24589-99-9

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 3-FORMYL-4-HYDROXYBENZOATE is used as a synthetic intermediate for the production of 1,2-Benzisoxazole-5-carboxylic Acid (B197900), a compound with potential applications in the development of new drugs.
METHYL 3-FORMYL-4-HYDROXYBENZOATE is also used as a synthetic intermediate in the synthesis of Roflumilast (R639700), a selective phosphodiesterase 4 (PDE4) inhibitor. Roflumilast is an antiasthmatic drug used in the treatment of chronic obstructive pulmonary disease (COPD), helping to improve lung function and reduce inflammation.

InChI:InChI=1/C9H8O4/c1-13-9(12)6-2-3-8(11)7(4-6)5-10/h2-5,11H,1H3

Upstream product

• 67-56-1 methanol 
• 584-87-2 3-formyl-4-hydroxybenzoic acid 
• 100-97-0 hexamethylenetetramine 
• 99-76-3 methyl 4-hydroxylbenzoate 
• 50-00-0 formaldehyd 
• 52178-50-4 Methyl 3-formylbenzoate 
• 59648-31-6 4-hydroxy-3-hydroxymethylbenzoic acid methyl ester 
• 140-88-5 ethyl acrylate 
• 76-05-1 trifluoroacetic acid 
• 99-96-7 4-hydroxy-benzoic acid 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 74-88-4 methyl iodide 
• 108-43-0 3-monochlorophenol 

Downstream Products

• 90334-75-1 3-{[(E)-4-Chloro-phenylimino]-methyl}-4-hydroxy-benzoic acid methyl ester 
• 90334-78-4 4-Hydroxy-3-{[(E)-4-nitro-phenylimino]-methyl}-benzoic acid methyl ester 
• 90334-76-2 3-{[(E)-4-Bromo-phenylimino]-methyl}-4-hydroxy-benzoic acid methyl ester 
• 90334-77-3 4-Hydroxy-3-{[(E)-4-iodo-phenylimino]-methyl}-benzoic acid methyl ester 
• 163163-68-6 methyl 3-formyl-4-<(2-chloroethyl)oxy>benzoate 
• 706820-79-3 methyl 3-bromo-5-formyl-4-hydroxybenzoate 
• 947232-28-2 methyl 4-(tert-butyldimethylsilyloxy)-3-formyl-benzoate 
• 706820-85-1 methyl 3-bromo-5-formyl-4-(2-methoxyethoxymethoxy)-benzoate 
• 145742-55-8 methyl 3-formyl-4-methoxybenzoate 
• 1224447-24-8 C₁₈H₁₄O₈ 
• 1256841-99-2 C₁₉H₁₈O₄ 
• 1256842-00-8 C₁₉H₁₈O₄ 
• 1256168-93-0 methyl 4-hydroxy-3-(2-methyl-4-(phenylthio)butanoyl)benzoate 

Relevant academic research and scientific papers

Redox supramolecular self-assemblies nonlinearly enhance fluorescence to identify cancer cells

Based on the nonlinear fluorescence enhancement, our H2O2 induced supramolecular self-assembly reveals a H2O2 threshold among multiple cancer and normal cells. Oxidative elimination restores an intramolecular hy

A novel synthesis of polysubstituted chromenes from various salicylaldehydes and alkynes under mild conditions

A novel synthesis of poly substituted chromenes from various salicylaldehydes and alkynes not having electron withdrawing substituents under mild conditions has been developed. The procedure is applicable for easily available various substituted salicylal

Photocaged Quinone Methide Crosslinkers for Light-Controlled Chemical Crosslinking of Protein–Protein and Protein–DNA Complexes

Small-molecule crosslinkers are invaluable for probing biomolecular interactions and for crosslinking mass spectrometry. Existing chemical crosslinkers target only a small selection of amino acids, while conventional photo-crosslinkers target almost all r

Demonstrating Ligandability of the LC3A and LC3B Adapter Interface

Autophagy is the common name for a number of lysosome-based degradation pathways of cytosolic cargos. The key components of autophagy are members of Atg8 family proteins involved in almost all steps of the process, from autophagosome formation to their selective fusion with lysosomes. In this study, we show that the homologous members of the human Atg8 family proteins, LC3A and LC3B, are druggable by a small molecule inhibitor novobiocin. Structure-activity relationship (SAR) studies of the 4-hydroxy coumarin core scaffold were performed, supported by a crystal structure of the LC3A dihydronovobiocin complex. The study reports the first nonpeptide inhibitors for these protein interaction targets and will lay the foundation for the development of more potent chemical probes for the Atg8 protein family which may also find applications for the development of autophagy-mediated degraders (AUTACs).

