116096-91-4

Usage

Uses

Used in Organic Synthesis:
3,5-DIBROMO-2,4-DIHYDROXYBENZALDEHYDE is used as a building block in organic synthesis for the preparation of various biologically active molecules. Its presence of bromine and hydroxyl groups allows for versatile chemical reactions, making it a key component in the creation of complex organic compounds.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 3,5-DIBROMO-2,4-DIHYDROXYBENZALDEHYDE is used as a valuable intermediate in the development of new drugs. Its unique structure and functional groups contribute to the design and synthesis of potential therapeutic agents.
Used in Agrochemical Development:
3,5-DIBROMO-2,4-DIHYDROXYBENZALDEHYDE also plays a role in the agrochemical industry, where it is utilized in the synthesis of compounds with pesticidal properties, contributing to the development of effective crop protection agents.
Used in Antimicrobial Applications:
3,5-DIBROMO-2,4-DIHYDROXYBENZALDEHYDE has been studied for its potential antimicrobial properties, making it a candidate for use in applications that require the inhibition of microbial growth, such as in the development of antimicrobial agents.
Used in Antioxidant Formulations:
Due to its antioxidant potential, 3,5-DIBROMO-2,4-DIHYDROXYBENZALDEHYDE can be used in the formulation of antioxidant products, which are important for various applications, including health supplements and industrial processes where oxidation needs to be controlled.
Used in Anticancer Research:
3,5-DIBROMO-2,4-DIHYDROXYBENZALDEHYDE is also being investigated for its potential anticancer properties, with the aim of developing new therapeutic agents for the treatment of various types of cancer.

Upstream product

• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 108-46-3 recorcinol 

Downstream Products

• 672938-13-5 7-acetoxy-6,8-dibromo-3-phenyl-coumarin 
• 117238-61-6 3,5-dibromo-2-hydroxy-4-methoxy benzaldehyde 
• 860553-67-9 3,5-dibromo-4-hydroxy-2-methoxybenzaldehyde 
• 860725-02-6 3,5-dibromo-2,4-dimethoxy-benzaldehyde 
• 182427-46-9 2,4-dihydroxy-3,5-dimethoxybenzaldehyde 
• 839731-19-0 3,5-dibromo-4-hydroxy-[2-(2-napthalenamine)aceto]benzoic acid hydrazide 
• 672938-12-4 6,8-dibromo-7-hydroxy-3-phenyl-coumarin 
• 328921-82-0 4-tert-butyl-benzoic acid (3,5-dibromo-2,4-dihydroxy-benzylidene)-hydrazide 
• 1147840-42-3 biphenyl-4-carboxylic acid (3,5-dibromo-2,4-dihydroxy-benzylidene)-hydrazide 
• 1147839-75-5 furan-2-carboxylic acid (3,5-dibromo-2,4-dihydroxy-benzylidene)-hydrazide 
• 328586-05-6 thiophene-2-carboxylic acid (3,5-dibromo-2,4-dihydroxybenzylidene)-hydrazide 
• 331649-59-3 nicotinic acid (3,5-dibromo-2,4-dihydroxy-benzylidene)-hydrazide 
• 342002-58-8 benzoic acid (3,5-dibromo-2,4-dihydroxy-benzylidene)-hydrazide 
• 330639-84-4 isonicotinic acid (3,5-Dibromo-2,4-dihydroxy-benzylidene)-hydrazide 

Relevant academic research and scientific papers

Two-photon uncaging with the efficient 3,5-dibromo-2,4-dihydroxycinnamic caging group

(Chemical Equation Presented) An optical syringe for targeted delivery of a substrate in vivo has been developed on the basis of the 3,5-dibromo-2,4- dihydroxycinnamic caging group. Two-photon excitation of the caged compound uncages the substrate (ethano

Total synthesis of altissimacoumarin D, a small molecule sirtuin1 activator

The total synthesis of the plant natural product altissimacoumarin D was achieved by the Mitsunobu alkylation of isofraxidin by geraniol. Isofraxidin was prepared from 2,4-dihydroxybenzaldehyde in five steps. The key reaction was the Knoevenagel condensat

Pyridinium bromochromate: A new and efficient reagent for bromination of hydroxy aromatics

Pyridinium bromochromate (PBC) has been used as an efficient and selective nuclear brominating agent for bromination of various substituted hydroxy-acetophenones, aldehydes and phenols.

3-substituted coumarin derivative and application and GPR35 receptor agonist

The invention discloses a 3-substituted coumarin derivative and a pharmaceutically acceptable salt, a solvate, a hydrate or a crystal form. The compound of the invention generally exhibits high agonistic activity against human G protein-coupled receptor 35 (GPR35) and is specific agonists of the human GPR35 receptor. The compound provided by the invention is an active ligand of the novel GPR35 receptor, and the compound and the pharmaceutically acceptable salt, the solvate, the hydrate or the crystal form thereof generally exhibit higher activity and good selectivity to the human GPR35. The 3-substituted coumarin derivative is the specific agonist of the GPR35 receptor and can be used in the preparation of a medicament for treating, preventing and inhibiting a disease mediated by the GPR35receptor.

