70625-29-5

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

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

Downstream Products

• 149625-11-6 4,5-Dimethoxy-2,3-bis-propylsulfanyl-benzaldehyde 
• 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 
• 1297595-94-8 3,4-dibromo-5-[2'-bromo-3',4'-dihydroxy-6'-(isopropoxymethyl)-benzyl]-benzene-1,2-diol 
• 1297595-95-9 3,4-dibromo-5-[2'-bromo-6'-(butoxymethyl)-3',4'-dihydroxy-benzyl]-benzene-1,2-diol 
• 1238891-85-4 {3-bromo-2-[(2,3-dibromo-4,5-dimethoxyphenyl)methyl]-4,5-dimethoxyphenyl}methanol 
• 1297595-98-2 2,3-dibromo-1-(2′-bromo-6'-(3″,4″-dimethoxybenzyl)-3′,4′-dimethoxybenzyl)-4,5-dimethoxybenzene 
• 1258936-86-5 (2-bromo-3,4-dimethoxy-6-methylphenyl)-(2,3-dibromo-4,5-dimethoxyphenyl)-methanone 
• 1289128-35-3 (2'-bromo-6'-(dibromomethyl)-3',4'-dimethoxyphenyl)-(2,3-dibromo-4,5-dimethoxy phenyl)-methanone 

Relevant academic research and scientific papers

Antidiabetic activity in vitro and in vivo of BDB, a selective inhibitor of protein tyrosine phosphatase 1B, from Rhodomela confervoides

Background and Purpose: Protein tyrosine phosphatase (PTP) 1B (PTP1B) plays a critical role in the regulation of obesity, Type 2 diabetes mellitus and other metabolic diseases. However, drug candidates exhibiting PTP1B selectivity and oral bioavailability are currently lacking. Here, the enzyme inhibitory characteristics and pharmacological benefits of 3-bromo-4,5-bis(2,3-dibromo-4,5-dihydroxybenzyl)-1,2-benzenediol (BDB) were investigated in vitro and in vivo. Experimental Approach: Surface plasmon resonance (SPR) assay was performed to validate the direct binding of BDB to PTP1B, and Lineweaver–Burk analysis of the enzyme kinetics was used to characterise the inhibition by BDB. Both in vitro enzyme-inhibition assays and SPR experiments were also conducted to study the selectivity exhibited by BDB towards four other PTP-family proteins: TC-PTP, SHP-1, SHP-2, and LAR. C2C12 myotubes were used to evaluate cellular permeability to BDB. Effects of BDB on insulin signalling, hypoglycaemia and hypolipidaemia were investigated in diabetic BKS db mice, after oral gavage. The beneficial effects of BDB on pancreatic islets were examined based on insulin and/or glucagon staining. Key Results: BDB acted as a competitive inhibitor of PTP1B and demonstrated high selectivity for PTP1B among the tested PTP-family proteins. Moreover, BDB was cell-permeable and enhanced insulin signalling in C2C12 myotubes. Lastly, oral administration of BDB produced effective antidiabetic effects in spontaneously diabetic mice and markedly improved islet architecture, which was coupled with an increase in the ratio of β-cells to α-cells. Conclusion and Implications: BDB application offers a potentially practical pharmacological approach for treating Type 2 diabetes mellitus by selectively inhibiting PTP1B.

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 biological evaluation of bromophenol-thiazolylhydrazone hybrids inhibiting the interaction of translation initiation factors eIF4E/eIF4G as multifunctional agents for cancer treatment

The eukaryotic initiation factor 4E (eIF4E)is an emerging anticancer drug target for specific anticancer therapy as a promising approach to overcome drug resistance and promote chemotherapy antitumor efficacy. A series of bromophenol-thiazolylhydrazone hybrids were designed, synthesized and evaluated for their antitumor activities. Among of them, the most potent compound 3e (EGPI-1)could inhibit the eIF4E/eIF4G interaction. Further mechanism study demonstrated EGPI-1 played an antitumor role in multiple modes of action including regulating the activity of eIF4E by inhibiting the phosphorylation of eIF4E and 4EBP1, disrupting mitochondrial function through the mTOR/4EBP1 signaling pathway, and inducing autophagy, apoptosis and ROS generation. Moreover, EGPI-1 showed good safety and favorable pharmacokinetic properties in vivo. These observations demonstrate that EGPI-1 may serve as an excellent lead compound for the development of new anticancer drugs that target the eIF4E/eIF4G interface and as a chemical genetic probe to investigate the role of the eIF4E in biological processes and human diseases.

