119271-85-1

Upstream product

• 98-03-3 thiophene-2-carbaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 65009-00-9 O-phenyl N,N-diethylcarbamate 
• 19311-91-2 N,N-diethylsalicylamide 
• 32865-61-5 2-iodophenyl acetate 
• 19212-35-2 1-(thiophen-2-yl)prop-2-yn-1-ol 
• 204703-70-8 1-(2-(tetrahydro-2H-pyran-2-yloxy)phenyl)ethanone 
• 261785-35-7 3-(o-acetoxyphenyl)-1-(2'-thienyl)prop-2-yn-ol 
• 28424-61-5 3-thiophen-2-yl-acryloyl chloride 
• 108-95-2 phenol 

Downstream Products

• 55557-62-5 5-(2-thienyl)-4,5-dihydro-3-(2-hydroxyphenyl)pyrazole 
• 1330048-57-1 3-(2-hydroxyphenyl)-1-(thiophen-2-yl)propan-1-one 
• 1373122-04-3 1-(2-hydroxyphenyl)-3-(phenylthio)-3-(thiophen-2-yl)propan-1-one 
• 1058163-31-7 C₁₉H₁₅NOS₂ 
• 6297-63-8 2-(2-thienyl)-4H-1-benzopyran-4-one 
• 98696-87-8 3-(2”-thienyl)-1-(2’-hydroxyphenyl)-propan-1-one 
• 91805-20-8 3-hydroxy-2-(thiophene-2-yl)-4H-chromen-4-one 

Relevant academic research and scientific papers

Identification of chalcones as in vivo liver monofunctional phase II enzymes inducers

Cancer preventive agents (CPA) are drugs able to suppress the carcinogen metabolic activation or block the formation of ultimate carcinogens. CPA could act through various molecular mechanisms, for example by interfering with the action of procarcinogen. This could be attained by increasing the phase II enzymes levels of quinone reductase (QR) and glutathione S-transferase (GST). New flavonoids, especially chalcones, have been identified as in vivo monofunctional phase II enzymes inducers. Oral administration of chalcone, 4, and both p-methoxy-substituted chalcones, 6 and 14, increased hepatic QR activity with concomitant decrease in CYP1A1 activity, a member of the most important group of phase I enzymes cytochrome P450. Among them, 4 also increased GST activity. While p-bromo-substituted chalcone 8 was the best inducer of QR it decreased hepatic GST expression and cytochrome P450, being the most effective decreasing cytochrome P450-expression. Thienyl-chalcone 20 being the bioisostere of chalcone 4 did not display the same in vivo profile in the phase I level modification. As chalcone 4 its bioisostere, chalcone 20, displayed low DNA strand breakage and absence of mutagenicity. Also, in our preliminary in vivo tumourigenesis/chemopreventive and acute-toxicity studies, chalcones 4, 6 and 8 showed the best behaviours as CPA justifying additional studies that are ongoing.

Design, synthesis, and biological evaluation of Helicobacter pylori inosine 5′-monophosphate dehydrogenase (HpIMPDH) inhibitors

Inosine 5′-monophosphate dehydrogenase (IMPDH) catalyzes a crucial step in the biosynthesis of guanine nucleotides. Being a validated target for immunosuppressive, antiviral, and anticancer drug development, lately it has been exploited as a promising target for antimicrobial therapy. Extending our previous work on Mycobacterium tuberculosis IMPDH, GuaB2, inhibitor development, we screened a set of 23 new chemical entities (NCEs) with substituted flavone (Series 1) and 1,2,3-triazole (Series 2) core structures for their in vitro Helicobacter pylori IMPDH (HpIMPDH) and human IMPDH2 (hIMPDH2) inhibitory activities. All the NCEs possessed acceptable molecular, physicochemical, and toxicity property profiles. The ranges for HpIMPDH and hIMPDH2 inhibition were 9–99.9% and 16–57%, respectively, at 10 μM concentration. The most potent HpIMPDH inhibitor, 25c, exhibited IC50 value of 1.27 μM with no hIMPDH2 inhibitory activity. The moderately potent, structurally novel hit molecule, 25c, may serve as a lead for further design and development of highly potent HpIMPDH inhibitors.

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.

Photoreactions of 2-(furan-2-yl)-3-hydroxy-4H-chromen-4-one and 3-hydroxy-2-(thiophene-2-yl)-4 H -chromen-4-one using cyclohexane and acetonitrile as solvents

