126267-41-2

Upstream product

• 1450-74-4 5-chloro-2-hydroxyacetophenone 
• 104-88-1 4-chlorobenzaldehyde 

Downstream Products

• 111391-55-0 6-chloro-2-(4-chlorophenyl)-3-hydroxy-4H-chromen-4-one 
• 73110-56-2 4',6-dichloroflavan 
• 36768-56-6 6-chloro-2-(4-chlorophenyl)-4H-chromen-4-one 
• 78778-10-6 5-(5-chloro-2-hydroxy-phenyl)-7-(4-chloro-phenyl)-7,8-dihydro-3-methyl-6H-isoxazolo[4,5-b]azepine 
• 139006-35-2 (2S,3R)-6-Chloro-2-(4-chloro-phenyl)-4,4-dimethoxy-chroman-3-ol 
• 139006-43-2 (2R,3S)-6-Chloro-2-(4-chloro-phenyl)-3-hydroxy-chroman-4-one 
• 111391-74-3 6-Chloro-2-(4-chloro-phenyl)-3-methoxy-chromen-4-one 

Relevant academic research and scientific papers

Multitarget 2′-hydroxychalcones as potential drugs for the treatment of neurodegenerative disorders and their comorbidities

The complex nature of neurodegenerative diseases (NDDs), such as Alzheimer's disease (AD) and Parkinson's disease (PD) calls for multidirectional treatment. Restoring neurotransmitter levels by combined inhibition of cholinesterases (ChEs) and monoamine oxidases (MAOs, MAO-A and MAO-B), in conjunction with strategies to counteract amyloid β (Aβ) aggregation, may constitute a therapeutically strong multi-target approach for the treatment of NDDs. Chalcones are a subgroup of flavonoids with a broad spectrum of biological activity. We report here the synthesis of 2′-hydroxychalcones as MAO-A and MAO-B inhibitors. Compounds 5c (IC50 = 0.031 ± 0.001 μM), 5a (IC50 = 0.084 ± 0.003 μM), 2c (IC50 = 0.095 ± 0.019 μM) and 2a (IC50 = 0.111 ± 0.006 μM) were the most potent, selective and reversible inhibitors of human (h)MAO-B isoform. hMAO-B inhibitors 1a, 2a and 5a also inhibited murine MAO-B in vivo in mouse brain homogenates. Molecular modelling rationalised the binding mode of 2′-hydroxychalcones in the active site of hMAO-B. Additionally, several derivatives inhibited murine acetylcholinesterase (mAChE) (IC50 values from 4.37 ± 0.83 μM to 15.17 ± 6.03 μM) and reduced the aggregation propensity of Aβ. Moreover, some derivatives bound to the benzodiazepine binding site (BDZ-bs) of the γ-aminobutyric acid A (GABAA) receptors (1a and 2a with Ki = 4.9 ± 1.1 μM and 5.0 ± 1.1 μM, respectively), and exerted sedative and/or anxiolytic like effects on mice. The biological results reported here on 2′-hydroxychalcones provide an extension to previous studies on chalcone scaffold and show them as a potential treatment strategy for NDDs and their associated comorbidities.

Synthesis and biological activities of some flavones

Chalcones are synthesized by a base catalyzed Claisen Schmidt condensation reaction and then treated with dimethylsulphoxide in presence of iodine to get flavones. The synthesized compounds were evaluated for their antibacterial activity against Escherichia coilt P. aeruginosa, S. epidermidis and B. subtilis. All the flavones showed moderate to good activity. The structures of these compounds were confirmed by IR, UV, 1H NMR, Mass and elemental analysis.

Biological evaluation of synthetic analogues of curcumin: Chloro-substituted-20-hydroxychalcones as potential inhibitors of tubulin polymerization and cell proliferation

A series of chloro-substituted-20-hydroxychalcones were prepared and evaluated for their cytotoxic effects against K562 and SK-N-MC human cancer cell lines and as the inhibitors of tubulin polymerization. The 3,50-dichloro- analogue (compound 3) inhibited the assembly of protofilaments with 89% inhibition. Compound 3 was found to be bound to tubulin with a dissociation constant of 3.7 lM and altered far-UV circular dichroism spectrum of tubulin and altered far-UV circular dichroism spectrum of tubulin.

Synthesis and fungicidal evaluation of novel chalcone-based strobilurin analogues

Strobilurin derivatives have become one of the most important classes of agricultural fungicide due to a novel action mode, wide fungicidal spectrum, lower toxicity toward mammalian cells, and environmentally benign characteristics. To discover new strobilurin analogues with high activity against resistant pathogens, a series of new chalcone-based strobilurin derivatives are designed and synthesized by integrating a chalcone scaffold with a strobilurin pharmacophore. The preliminary bioassay showed that some of the chalcone analogues exhibited good in vivo fungicidal activities against Pseudoperoniospora cubensis and Sphaerotheca fuliginea at the dosage of 200 μg mL-1. Two compounds, (￡)-methyl 2-[2-({3-[(￡)-3-(2- chlorophenyl)acryloyl]phenoxy}methyl)phenyl]-3-meth-oxyacrylate (1e) and (E)-methyl 2-[2-({3-[(E)-3-(3-bromophenyl)acryloyl]phenoxy}methyl)phenyl]-3- methoxyacrylate (11), were found to display higher fungicidal activities against P. cubensis (EC90 = 118.52 μg ml-1 for 1e and EC 90 = 113.64 μg mL-1 for 11) than Kresoxim-methyl (EC90 = 154.92 μg mL-1) and were identified as the most promising candidates for further study. The present work demonstrated that strobilurin analogues containing chalcone as a side chain could be used as a lead structure for further developing novel fungicides. To our knowledge, this is the first report about the syntheses and fungicidal activities of chalcone-based strobilurin derivatives.

Inhibitory effects of 2'-hydroxychalcones on rat lens aldose reductase and rat platelet aggregation

Inhibitory effects of synthetic 2'-hydroxychalcone derivatives on rat lens aldose reductase (RLAR) and on platelet aggregation were investigated for the prevention or the treatment of chronic diabetic complications. 5'-chloro-4,2'-dihydroxychalcone (8) and 5'-chloro-3,2'-dihydroxychalcone (27) exhibited a potent inhibitory effect on rat platelet aggregation induced by ADP (IC50=0.10 and 0.06 mg/ml, respectively) and collagen (IC50=44 and 16 μg/ml, respectively) but showed relatively weak inhibitory activities on RLAR.

4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5 μg/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.