116096-90-3

Upstream product

• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 557-21-1 zinc(II) cyanide 
• 6626-15-9 4-Bromoresorcinol 
• 130333-46-9 5-bromo-2, 4-dimethoxybenzaldehyde 

Downstream Products

• 51061-83-7 2,4-dihydroxy-5-methoxybenzaldehyde 
• 1227484-18-5 5-bromo-2-hydroxy-4-(methoxymethoxy)benzaldehyde 
• 1372864-94-2 5-(5-bromo-2,4-dihydroxybenzylidene)-3-(2-ethylbutyl)thiazolidine-2,4-dione 
• 1421925-14-5 C₂₄H₂₄BrNO₅ 
• 1421925-16-7 C₂₃H₂₃BrN₂O₅ 
• 1421925-18-9 C₂₄H₂₅BrN₂O₆ 
• 1620146-74-8 5-bromo-4-butoxy-2-methoxybenzaldehyde 
• 1620146-75-9 4-(benzyloxy)-5-bromo-2-methoxybenzaldehyde 
• 1620146-39-5 (Z)-5-(5-bromo-4-hydroxy-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-40-8 (Z)-5-(5-bromo-2, 4-dimethoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-41-9 (Z)-5-(5-bromo-4-(allyloxy)-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-42-0 (Z)-5-(5-bromo-4-((3-methylbut-2-en-1-yl)oxy)-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-43-1 (Z)-5-(5-bromo-4-butoxy-2-methoxybenzylidene)thiazolidine-2,4-dione 
• 1620146-44-2 (Z)-5-(5-bromo-4-benzyloxy-2-methoxybenzylidene)thiazolidine-2,4-dione 

Relevant academic research and scientific papers

Novel coumarin-based fluorescent probe for selective detection of bisulfite anion in water

Coumarins and its analogues have been widely used as chromophore in design of fluorescent probe, while less coumarin-based fluorescent probe was reported for detection of anion in water. In this article, coumarin-based fluorescent probes with salicylaldehyde functionality as recognition unit have been developed for selective detection of bisulfite anions in water. Four novel fluorescent probes were synthesized from 4-haloresorcinol in three steps. The chemoprobe exhibited selective response to bisulfite over other anions. Moreover, the detection mechanism was studied. Upon bisulfite added, the fluorescent intensity of the probes was enhanced highly due to the nucleophilic addition reaction of formyl group with bisulfite anion.

Design, synthesis, and biological evaluation of coumarin analogs as novel LSD1 inhibitors

The abnormal expression of lysine-specific histone demethylase 1 (LSD1) is associated with different cancer types, and it is increasingly recognized as a potential therapeutic target in oncology. Here, utilizing core hopping and conformational restriction strategies, we designed and synthesized a series of coumarin analogs that were shown to be potent LSD1 inhibitors in the enzyme assay. Furthermore, several potent compounds were selected to evaluate their antiproliferative activity on A549 cells and MGC-803 cells with high expression of LSD1. Among them, YX10 showed an anticlonogenic effect on A549 cells and MGC-803 cells, with IC50 values of 1.52 ± 0.16 and 0.98 ± 0.18 μM, respectively. Modeling suggested that the inhibitors would bind to the active site of the protein located around the key residues of Asp555 and Lys661. Meanwhile, a preliminary druggability evaluation showed that compound YX10 showed favorable liver microsomal and moderate plasma stability and weak inhibitory activity against cytochrome P450 isoforms at 10 μM. All the results indicated that compound YX10 could represent a promising lead compound for further development.

