125574-15-4

Upstream product

• 90-15-3 α-naphthol 
• 102-92-1 cinnamoyl chloride 
• 711-79-5 1-hydroxy-2-acetonaphthone 
• 100-52-7 benzaldehyde 
• 140-10-3 (E)-3-phenylacrylic acid 
• 6051-86-1 2-phenyl-2H-benzo[h]chromen-4(3H)-one 
• 67-63-0 isopropyl alcohol 
• 61912-14-9 2-naphthyl diethylcarbamate 
• 129986-83-0 (E)-1-(1-Methoxymethoxy-naphthalen-2-yl)-3-phenyl-prop-2-en-1-ol 
• 7382-37-8 1-(methoxymethyloxy)naphthalene 
• 14371-10-9 (E)-3-phenylpropenal 
• 129986-92-1 (E)-1-(1-Methoxymethoxy-naphthalen-2-yl)-3-phenyl-propenone 

Downstream Products

• 116491-39-5 6-Phenyl-6H-5-oxa-11,12-diaza-benzo[b]chrysene 
• 6051-86-1 2-phenyl-2H-benzo[h]chromen-4(3H)-one 
• 100-52-7 benzaldehyde 
• 129457-25-6 nickel(II){3-(1-hydroxy-2-naphthyl)-5-(phenyl)}2 dihydrate 
• 129457-30-3 copper(II){3-(1-hydroxy-2-naphthyl)-5-(phenyl)pyrazoline}2 
• 129457-24-5 zinc(II){3-(1-hydroxy-2-naphthyl)-5-(phenyl)pyrazoline}2 
• 1413433-54-1 C₁₉H₁₄O₂ 
• 1413433-55-2 C₁₉H₁₄O₂ 
• 80309-00-8 1-(4-bromo-1-hydroxy-[2]naphthyl)-3t-phenyl-propenone 
• 30508-14-6 (2RS,3SR)-2,3-dibromo-1-(4-bromo-1-hydroxy-[2]naphthyl)-3-phenyl-propan-1-one 
• 79387-87-4 1-(1-hydroxynaphthalen-2-yl)-3-phenylpropan-1-one 
• 604-59-1 α-naphtoflavone 
• 1456866-17-3 3-methoxy-2-phenyl-4H-benzo[h]chromen-4-one 
• 22812-50-6 3-hydroxy-2-phenyl-4H-benzo[h]chromen-4-one 

Relevant academic research and scientific papers

Synthesis and in-silico molecular modelling, DFT studies, antiradical and antihyperglycemic activity of novel vanadyl complexes based on chalcone derivatives

Diabetes mellitus (DM) will be one of the ten most deadly diseases in the near future, according to a WHO survey. It is, therefore, of utmost importance to design and synthesize effective inhibitors to be used in the treatment of DM disease. In this respect, a new series of chalcone derivatives and their vanadyl complexes of composition [VO(LI-III)2]SO4 and [VO(LIV)2] (where LI=1-(2-Hydroxy-phenyl)-3-phenyl-propenone, LII=1-(1-Hydroxy-naphthalen-2-yl)-3-phenyl-propenone, LIII = 1-(2-Amino-phenyl)-3-phenyl-propenone, LIV = 4-Hydroxy-6-methyl-3-(3-phenyl-acryloyl)-pyran-2-one) were designed and synthesized in this work. Physioanalytical, FTIR, 1H NMR, 13C NMR, UV-Visible, EPR, SEM, EDX, and mass spectrometry data were used to establish their formation and validate their structures. After that, biological effects such as antiradical, α-glucosidase, and α-amylase inhibitory activities of synthesized vanadyl-chalcone complexes were assessed. Furthermore, the Density Functional Theory (DFT) studies with 6-31G*/B3LYP level were used to achieve optimal molecular geometries and HOMO-LUMO gap to analyze the chemical and kinetic stability of the complexes. Molecular docking studies were performed as well to investigate the interactions between the synthesized complexes and target enzyme viz. α-amylase and α-glucosidase. The in-vitro biological studies showed major and significant improvements upon the complexation of ligands. Complex 3 (for α-glucosidase) and complex 4 (for α-amylase), in particular, were found to have a remarkable ability to lower blood sugar levels. Otherwise, the potent α-glucosidase and α-amylase inhibitory activity was observed in all of the synthesized complexes. The complexes with the best IC50 values were studied further in terms of enzyme kinetics and displayed mixed inhibition with both enzymes. Furthermore, using the DPPH assay, the antiradical activity of chalcones and their vanadyl complexes was evaluated for their efficacy in releasing oxidative stress. From the obtained results, complex 3 and 4 exhibited remarkable antiradical activity.

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Development of benzochalcone derivatives as selective CYP1B1 inhibitors and anticancer agents

A series of benzochalcone derivatives have been synthesized and evaluated for CYP1 inhibitory activity and cytotoxic properties against wild type cell lines (MCF-7 and MDA-MB-231) and drug resistant cell lines (LCC6/P-gp and MCF-7/1B1). All of these compounds were found to have selective inhibition towards CYP1B1 and the most potent two possessed single-digit nanomolar CYP1B1 potency. In addition, some of them showed promising cytotoxic activities not only against wild type cells, but also against drug resistant cells at low micromolar concentrations. More importantly, these multi-functional compounds may surmount drug-drug interactions that frequently occur during the combination of CYP1B1/P-gp inhibitors and anticancer drugs to overcome drug resistance. This study may provide a good starting point for the further development of more potent multi-functional agents with CYP1B1 inhibitory activity and cytotoxic potency in cancer prevention and treatment.

