 6e). While hydroxyphenstatin (6a) was a potent inhibitor of tubulin polymerization with activity comparable to that of combretastatin A-1 (3a), the phosphorylated derivative (6e) was inactive.