75808-79-6

Upstream product

• 26506-02-5 4-Methoxy-benzoic acid 2-acetyl-3-hydroxy-phenyl ester 
• 76937-63-8 1-(4-Benzyloxy-2-hydroxy-phenyl)-3-(4-methoxy-phenyl)-propane-1,3-dione 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 100-07-2 4-methoxy-benzoyl chloride 
• 29682-12-0 1-[4-(benzyloxy)-2-hydroxyphenyl]ethanone 
• 5706-85-4 2-hydroxy-1-(4-hydroxyphenyl)ethan-1-one 
• 121-98-2 methyl 4-methoxybenzoate 
• 100-09-4 4-methoxybenzoic acid 
• 67881-34-9 2',4'-bis(4-methoxybenzoyloxy)acetophenone 

Downstream Products

• 115123-03-0 1-(4'-β-D-glucopyranosyloxy-2'-hydroxyphenyl)-3-(4''-methoxyphenyl)-propane-1,3-dione 
• 1489101-77-0 7-(3-bromopropoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 10400-05-2 7-(2-(dimethylamino)ethoxy)-2-(4-methoxyphenyl)-4H-chromen-4-one 
• 487-24-1 pratol 

Relevant academic research and scientific papers

Identification of inhibitors targeting polyketide synthase 13 of Mycobacterium tuberculosis as antituberculosis drug leads

Polyketide synthase 13 (Pks13) is an essential enzyme in the synthesis of mycolic acids in Mtb. Therefore, Pks13 is a promising drug target for tuberculosis treatment. We used a structure-guided approach to identify novel chemotype inhibitors of Pks13 and assessed them using a Pks13 enzymatic assay and surface plasmon resonance. The structure–activity relationships (SAR) results demonstrated that the substituents at the 2, 5, and 6 positions of the 4H-chromen-4-one scaffold are critical for maintaining the MIC. Compound 6e with 2-hydroxyphenyl at the 2 position of the 4H-chromen-4-one scaffold, exhibited potent activity against Mtb H37Rv (MIC = 0.45 μg/mL) and displayed good Pks13 affinity and inhibition (IC50 = 14.3 μM). This study described here could provide an avenue to explore a novel inhibitor class for Pks13 and aid the further development of antituberculosis drugs.

Design, synthesis and biological evaluation of 2-Phenyl-4H-chromen-4-one derivatives as polyfunctional compounds against Alzheimer’s disease

Polyfunctional compounds comprise a novel class of therapeutic agents for the treatment of multi-factorial diseases. A series of 2-Phenyl-4H-chromen-4-one and its derivatives (5a–n) were designed, synthesized, and evaluated for their poly-functionality against acetylcholinestrase (AChE) and advanced glycation end products (AGEs) formation inhibitors against Alzheimer’s disease (AD). The screening results showed that most of them exhibited a significant ability to inhibit AChE AGEs formation with additional radical scavenging activity. Especially, 5m, 5b, and 5j displayed the greatest ability to inhibit AChE (IC50 = 8.0, 8.2, and 11.8 nM, respectively) and AGEs formation (IC50 = 55, 79, and 54 μM, respectively) with good antioxidant activity. Molecular docking studies explored the detailed interaction pattern with active, peripheral, and mid-gorge sites of AChE. These compounds, exhibiting such multiple pharmacological activities, can be further taken a lead for the development of potent drugs for the treatment of Alzheimer’s disease.

Exploration of multi-target potential of chromen-4-one based compounds in Alzheimer's disease: Design, synthesis and biological evaluations

A novel series of flavonoid based compounds were designed, synthesized and biologically evaluated for Acetylcholinesterase (AChE) inhibitory activity integrated with advanced glycation end products (AGEs) inhibitory and antioxidant potential. Most of the derivatives inhibited AChE in nanomolar IC50 range along with good AGEs inhibitory and radical scavenging activity. Among them, 7m, strongly inhibited AChE (IC50 = 5.87 nM) and found to be potent as compared to the reference drug donepezil (IC50 = 12.7 nM). Its potent inhibitory activity has been justified by docking analysis that revealed its dual binding characteristic with both CAS (catalytic active site) and PAS (peripheral anionic site) of AChE, simultaneously. Additionally, this compound also displayed ability to prevent advanced glycation end products formation (IC50 = 23.0 μM) with additional radical scavenging property (IC50 = 37.12 nM). It (7m) also ameliorated scopolamine induced memory deficit in mice employing Morris water maze test. Thus, flavonoids might be the promising lead compounds as potential polyfunctional anti-Alzheimer's agents.