From Carbamate to Chalcone: Consecutive Anionic Fries Rearrangement, Anionic Si → C Alkyl Rearrangement, and Claisen-Schmidt Condensation

A highly efficient one-pot procedure was developed for the synthesis of various 2′-hydroxychalcones from phenyl diethylcarbamate, featuring consecutive Snieckus-Fries rearrangement, anionic Si a?' C alkyl rearrangement, and Claisen-Schmidt condensation in a single operation. The applicability of this protocol was demonstrated by the highly efficient synthesis of the anti-inflammatory natural product lonchocarpin. The mechanism insight is also provided.

Extended Aromatic and Heteroaromatic Ring Systems in the Chalcone-Flavanone Molecular Switch Scaffold

Previous work on the o-hydroxychalcone/flavanone molecular switching scaffold showed that simple substitutions alter the pH range in which rapid interconversion occurs. Herein, more impactful structural modifications were performed via alteration of the characteristic phenyl rings to alternative aromatic systems. It was determined that the scaffold was still viable after these changes and that the range of accessible midpoint pH values was markedly increased. To further explore the switch's scope, scaffolds able to have multiple switching events were also investigated.

New hybrid bromopyridine-chalcones as in vivo phase II enzyme inducers: potential chemopreventive agents

Cancer prevention can be achieved by the administration of cancer chemopreventive agents (CCAs) that prevent, delay or reverse the carcinogenic process. CCAs that are able to induce detoxification enzymes, especially monofunctional phase II enzymes, have become an excellent therapeutic strategy. Herein, we report the synthesis of eighteen new potential CCAs, structurally designed to combine (naphtho)chalcone and (bromo)pyridine skeletons. After a selection process involving in vitro phase II induction studies, cytotoxicity against tumoral cells, mutagenicity (the Ames test), and capability for DNA strand breakage (the alkaline comet assay), compound 22, (E)-3-(2-bromopyridin-3-yl)-1-(2-hydroxyphenyl)-2-propen-1-one, was selected for animal studies. The in vivo proof of concept study for derivative 22 demonstrated that it was able to significantly increase the QR and GST activities in the liver, colon and mammary gland without significant induction of the phase I enzyme, CYP. Additionally, we found that for 22 and another in vitro QR activity inducer, (E)-1-(2-hydroxyphenyl)-3-(naphthalen-1-yl)-2-propen-1-one (compound 8), Nrf2 nuclear translocation is operative allowing the exertion of protective effects via the expression of downstream phase II enzymes.

A high sensitive fluorescence turn-on probe for imaging Zn2+ in aqueous solution and living cells

A new pyrazoline-based fluorescent probe was designed and synthesized. The probe can induce a 60-fold fluorescence enhancement after 5 equiv. of Zn 2+ was added, which is superior to a previous report (13-fold), and exhibits high sensitivity and selectivity for response to Zn2+ in aqueous solution. The detection limit and association constant were calculated as 1.23 × 10-7 M and 3.89 × 103 M-1 by a fluorescence titration experiment. The 1:1 binding stoichiometry of L-Zn2+ complex was analysed by Job's plot. The probe showed good reversibility upon addition of EDTA or TPEN. Furthermore, the probe L showed good membrane permeability and can be applied to monitor Zn2+ ions in living HeLa cells.

NHC-catalyzed reaction of enals with hydroxy chalcones: Diastereoselective synthesis of functionalized coumarins

The N-heterocyclic carbene-catalyzed annulation of enals with 2′-hydroxy chalcones afford cyclopentane-fused coumarin derivatives with an excellent level of diastereocontrol. The reaction tolerates a broad range of functional groups; 25 examples are given, and a preliminary mechanistic investigation is provided.

Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2

Multidrug resistance (MDR) often leads to a failure of cancer chemotherapy. Breast Cancer Resistance Protein (BCRP/ABCG2), a member of the superfamily of ATP binding cassette proteins has been found to confer MDR in cancer cells by transporting molecules with amphiphilic character out of the cells using energy from ATP hydrolysis. Inhibiting BCRP can be a solution to overcome MDR.We synthesized a series of flavones, 7,8-benzofl avones and 5,6-benzo flavones with varying substituents at positions 3, 3′ and 4′ of the (benzo)fl avone structure. All synthesized compounds were tested for BCRP inhibition in Hoechst 33342 and pheophorbide A accumulation assays using MDCK cells expressing BCRP. All the compounds were further screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity by calcein AM accumulation assay to check the selectivity towards BCRP. In addition most active compounds were investigated for their cytotoxicity. It was observed that in most cases 7,8-benzoflavones are more potent in comparison to the 5,6-benzoflavones. In general it was found that presence of a 3-OCH3 substituent leads to increase in activity in comparison to presence of OH or no substitution at position 3. Also, it was found that presence of 3′,4′-OCH3 on phenyl ring lead to increase in activity as compared to other substituents. Compound 24, a 7,8-benzoflavone derivative was found to be most potent being 50 times selective for BCRP and showing very low cytotoxicity at higher concentrations.