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Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 1311272-33-9 2'-hydroxy-5'-(methoxymethoxy)-4-methoxychalcone 
• 1026975-99-4 (E)-1-[2,5-Bis-(tetrahydro-pyran-2-yloxy)-phenyl]-3-(4-methoxy-phenyl)-propenone 
• 204703-68-4 2',5'-bis(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)acetophenone 

Downstream Products

• 1250377-74-2 1-[1-(2,5-dihydroxyphenyl)-3-(4-methoxyphenyl)allylidene]-4-(2-fluorophenyl)semicarbazide 
• 1210039-52-3 1-[1-(2,5-dihydroxyphenyl)-3-(4-methoxyphenyl)allylidene]-4-(4-bromophenyl)semicarbazide 
• 1210039-62-5 1-[1-(2,5-dihydroxyphenyl)-3-(4-methoxyphenyl)allylidene]-4-(4-fluorophenyl)semicarbazide 
• 3557-24-2 6-hydroxy-4'-methoxyflavanone 

Relevant academic research and scientific papers

Synthesis and biological evaluations of chalcones, flavones and chromenes as farnesoid x receptor (FXR) antagonists

Farnesoid X receptor (FXR), a nuclear receptor mainly distributed in liver and intestine, has been regarded as a potential target for the treatment of various metabolic diseases, cancer and infectious diseases related to liver. Starting from two previously identified chalcone-based FXR antagonists, we tried to increase the activity through the design and synthesis of a library containing chalcones, flavones and chromenes, based on substitution manipulation and conformation (ring closure) restriction strategy. Many chalcones and four chromenes were identified as microM potent FXR antagonists, among which chromene 11c significantly decreased the plasma and hepatic triglyceride level in KKay mice.

Synthesis and pharmacological screening of some novel chalconyl derivatives of substituted phenyl semicarbazide

In the present study, we have synthesized chalcone and semicarbazide-linked chalonyl derivatives and the titled compounds confirmed by MS, IR, and 1H NMR techniques. The anticonvulsant activity was determined by maximal electroshock (MES) induced seizure method. A majority of the compounds exhibited significant anticonvulsant activity after intraperitoneal administration. The results show the importance of hydrogen bonding for activity. In the present study 5e, 5h, 5i, 6e, 6h, and 6i emerged as the most active molecules, showed significant anticonvulsant of activity. Springer Science+Business Media, LLC 2010.

Chalconsemicarbazone: A new scaffold for antiepileptic drug discovery

During our investigation in the area of epileptic drug discovery, we have identified that the available conventional antiepileptic drugs are effective in 60-80% patients and in specific type of seizures and having various undesirable side effects. But in present time a new class aryl semicarbazone is emerged as new pharmacophore in epileptic drug discovery having broad spectrum activity. On the bases of work done in this area we have applied hybridization of pharmacophore strategy of drug design and developed a new pharmacophore. We have also designed a scheme for synthesizing such pharmacophore and performed their pharmacological screening for the protection of seizures, behavioral study and CNS activity. The compound 1-[1-(2,4-dihydroxyphenyl)-3-(2-hydroxyphenyl) allylidene]-4-(2-fluorophenyl) semicarbazide (8) emerged as the most active prototype molecule in all the models.

Synthesis, biological evaluation and in silico metabolic and toxicity prediction of some flavanone derivatives

Flavones chemically are anthoxanthins, occur either in the free state or as glycosides associated with tannins (flavanoids). Flavanoids (derivatives of flavone) possess various pharmacological activities and due to its xanthine-oxidase enzyme inhibitory effect it also has superoxide-scavenging activities. A series of 2-phenyl-2,3-dihydrochromon-4-one derivatives (flavanone derivatives) were synthesized from chalcones by cyclization method and their activities were evaluated against some gram positive and gram-negative bacteria. IR, NMR and CHN analysis confirmed the structure of the synthesized compounds. The results of the antibacterial studies shows that compounds 2b, 2e, 2f and 2h possess activity against many bacterial strains. Among that the compound (2h) has remarkable activity against all strains viz. 25 μg/ml inhibitory concentration against S. aureus, S. sonnei, E. coli, S. typhimurium and V. cholerae. Compound 2f possess minimum inhibitory concentration of 200 μg/ml against E. coli and S. typhimurium and 25 μg/ml against S. sonnei, S. dysenteriae and V. cholerae. In silico metabolic and toxicity study of the synthesized compounds were performed and the predicted result showed that the compound having hydroxyl functional group undergo sulfate and O-glucuronide conjugation reaction and methoxy derivatives undergo demethylation reaction. The biologically active compounds are free of toxicity in oncogene, teratogen, sensitivity and immunotoxicity.

Synthesis and PPAR-γ ligand-binding activity of the new series of 2′-hydroxychalcone and thiazolidinedione derivatives

Fifteen chalcones and three thiazolidinedione (TZD) chalcones were prepared to evaluate their peroxisome proliferator-activated receptor-γ (PPAR-γ) ligand-binding activities. Among the three TZDs, one compound possessed PPAR-γ transactivation potential, while the others showed antagonistic activity against PPAR-γ transactivation. Among the chalcones, compound 5 was the most potent, and structure-activity relationship studies indicated that a methoxyl group in position C-4 and hydroxyl group in position C-4′ or 5′ in chalcone plays a key role in determining the potency of PPAR-γ activation.

Cytotoxic 2',5'-dihydroxychalcones with unexpected antiangiogenic activity.

A series of 2',5'-dihydroxychalcones were synthesized and evaluated for cytotoxicity against tumor cell lines and human umbilical venous endothelial cells (HUVEC). It was found that chalcones with electron-withdrawing substituents on the B ring exhibited potent cytotoxicity against a variety of tumor cell lines while compounds with electron-releasing groups were less potent in general. Those compounds with B ring replaced by extended or heteroaromatic rings exhibited significant bioactivity. Several compounds were shown to have marked cytotoxic selectivity towards HUVECs. Especially, among the synthesized compounds, 2-chloro-2',5'-dihydroxychalcone (2-3) showed the highest selectivity index up to 66 in comparison to HCT116 cells. This compound also exhibited strong inhibitory effects on the HUVEC tube formation in an in vitro model. When administered into BDF1 mice bearing Lewis lung carcinoma cells at 50 mg kg(-1) day(-1), 2-3 was found to inhibit the growth of tumor mass by 60.5%.