Structure-Activity Relationship Studies of Coumarin-like Diacid Derivatives as Human G Protein-Coupled Receptor-35 (hGPR35) Agonists and a Consequent New Design Principle

A series of coumarin-like diacid derivatives were designed and synthesized as novel agonists of human G-protein-coupled receptor 35 (hGPR35). Active compounds were characterized to possess one acidic group on both sides of a fused tricyclic aromatic scaff

Synthetic route of compound and application thereof in field of preparation of anti-diabetic drugs

The invention belongs to the technical field of drug synthesis, and particularly relates to a synthetic route of a compound and application of the compound in the field of preparation of anti-diabeticdrugs. The invention provides a synthetic route of SN158, and also provides the application of the synthetic route in the field of preparation of anti-diabetic drugs. The synthetic route of the invention comprises the following steps: brominating a raw material, namely 2,4-dihydroxybenzaldehyde; protecting para-hydroxyl groups by using methoxymethyl groups; methylating ortho-hydroxyl groups by using dimethyl sulfate or methyl iodide; and carrying out a Claisen-Schmidt condensation reaction by using a hydrochloric acid ethanol or boron trifluoride diethyl ether solution, with HATU or EDCI andHOBt as coupling agents for an amidation reaction. According to the invention, the yield of the prepared SN158 can reach 60% or above; meanwhile, column chromatographic purification is not needed in the preparation process, and the finally produced compound with a purity of 99% or above can be obtained only through recrystallization; and the method is suitable for large-scale/industrial productionand overcomes the technical defects that SN158 is low in synthesis yield and complex in purification in the prior art.

Biphenyl compound as well as preparation method and medical application thereof

The invention discloses a biphenyl compound as well as a preparation method and medical application thereof, the structure of the biphenyl compound is shown as a formula (I) or a formula (II), and thebiphenyl compound or pharmaceutically acceptable salt, tautomer, meso-isomer, raceme, stereoisomer, metabolite, metabolite precursor, prodrug or solvate thereof is a PD-L1 inhibitor. The compound hasa remarkable inhibiting effect on the interaction of PD-1 and PD-L1 protein, so that the compound can be applied to the preparation of PD-L1 inhibitors and immunomodulator drugs for preventing or treating tumors, autoimmune diseases, organ transplant rejection, infectious diseases and inflammatory diseases.

Synthesis method for compound and application thereof in field of medicines used for improving insulin resistance

The invention belongs to the technical field of drug synthesis, and particularly relates to a synthesis method for a compound and application thereof in field of medicines used for improving insulin resistance. The invention provides the synthesis method of SN159. The synthesis method comprises the following steps: brominating a raw material, namely 2,4-dihydroxy benzaldehyde, protecting para-hydroxyl groups by using methoxymethyl groups, performing methylating by using dimethyl sulfate or methyl iodide, and carrying out a Claisen-Schmidt condensation reaction under an alkaline or acidic condition, thereby enhancing the yield of the finally produced compound from 18.9% in the prior art to 68% or above. According to the invention, column chromatographic purification is not needed in the preparation process, and the finally produced compound with a purity of 99% or above can be obtained only through recrystallization; and the method is suitable for large-scale/industrial production. According to the synthesis method of the compound and the application of the compound in the field of preparation of medicines used for improving insulin resistance, the technical defects that SN159 is low in synthesis yield and complex in purification in the prior art are overcome.

Coumarin derivative capable of serving as GPR35 receptor stimulant and preparation method and application thereof

The invention provides a coumarin derivative capable of serving as a GPR35 receptor stimulant, a preparation method and application thereof. The activity of the series of compounds on a human GPR35 receptor is tested by acting the compounds on the human G

Competitive Binding Assay with an Umbelliferone-Based Fluorescent Rexinoid for Retinoid X Receptor Ligand Screening

Ligands for retinoid X receptors (RXRs), "rexinoids", are attracting interest as candidates for therapy of type 2 diabetes and Alzheimer's and Parkinson's diseases. However, current screening methods for rexinoids are slow and require special apparatus or facilities. Here, we created 7-hydroxy-2-oxo-6-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-2H-chromene-3-carboxylic acid (10, CU-6PMN) as a new fluorescent RXR agonist and developed a screening system of rexinoids using 10. Compound 10 was designed based on the fact that umbelliferone emits strong fluorescence in a hydrophilic environment, but the fluorescence intensity decreases in hydrophobic environments such as the interior of proteins. The developed assay using 10 enabled screening of rexinoids to be performed easily within a few hours by monitoring changes of fluorescence intensity with widely available fluorescence microplate readers, without the need for processes such as filtration.

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.