70625-29-5

Basic information

• Product Name: 2,3-dibromo-4,5-dimethoxybenzaldehyde
• Synonyms: 2,3-dibromo-4,5-dimethoxybenzaldehyde
• CAS NO: 70625-29-5
• Molecular Weight: 323.969
• Mol File: 70625-29-5.mol
• Article Data: 11

Chemical Properties

• CAS DataBase Reference: 2,3-dibromo-4,5-dimethoxybenzaldehyde(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3-dibromo-4,5-dimethoxybenzaldehyde(70625-29-5)
• EPA Substance Registry System: 2,3-dibromo-4,5-dimethoxybenzaldehyde(70625-29-5)

Safety Data

• Hazardous Substances Data: 70625-29-5(Hazardous Substances Data)

Usage

Physical state

White solid

Aromatic properties

Known for its aromatic properties

Common uses

Used as a building block in organic synthesis, production of pharmaceuticals and agrochemicals, creation of dyes and pigments, and synthesis of other organic compounds

Odor

Distinct odor

Flammability

Flammable

Toxicity

Toxic

Handling and storage

Requires proper handling and storage procedures

Upstream product

• 121-33-5 vanillin 
• 77-78-1 dimethyl sulfate 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 2973-75-3 5,6-dibromo-4-hydroxy-3-methoxybenzaldehyde 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 14045-41-1 2,3-dibromo-4,5-dihydroxybenzylaldehyde 
• 6948-30-7 5-bromoveratralaldehyde 

Downstream Products

• 149625-11-6 4,5-Dimethoxy-2,3-bis-propylsulfanyl-benzaldehyde 
• 134029-48-4 varacin 
• 149625-15-0 2-(4,5-Dimethoxy-2,3-bis-propylsulfanyl-phenyl)-ethylamine 
• 149625-14-9 1,2-Dimethoxy-5-((E)-2-nitro-vinyl)-3,4-bis-propylsulfanyl-benzene 
• 149625-16-1 [2-(4,5-Dimethoxy-2,3-bis-propylsulfanyl-phenyl)-ethyl]-carbamic acid 2-trimethylsilanyl-ethyl ester 
• 1260106-17-9 5,5'-oxybis(methylene)bis(3,4-dibromo-1,2-dimethoxybenzene) 
• 4950-08-7 (2,3-dibromo-4,5-dimethoxyphenyl)methanol 
• 74849-07-3 5-((2,3-dibromo-4,5-dihydroxybenzyloxy)methyl)-3,4-dibromobenzene-1,2-diol 
• 1383535-98-5 (2,3-dibromo-4,5-dimethoxyphenyl)(3,4-dimethoxyphenyl)methanone 
• 1383536-00-2 2,3-dibromo-1-(3,4-dimethoxybenzyl)-4,5-dimethoxybenzene 
• 1297595-96-0 3,4-dibromo-5-[2'-bromo-3',4'-dihydroxy-6'-(isobutoxymethyl)-benzyl]-benzene-1,2-diol 
• 1273542-60-1 2,3-dibromo-1-(2'-bromo-3',4'-dimethoxy-6'-methylbenzyl)-4,5-dimethoxy benzene 
• 1297595-97-1 2,3-dibromo-1-[2'-bromo-6'-(2-bromo-4,5-dimethoxybenzyl)-3',4'-dimethoxybenzyl]-4,5-dimethoxybenzene 
• 1297595-93-7 3,4-dibromo-5-[2'-bromo-3',4'-dihydroxy-6'-(propoxymethyl)-benzyl]-benzene-1,2-diol 

Relevant articles and documents

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Discovery of Novel Bromophenol-Thiosemicarbazone Hybrids as Potent Selective Inhibitors of Poly(ADP-ribose) Polymerase-1 (PARP-1) for Use in Cancer

Poly(ADP-ribose) polymerase-1 (PARP-1) is a new potential target for anticancer drug discovery. A series of bromophenol-thiosemicarbazone hybrids as PARP-1 inhibitors were designed, synthesized, and evaluated for their antitumor activities. Among them, the most promising compound, 11, showed excellent selective PARP-1 inhibitory activity (IC50 = 29.5 nM) over PARP-2 (IC50 > 1000 nM) and potent anticancer activities toward the SK-OV-3, Bel-7402 and HepG2 cancer cell lines (IC50 = 2.39, 5.45, and 4.60 μM), along with inhibition of tumor growth in an in vivo SK-OV-3 cell xenograft model. Further study demonstrated that compound 11 played an antitumor role through multiple anticancer mechanisms, including the induction of apoptosis and cell cycle arrest, cellular accumulation of DNA double-strand breaks, DNA repair alterations, inhibition of H2O2-triggered PARylation, antiproliferative effects via the production of cytotoxic reactive oxygen species, and autophagy. In addition, compound 11 displayed good pharmacokinetic characteristics and favorable safety. These observations demonstrate that compound 11 may serve as a lead compound for the discovery of new anticancer drugs.

Design, synthesis, and activity evaluation of novel N-benzyl deoxynojirimycin derivatives for use as α-glucosidase inhibitors

To obtain α-glucosidase inhibitors with high activity, 19 NB-DNJDs (N-benzyldeoxynojirimycin derivatives) were designed and synthesized. The results indicated that the 19 NBDNJDs displayed different inhibitory activities towards α-glucosidase in vitro. Compound 18a (1- (4-hydroxy-3-methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol) showed the highest activity, with an IC50 value of 0.207 ± 0.11 mM, followed by 18b (1-(3-bromo-4-hydroxy-5- methoxybenzyl)-2-(hydroxymethyl) piperidine-3,4,5-triol, IC50: 0.276 ± 0.13 mM). Both IC50 values of 18a and 18b were significantly lower than that of acarbose (IC50: 0.353 ± 0.09 mM). According to the structure-activity analysis, substitution of the benzyl and bromine groups on the benzene ring decreased the inhibition activity, while methoxy and hydroxyl group substitution increased the activity, especially with the hydroxyl group substitution. Molecular docking results showed that three hydrogen bonds were formed between compound 18a and amino acids in the active site of α- glucosidase. Additionally, an arene-arene interaction was also modelled between the phenyl ring of compound 18a and Arg 315. The three hydrogen bonds and the arene-arene interaction resulted in a low binding energy (-5.8 kcal/mol) and gave 18a a higher inhibition activity. Consequently, compound 18a is a promising candidate as a new α-glucosidase inhibitor for the treatment of type II diabetes.