Phosphine-catalyzed sequential (2+3)/(2+4) annulation of γ-vinyl allenoates: Access to the synthesis of chromeno[4,3-: B] pyrroles

A phosphine-catalyzed cascade (2+3)/(2+4) cyclization reaction of γ-vinyl allenoates with aldimine esters has been developed to provide a series of chromeno[4,3-b]pyrrole derivatives that contain three contiguous stereogenic centers. The method gives a good yield, excellent chemoselectivity and diastereoselectivity under mild conditions.

Boron-containing small molecule compound, and preparation method and application thereof

The invention discloses a novel compound with an anti-tumor effect as shown in a formula I, and a preparation method and application thereof. NOD-SCID mouse transplanted tumor model experiments show that the compounds can inhibit tumor growth. Further res

Biosynthesis of Biscognienyne B Involving a Cytochrome P450-Dependent Alkynylation

The alkyne is a biologically significant moiety found in many natural products and a versatile functional group widely used in modern chemistry. Recent studies have revealed the biosynthesis of acetylenic bonds in fatty acids and amino acids. However, the

Design, synthesis, and biological evaluation of dual targeting inhibitors of histone deacetylase 6/8 and bromodomain BRPF1

Histone modifying proteins, specifically histone deacetylases (HDACs) and bromodomains, have emerged as novel promising targets for anticancer therapy. In the current work, based on available crystal structures and docking studies, we designed dual inhibitors of both HDAC6/8 and the bromodomain and PHD finger containing protein 1 (BRPF1). Biochemical and biophysical tests showed that compounds 23a,b and 37 are nanomolar inhibitors of both target proteins. Detailed structure-activity relationships were deduced for the synthesized inhibitors which were supported by extensive docking and molecular dynamics studies. Cellular testing in acute myeloid leukemia (AML) cells showed only a weak effect, most probably because of the poor permeability of the inhibitors. We also aimed to analyse the target engagement and the cellular activity of the novel inhibitors by determining the protein acetylation levels in cells by western blotting (tubulin vs histone acetylation), and by assessing their effects on various cancer cell lines.

Novel, Self-Assembling Dimeric Inhibitors of Human β Tryptase

β-Tryptase, a homotetrameric serine protease, has four identical active sites facing a central pore, presenting an optimized setting for the rational design of bivalent inhibitors that bridge two adjacent sites. Using diol, hydroxymethyl phenols or benzoyl methyl hydroxamates, and boronic acid chemistries to reversibly join two [3-(1-acylpiperidin-4-yl)phenyl]methanamine core ligands, we have successfully produced a series of self-assembling heterodimeric inhibitors. These heterodimeric tryptase inhibitors demonstrate superior activity compared to monomeric modes of inhibition. X-ray crystallography validated the dimeric mechanism of inhibition, and compounds demonstrated high selectivity against related proteases, good target engagement, and tryptase inhibition in HMC1 xenograft models. Screening 3872 possible combinations from 44 boronic acid and 88 diol derivatives revealed several combinations that produced nanomolar inhibition, and seven unique pairs produced greater than 100-fold improvement in potency over monomeric inhibition. These heterodimeric tryptase inhibitors demonstrate the power of target-driven combinatorial chemistry to deliver bivalent drugs in a small molecule form.

Design, synthesis and biological evaluation of antimicrobial diarylimine and –amine compounds targeting the interaction between the bacterial NusB and NusE proteins

Discovery of antimicrobial agents with a novel model of action is in urgent need for the clinical management of multidrug-resistant bacterial infections. Recently, we reported the identification of a first-in-class bacterial ribosomal RNA synthesis inhibitor, which interrupted the interaction between the bacterial transcription factor NusB and NusE. In this study, a series of diaryl derivatives were rationally designed and synthesized based on the previously established pharmacophore model. Inhibitory activity against the NusB-NusE binding, circular dichroism of compound treated NusB, antimicrobial activity, cytotoxicity, hemolytic property and cell permeability using Caco-2 cells were measured. Structure-activity relationship and quantitative structure–activity relationship were also concluded and discussed. Some of the derivatives demonstrated improved antimicrobial activity than the hit compound against a panel of clinically important pathogens, lowering the minimum inhibition concentration to 1–2 μg/mL against Staphylococcus aureus, including clinical strains of methicillin-resistant Staphylococcus aureus at a level comparable to some of the marketed antibiotics. Given the improved antimicrobial activity, specific inhibition of target protein-protein interaction and promising pharmacokinetic properties without significant cytotoxicity, this series of diaryl compounds have high potentials and deserve for further studies towards a new class of antimicrobial agents in the future.