27164-10-9

Usage

Uses

Used in Pharmaceutical Industry:
2,5-Dichloro-4-hydroxy-benzaldehyde is used as a key intermediate in the design and preparation of gut-restricted thiazolidine agonists of G protein-coupled bile acid receptor 1 (GPBAR1, TGR5). These agonists have potential applications in treating various metabolic disorders and improving overall health.
Used in Psychotropic Agents:
In the field of psychopharmacology, 2,5-dichloro-4-hydroxy-benzaldehyde is utilized in the synthesis of new mescaline analogs. These analogs are being investigated for their potential as psychotropic agents, which could be used in the treatment of certain psychiatric conditions or for research purposes.
Used in Immunology and Cell Adhesion:
2,5-Dichloro-4-hydroxy-benzaldehyde is also used in the discovery of novel p-arylthio cinnamides. These compounds act as antagonists of leukocyte function-associated antigen-1 (LFA-1) and intercellular adhesion molecule-1 (ICAM-1). By targeting these molecules, p-arylthio cinnamides may have applications in modulating immune responses and reducing cell adhesion-related issues in various diseases.

InChI:InChI=1/C7H4Cl2O2/c8-5-2-7(11)6(9)1-4(5)3-10/h1-3,11H

Upstream product

• 67-66-3 chloroform 
• 583-78-8 2,5-dichlorophenol 
• 1984-58-3 2,5-dichloroanisole 
• 381229-74-9 4-methoxy-3,6-dichlorobenzaldehyde 

Downstream Products

• 1445985-45-4 tert-butyl N-[3-(2,5-dichloro-4-formylphenyl)prop-2-yn-1-yl]carbamate 
• 1445985-46-5 tert-butyl N-[3-(2,5-dichloro-4-formylphenyl)propyl]carbamate 
• 1445985-98-7 C₁₅H₂₁Cl₂NO₃ 
• 1445985-99-8 C₁₅H₂₀BrCl₂NO₂ 
• 1445985-49-8 tert-butyl 5-(2,5-dichioro-4-formylphenyl)pent-4-ynylcarbamate 
• 1445985-50-1 tert-butyl 5-(2,5-dichloro-4-formylphenyl)pentylcarbamate 
• 1445985-51-2 tert-butyl 5-(2,5-dichloro-4-(hydroxymethyl)phenyl)pentylcarbamate 
• 1445985-52-3 tert-butyl 5-(4-(bromomethyl)-2,5-dichlorophenyl)pentylcarbamate 
• 1445985-53-4 (R)-tert-butyl 5-(2,5-dichloro-4-((4-(4-cyclopropyl-1,2,3,4-tetrahydroquinoxaline-1-carbonyl)thiazolidin-3-yl)methyl)phenyl)pentylcarbamate 
• 1445983-25-4 (R)-(3-(4-(5-aminopentyl)-2,5-dichlorobenzyl)thiazolidin-4-yl)(4-cyclopropyl-3,4-dihydroquinoxalin-1(2H)-yl)methanone 
• 1445985-55-6 methyl 5-(2,5-dichloro-4-formylphenyl)pent-4-ynoate 
• 1445985-56-7 methyl 5-(2,5-dichloro-4-formylphenyl)pentanoate 
• 1445985-57-8 methyl 5-(2,5-dichloro-4-(hydroxymethyl)phenyl)pentanoate 
• 1445985-58-9 methyl 5-(4-(bromomethyl)-2,5-dichlorophenyl)pentanoate 

Relevant academic research and scientific papers

Design of Gut-Restricted Thiazolidine Agonists of G Protein-Coupled Bile Acid Receptor 1 (GPBAR1, TGR5)

Bile acid signaling and metabolism in the gastrointestinal tract have wide-ranging influences on systemic disease. G protein-coupled bile acid receptor 1 (GPBAR1, TGR5) is one of the major effectors in bile acid sensing, with demonstrated influence on metabolic, inflammatory, and proliferative processes. The pharmacologic utility of TGR5 agonists has been limited by systemic target-related effects such as excessive gallbladder filling and blockade of gallbladder emptying. Gut-restricted TGR5 agonists, however, have the potential to avoid these side effects and consequently be developed into drugs with acceptable safety profiles. We describe the discovery and optimization of a series of gut-restricted TGR5 agonists that elicit a potent response in mice, with minimal gallbladder-related effects. The series includes 12 (TGR5 EC50: human, 143 nM; mouse, 1.2 nM), a compound with minimal systemic availability that may have therapeutic value to patients with type 2 diabetes mellitus, nonalcoholic steatohepatitis, or inflammatory bowel disease.

NON-SYSTEMIC TGR5 AGONISTS

Compounds of structure (I), or a stereoisomer, tautomer, pharmaceutically acceptable salt or prodrug thereof, wherein R1, R2, R3, R4, R8, R9, R10, R11, R12, A1, A2, X, Y and Z are as defined herein. Uses of such compounds as TGR5 antagonists and for treatment of various indications, including Type II diabetes meletus are also provided.

Discovery of novel p-arylthio cinnamides as antagonists of leukocyte function-associated antigen-1/intercellular adhesion molecule-1 interaction. 4. Structure - Activity relationship of substituents on the benzene ring of the cinnamide

We have shown that p-arylthio cinnamides can inhibit the interaction of LFA-1 and ICAM-1, which is involved in cell adhesion and the inflammatory process. We now show that 2,3-disubstitution on the aryl portion of the cinnamide results in enhanced activit

Synthesis and Spectroscopic Data of Chlorinated 4-Hydroxybenzaldehydes

All chlorinated 4-hydroxybenzaldehydes including three hitherto unknown compounds have been synthesized from chlorinated phenols by applying the Reimer-Tiemann method. (1)H NMR, (13)C NMR, and mass-spectral data on all compounds are reported.