Discovery of 2H-Chromen-2-one Derivatives as G Protein-Coupled Receptor-35 Agonists

A family of 2H-chromen-2-one derivatives were identified as G protein-coupled receptor-35 (GPR35) agonists using dynamic mass redistribution assays in HT-29 cells. The compounds with 1H-tetrazol-5-yl in 3-substituted position displayed higher potency than the corresponding carboxyl analogs, and the hydroxyl group in the 7-position also played an important role in GPR35 agonistic activity. 6-Bromo-7-hydroxy-8-nitro-3-(1H-tetrazol-5-yl)-2H-chromen-2-one (50) was found to be the most potent GPR35 agonist with an EC50 of 5.8 nM. Calculating the physicochemical properties of compounds with moderate to high potency suggested that compounds 30, 50, and 51 showed good druggability. This study provides a novel series of GPR35 agonists, and compound 50 may be a powerful tool to study GPR35.

Discovery and mechanism study of SIRT1 activators that promote the deacetylation of fluorophore-labeled substrate

SIRT1 is an NAD+-dependent deacetylase, whose activators have potential therapeutic applications in age-related diseases. Here we report a new class of SIRT1 activators. The activation is dependent on the fluorophore labeled to the substrate. To elucidate the activation mechanism, we solved the crystal structure of SIRT3/ac-RHKKac-AMC complex. The structure revealed that the fluorophore blocked the H-bond formation and created a cavity between the substrate and the Rossmann fold. We built the SIRT1/ac-RHKK ac-AMC complex model based on the crystal structure. Km and Kd determinations demonstrated that the fluorophore decreased the peptide binding affinity. The binding modes of SIRT1 activators indicated that a portion of the activators interacts with the fluorophore through π-stacking, while the other portion inserts into the cavity or interacts with the Rossmann fold, thus increasing the substrate affinity. Our study provides new insights into the mechanism of SIRT1 activation and may aid the design of novel SIRT1 activators.

Discovering potent inhibitors against the β-hydroxyacyl-acyl carrier protein dehydratase (FabZ) of helicobacter pylori: Structure-based design, synthesis, bioassay, and crystal structure determination

The discovery of HpFabZ inhibitors is now of special interest in the treatment of various gastric diseases. In this work, three series of derivatives (compounds 3, 4, and 5) were designed, synthesized, and their biological activities were investigated as potential HpFabZ inhibitors in a two phased manner. First, we designed and synthesized two series of derivatives (3a-r and 4a-u) and evaluated the enzyme-based assay against HpFabZ. Five compounds (3i-k, 3m, and 3q) showed potential inhibitory activity, with IC50 values less than 2 μM. Second, a focused combinatorial library containing 280 molecules was designed employing the LD1.0 program. Twelve compounds (5a-l) were selected and synthesized. The activity of the most potent compound 5h (IC 50) 0.86 μM) was 46 times higher than that of the hit 1. The high hit rate and the potency of the new HpFabZ inhibitors demonstrated the efficiency of the strategy for the focused library design and virtual screening.

Two-photon uncaging with fluorescence reporting: Evaluation of the o-hydroxycinnamic platform

This paper evaluates the ohydroxycinnamic platform for designing efficient caging groups with fluorescence reporting upon one- and two-photon excitation. The model cinnamates are easily prepared in one step by coupling commercial or readily available synthons. They exhibit a large one-photon absorption that can be tuned in the near-UV range. Uncaging after one-photon excitation was investigated by 1H NMR, UV-vis absorption, and steady-state fluorescence emission. In the whole investigated series, the caged substrate is quantitatively released upon photolysis. At the same time, uncaging releases a strongly fluorescent coproduct that can be used as a reporter for quantitative substrate delivery. The quantum yield of double bond photoisomerization leading to uncaging after one-photon absorption mostly lies in the 10% range. Taking advantage of the favorable photophysical properties of the uncaging coproduct, we use a series of techniques based on fluorescence emission to measure the action uncaging cross sections with two-photon excitation of the present cinnamates. Exhibiting values in the 1-10 GM range at 750 nm, they satisfactorily compare with the most efficient caging groups reported to date. Noticeably, the uncaging behavior with two-photon excitation is retained in vivo as suggested by the results observed in living zebrafish embryos. Reliable structure property relationships were extracted from analysis of the present collected data. In particular, the careful kinetic analysis allows us to discuss the relevance of the ohydroxycinnamic platform for diverse caging applications with one- and two-photon excitation.

A convenient total synthesis of isofraxidin, a natural coumarin

The synthesis of isofraxidin in four steps starting from m-benzendiol, which is one of the important components of adrug in the treatment of insomnia, palpitation, amnesia and sexual deficiency in Chinese traditional medicine, is described.