Photolysis of the titled chromenones was carried out at their longest absorption band (～360 nm) using cyclohexane (CH) and acetonitrile (ACN) as solvents, in both aerated and de-aerated solutions. Different dimeric photoproducts were formed with both chromenones in aerated solutions. On photolysing 2-(furan-2-yl)-3-hydroxy-4H-chromen-4-one (FHC) in aerated cyclohexane, 2-(furan-2-yl)-2-{[2-(furan-2yl)-4-oxo-4H-chromen-3-yl]oxy}-2H-chromene-3,4-dione (a dehydrodimer) was formed, and on photolysing 3-hydroxy-2-(thiophene-2-yl)-4H-chromen-4-one (THC) in aerated ACN, a different dimeric product was isolated and identified. The corresponding 3-aryl-3-hydroxy-1,2-indandiones were also detected with FHC in ACN and with THC in CH, in addition to the dimeric products in both cases. On the other hand, in the de-aerated solutions, only the corresponding 1,2-indandiones were detected. 3-(Furan-2-yl)isobenzofuran-1(3H)-one as a secondary product was also detected with FHC in both solvents. An attempt was made to isolate the spectra of the photoproducts in situ. Excited State Intramolecular Proton Transfer (ESIPT) and Excited State Intramolecular Charge Transfer (ESICT) processes complicate the photodynamics of the reaction, making it difficult to predict the mechanisms of the photoreactions. However, tentative mechanisms have been proposed for the formation of the photoproducts.

Design, synthesis and MAO inhibitory activity of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives

A series of 2-(arylmethylidene)-2,3-dihydro-1-benzofuran-3-one derivatives (aurones, 1–20) were synthesized and screened for their inhibitory activity against hMAO. Seventeen compounds (1–5, 7–17, 19) were found to be selective towards hMAO-B, while two w

Synthesis and characterization of Ru(II)-DMSO-Cl-chalcone complexes: DNA binding, nuclease, and topoisomerase II inhibitory activity

The complexes of type cis-[Ru(S-DMSO)3(R-CO-CH-CH-R′)Cl] (R = 2-hydroxyphenyl for all, R′ = phenyl 1, naphthyl 2, anthracenyl 3, thiophene 4, 3-methyl thiophene 5) are synthesized and characterized using spectroscopic (IR, 1H and su

Thallium(III) p-tosylate-mediated oxidative [1,2] rearrangement of 2-naphthyl and 2-heteroarylchromanones

A practical and effective approach towards the synthesis of 3-heteroaryl-4H-chromen-4-ones by the oxidative [1,2] rearrangement of the respective 2-heteroaryl chroman-4-ones using thallium(III) p-tosylate is presented. The oxidative rearrangement of α- an

Exploring 3-hydroxyflavone scaffolds as mushroom tyrosinase inhibitors: synthesis, X-ray crystallography, antimicrobial, fluorescence behaviour, structure-activity relationship and molecular modelling studies

To explore new scaffolds as tyrosinase enzyme inhibitors remain an interesting goal in the drug discovery and development. In due course and our approach to synthesize bioactive compounds, a series of varyingly substituted 3-hydroxyflavone derivatives (1-23) were synthesized in one-pot reaction and screened for in?vitro against mushroom tyrosinase enzyme. The structures of newly synthesized compounds were unambiguously corroborated by usual spectroscopic techniques (FTIR, UV-Vis, 1H-, 13C-NMR) and mass spectrometry (EI-MS). The structure of compound 15 was also characterized by X-ray diffraction analysis. Furthermore, the synthesized compounds (1-23) were evaluated for their antimicrobial potential. Biological studies exhibit pretty good activity against most of the bacterial-fungal strains and their activity is comparable to those of commercially available antibiotics i.e. Cefixime and Clotrimazole. Amongst the series, the compounds 2, 4, 5, 6, 7, 10, 11, 14 and 22 exhibited excellent inhibitory activity against tyrosinase, even better than standard compound. Remarkably, the compound 2 (IC50 = 0.280 ± 0.010 μg/ml) was found almost sixfold and derivative 5 (IC50 = 0.230 ± 0.020 μg/ml) about sevenfold more active as compared to standard Kojic acid (IC50 =1.79 ± 0.6 μg/ml). Moreover, these synthetic compounds (1-23) displayed good to moderate activities against tested bacterial and fungal strains. Their emission behavior was also investigated in order to know their potential as fluorescent probes. The molecular modelling simulations were also performed to explore their binding interactions with active sites of the tyrosinase enzyme. Limited structure-activity relationship was established to design and develop new tyrosinase inhibitors by employing 2-arylchromone as a structural core in the future. Communicated by Ramaswamy H. Sarma.

Substituent-Controlled Divergent Cascade Cycloaddition Reactions of Chalcones and Arylalkynols: Access to Spiroketals and Oxa-Bridged Fused Heterocycles

Herein, we report substituent-controlled divergent cascade cycloaddition reactions of chalcones and arylalkynols in the presence of PtI2. Depending on the substituent on the chalcone, either spiroketals or oxa-bridged fused heterocycles could be obtained in the ranges of 86–97% and 87–95% yields under identical reaction conditions. Control experiments were carried out to elucidate the origin of the high chemoselectivity. These provide a method for the synthesis of a diverse array of structurally complex oxygen-containing heterocycles. (Figure presented.).

Glycolytic inhibition and antidiabetic activity on synthesized flavanone scaffolds with computer aided drug designing tools

Background: Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs avail-able in the market in long-term use may lead to serious adverse effects. He