14045-41-1

Usage

Uses

Used in Organic Synthesis:
2,3-DIBROMO-4,5-DIHYDROXYBENZALDEHYDE is used as a reagent in organic synthesis for its ability to participate in various chemical reactions, contributing to the formation of new compounds.
Used in Pharmaceutical Production:
In the pharmaceutical industry, 2,3-DIBROMO-4,5-DIHYDROXYBENZALDEHYDE is used as a key intermediate in the synthesis of various pharmaceuticals and fine chemicals, playing a crucial role in the development of new drugs and medicinal compounds.
Used as a Building Block in the Chemical Industry:
2,3-DIBROMO-4,5-DIHYDROXYBENZALDEHYDE serves as a valuable building block in the chemical industry, enabling the creation of a wide range of organic compounds for diverse applications.

InChI:InChI=1/C7H4Br2O3/c8-5-3(2-10)1-4(11)7(12)6(5)9/h1-2,11-12H

Upstream product

• 70625-29-5 2,3-dibromo-4,5-dimethoxybenzaldehyde 
• 121-33-5 vanillin 
• 2973-76-4 5-bromo-4-hydroxy-3-methoxybenzaldehyde 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 2973-75-3 5,6-dibromo-4-hydroxy-3-methoxybenzaldehyde 

Relevant academic research and scientific papers

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.

Bromophenol-pyrazoline compound as well as synthesis method and application thereof (by machine translation)

The invention relates to a compound, in particular to a bromophenol-pyrazoline compound as well as a synthesis method and application thereof. The bromophenol-pyrazoline compound has the following structural general formula: The bromophenol-pyrazoline compound provided by the invention has high-efficiency main protease MPro Activity can be inhibited, and the replication of coronavirus can be disturbed in cells, so that the compound has the efficacy of treating coronavirus pneumonia, and has wide application prospects in preparation of medicines for treating coronavirus pneumonia. (by machine translation)

The first synthesis of phenylpropanoid derivative bromophenols including natural products: Formation of an indene derivative compound

Synthesis of the natural bromophenols 3,4-dibromo-5-(butoxymethyl)benzene-1,2-diol, (E)-3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-methylacrylaldehyde (7), 3,4-dibromo-5-(3-hydroxy-2-methylpropyl)benzene-1,2-diol and 3-(2,3-dibromo-4,5-dihydroxyphenyl)-2-pheny

Toward a treatment of diabesity: In vitro and in vivo evaluation of uncharged bromophenol derivatives as a new series of PTP1B inhibitors

Protein tyrosine phosphatase 1B (PTP1B) has been considered as a validated biological target for type 2 diabetes treatment, but past endeavors to develop inhibitors of PTP1B into drugs have been unsuccessful. Two challenging aspects are selective inhibition and cell permeability. A structure-based strategy was employed to develop uncharged bromophenols as a new series of PTP1B inhibitors. The most potent compound 22 (LXQ46) inhibited PTP1B with an IC50 value of 0.190 μM, and showed remarkable selectivity over other protein tyrosine phosphatases (PTPs, 20–200 folds). In the SPR study, increasing concentrations of compound 22 led to concentration-dependent increases in binding responses, indicating that compound 22 could bind to the surface of PTP1B via noncovalent means. By treating insulin-resistant C2C12 myotubes with compound 22, enhanced insulin and leptin signaling pathways were observed. Long-term oral administration of compound 22 reduced the blood glucose level of diabetic BKS db mice. The glucose tolerance tests (OGTT) and insulin tolerance tests (ITT) in BKS db mice showed that oral administration of compound 22 could increase insulin sensitivity. In addition, long-term oral administration of compound 22 could protect mice from obesity, which was not the result of toxicity. Our pharmacokinetics results from the rat-based assays showed that orally administered compound 22 was absorbed rapidly from the gastrointestinal tract, extensively distributed to the tissues, and rapidly eliminated from the body. All these results indicate that compound 22 could serve as a qualified agent to treat type II diabetes.

Bromophenol-oxazole compound and its use in drug for treatment on diabetes mellitus type 2

The invention relates to a chemical total synthesis method of novel bromophenol-oxazole PTP1B and its use in a drug for treatment on diabetes mellitus type 2. The PTP1B inhibitor has a structural formula shown in the description. The compound improves insulin receptor sensibility through inhibiting the activity of protein tyrosine phosphatase 1B and has good treatment effects on insulin resistance-type diabetes mellitus type 2.

In-vitro cytotoxic activities of the major bromophenols of the red alga Polysiphonia lanosa and some novel synthetic isomers

Bioassay-guided fractionation was applied to the cytotoxic chloroform fraction of the red alga Polysiphonia lanosa. The major compounds of the most active fraction were identified using GLC-MS analysis as lanosol (1), methyl, ethyl, and n-propyl ethers of lanosol (1a, 1b, and 1c, respectively), and aldehyde of lanosol (2), although 1b appears to be an artifact arising during the fractionation procedure. These compounds and other known bromophenols were synthesized in addition to four novel isomers (3, 3a-c). The cytotoxic activities of all the synthetic compounds were determined against DLD-1 cells using the MTT assay. Compounds with IC50 50 = 1.72 and 0.80 μmol, respectively), and its effect on the cell cycle was studied using flow cytometry.

Synthesis of some hydroxymethylbromophenols of marine origin

The hydroxymethylbromophenols 5, 7 and 9, isolated from marine source have been prepared in good yield.The bromo derivatives 1 and 2 of vanillin are demethylated to 4 and 6 which on borohydride reduction furnish 5 and 7 respectively.The dibromo-p-cresol (3) is oxidised to the aldehyde 8 which on borohydride reduction affords 9.