Design, synthesis and biological evaluation of novel 2-phenyl-1-benzopyran-4-one derivatives as potential poly-functional anti-Alzheimer's agents

The development of Multi-Target Directed Ligands (MTDLs) has emerged as a promising approach for targeting the complex etiology of Alzheimer's disease (AD). Following this approach, a new series of 2-phenyl-1-benzopyran-4-one derivatives was designed, synthesized and biologically evaluated as inhibitors of acetylcholinesterases (AChEs), advanced glycation end product (AGEs) formation and also for their radical scavenging activity. The in vitro studies showed that the majority of the synthesized derivatives inhibited acetylcholinesterase (AChE) with IC50 values in the low-micromolar range. Among them, inhibitors 7a, 7h and 7k, strongly inhibited AChE, with IC50 values of 6.33, 7.56 and 11.0 nM, respectively, and were more potent than the reference compound donepezil. Moreover, the molecular docking study showed that most potent compounds simultaneously bind to the catalytic active site and the peripheral anionic site of AChE. Additionally, these compounds exhibited a greater ability to inhibit advanced glycation end product formation with additional radical scavenging properties. Thus, 2-phenyl-1-benzopyran-4-one derivatives might be promising lead compounds for potential poly-functional anti-Alzheimer's agents.

Synthesis, biopharmaceutical characterization, antimicrobial and antioxidant activities of 1-(4′-O-β-d-glucopyranosyloxy-2′- hydroxyphenyl)-3-aryl-propane-1,3-diones

This research communication is toward the investigation of the antibacterial, antifungal and antioxidant activities of the synthesized compounds 1-(4′-O-β-d-glucopyranosyloxy-2′-hydroxyphenyl)-3- aryl-propane-1,3-diones (5a)-(5h). These compounds have bee

A rational approach to the design of flavones as xanthine oxidase inhibitors

In the light of previous QSAR studies on flavones as inhibitors of xanthine oxidase, we synthesized and tested a new series of 7-hydroxyflavones carrying a wide and balanced variety of substituents (π, σ(p)) at the 4' position in order to explore the effect of substituents at this position on the xanthine oxidase inhibitory activity. The results of pK(a) determinations show that the electronic effects of the substituents are not transferred to the hydroxyl at C7, previously found to be fundamental for activity. An excellent correlation is found between molar refractivity of the substituents and the inhibitory activity. These results, applied to the more active 5,7-dihydroxyflavones, allowed the design and synthesis of a very active inhibitor, with an IC50 in the nanomolar range. On interpretative grounds, C4' substituents of flavones are involved in dispersion interactions with the enzyme. The calculation of quantum chemical polarizabilities and solvent accessible surface areas suggests the existence of π-π stacking interactions with an aromatic aminoacidic residue of the enzyme.

BIOSYNTHESIS OF A RETROCHALCONE ECHINATIN: INVOLVEMENT OF O-METHYLTRANSFERASE TO LICODIONE

In order to clarify the O-methylation step in the bisynthesis of a retrochalcone, echinatin (4,4'-dihydroxy-2-methoxychalcone), methyl transfer from S-adenosyl-L-methionine (SAM) to licodione (1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-1,3-propanedione) in the cell-free extract of the cultured cells of Glycyrrhiza echinata was examined.Time course of methyl transferring activity during culture cycle in 4 strains was correlated to echinatin content.The enzyme catalysing this reaction, licodione O-methyltransferase (LMT), was purified 135-fold.Substrate specificity studies implied that the hydroxy group ortho to the C3 linkage in licodione was methylated in this reaction.O-Methyl-licodiones were synthesized for comparison and the sole product of LMT-catalysed reaction was identified as 2'-O-methyl-licodione.A possible scheme for the last steps of echinatin biosynthesis is proposed. - Key Word Index: Glycyrrhiza echinata; Leguminosae; cell culture; cell free extract; retrochalcone biosynthesis; enzyme; O-methyltransferase; echinatin; licodione; O-methyl-licodiones.