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.

Design, synthesis and biological evaluation of novel pyrimidinedione derivatives as DPP-4 inhibitors

A series of novel pyrimidinedione derivatives were designed and evaluated for in vitro dipeptidyl peptidase-4 (DPP-4) inhibitory activity and in vivo anti-hyperglycemic efficacy. Among them, the representative compounds 11, 15 and 16 showed excellent inhibitory activity of DPP-4 with IC50 values of 64.47 nM, 188.7 nM and 65.36 nM, respectively. Further studies revealed that compound 11 was potent in vivo hypoglycemic effect. The structure–activity relationships of these pyrimidinedione derivatives had been discussed, which would be useful for developing novel DPP-4 inhibitors as treating type 2 diabetes.

Nine PTP1B inhibitors and synthesis method and application thereof

The invention relates to a chemical total synthesis method of nine novel PTP1B inhibitors and application of the nine novel PTP1B inhibitors in medicine for treating type 2 diabetes. According to the PTP1B inhibitors, one or two or more of nine compounds serve as active ingredients, and the structural formulas of the nine compounds are shown in the specification. By means of the compounds, the sensitivity of insulin receptors can be enhanced by inhibiting the activity of PTP1B, and a good treatment effect is achieved for insulin resistance type 2 diabetes.

PTP1B INHIBITORS, SYNTHESIS THEREOF AND APPLICATION THEREOF IN PREPARATION OF MEDICAMENTS FOR TREATING TYPE 2 DIABETES MELLITUS

The present invention relates to chemical total synthesis methods of six novel protein tyrosine phosphatase-1B (PTP1B) inhibitors and application of the inhibitors in the preparation of medicaments for treating type 2 diabetes mellitus (T2DM). The PTP1B inhibitors use one or more of the six compounds represented by the structural formulae 1, 2, 3, 4, 5 and 6, as active components. The compounds can enhance the sensitivity of an insulin receptor by inhibiting the activity of PTP1B, thereby having a favorable therapeutic effect on insulin-resistant T2DM.

Synthesis and α-glucosidase inhibitory mechanisms of bis(2,3-dibromo-4,5-dihydroxybenzyl) ether, a potential marine bromophenol α-glucosidase inhibitor

Bis(2,3-dibromo-4,5-dihydroxybenzyl) ether (BDDE), derived from the marine algae, is a potential α-glucosidase inhibitor for type 2 diabetes treatment. In the present study, a synthetic route was established as a valid approach to obtain BDDE. Fluorescence spectra, circular dichroism spectra and molecular docking methods were employed to elucidate the inhibitory mechanisms of BDDE against α-glucosidase. The results showed that BDDE could be prepared effectively and efficiently with the established synthetic methods. Synthetic BDDE bound with α-glucosidase and induced minor conformational changes of the enzyme. The docking results indicated the interaction between BDDE and α-glucosidase was driven by both hydrophobic forces and hydrogen bonds. The docked BDDE molecule was completely buried in the α-glucosidase binding pocket with part of the molecule reaching the catalytic center and overlapping with the position of glucose, and the rest of the molecule extending towards protein surface. This study provides useful information for the understanding of the BDDE-α-glucosidase interaction and for the development of novel α-glucosidase inhibitors.

Expedient routes to valuable bromo-5,6-dimethoxyindole building blocks

The synthesis of 3-, 4-, 7-bromo and 4,7-dibrominated 5,6-dihydroxyindole (DHI) and 5,6-dihydroxyindole-2-carboxylic acid (DHICA) derivatives is reported. Hemetsberger and Bartoli indole syntheses were investigated and expedient routes to the desired compounds were developed. These indoles are valuable substrates for elaboration using transition metal-mediated cross-coupling chemistry.

Cephem compounds, and antibacterial agents

Novel cephem compounds represented by a formula [I] and pharmacologically admissible salts or capable of physiologically hydrolyzable nontoxic esters thereof are disclosed. STR1 [wherein R1 indicates a straight-chain or branched lower alkyl gro