60965-24-4

Upstream product

• 598-21-0 2-Bromoacetyl bromide 
• 151-10-0 1,3-Dimethoxybenzene 
• 150-19-6 O-methylresorcine 
• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 

Downstream Products

• 113860-60-9 1-(2-hydroxy-4-methoxy-phenyl)-2-thiocyanato-ethanone 
• 55960-07-1 2,2'-dihydroxy-4'-methoxyacetophenone 
• 1381777-49-6 2-(imidazo[1,2-a]pyridin-2-yl)-5-methoxyphenol 
• 1403876-02-7 1-(2-hydroxy-4-methoxyphenyl)-2-[4-(4-methylphenyl)-1H-1,2,3-triazol-1-yl]ethan-1-one 
• 1403876-00-5 2-[4-(4-ethylphenyl)-1H-1,2,3-triazol-1-yl]-1-(2-hydroxy-4-methoxyphenyl)ethan-1-one 
• 1403875-99-9 1-(2-hydroxy-4-methoxyphenyl)-2-[4-(4-propylphenyl)-1H-1,2,3-triazol-1-yl]ethan-1-one 
• 1403875-98-8 2-(4-cyclopropyl-1H-1,2,3-triazol-1-yl)-1-(2-hydroxy-4-methoxyphenyl)-ethan-1-one 
• 1403875-97-7 1-(2-hydroxy-4-methoxyphenyl)-2-{4-[(3-metylphenoxy)methyl]-1H-1,2,3-triazol-1-yl}ethan-1-one 
• 1403875-96-6 1-(2-hydroxy-4-methoxyphenyl)-2-{4-[(4-chlorophenoxy)methyl]-1H-1,2,3-triazol-1-yl}ethan-1-one 
• 1315362-38-9 2-azido-1-(2-hydroxy-4-methoxyphenyl)ethanone 

Relevant academic research and scientific papers

A Palladium-Catalyzed Oxa-(4+4)-Cycloaddition Strategy towards Oxazocine Scaffolds

A Pd-catalyzed oxa-(4+4)-cycloaddition between 1-azadienes and (2-hydroxymethyl)allyl carbonates is described. Aurone-derived azadienes furnished polycyclic 1,5-oxazocines in good yields. Interestingly, linear azadienes have also been involved and yielded monocyclic heterocycles with complete regioselectivity. DFT calculations were carried out to gain insight on this observation.

MeONH 2·hCl-Mediated α-Methylenation/Conjugate Addition of α-Sulfonylo-Hydroxyacetophenones with Methyl Sulfoxides: Route to 3-Sulfonylchroman-4-ones

A novel and efficient route for the synthesis of 3-sulfonylchroman-4-ones from α-sulfonyl o -hydroxyacetophenones with methyl sulfoxides via a MeONH 2·HCl-mediated sequential methylenation/ conjugate addition is described. Plausible reaction mechanisms are proposed and discussed. Various reaction conditions for this novel, one-pot, environmentally friendly conversion were investigated.

Nucleus-independent chemical shift (NICS) as a criterion for the design of new antifungal benzofuranones

The assertion made by Wu et al. that aromaticity may have considerable implications for molecular design motivated us to use nucleus-independent chemical shifts (NICS) as an aromaticity criterion to evaluate the antifungal activity of two series of indol-4-ones. A linear regression analysis of NICS and antifungal activity showed that both tested variables were significantly related (p –1 for Candida glabrata, Candida krusei and Candida guilliermondii with compounds 15-32, 15-15 and 15-1. The MIC for filamentous fungi was 1.95 μg·mL–1 for Aspergillus niger for compounds 15-1, 15-33 and 15-34. The results obtained support the use of NICS in the molecular design of compounds with antifungal activity.

Benzo[d]imidazo[2,1-b]thiazole-based fluorescent sensor for Zn2+ ion detection

In this study, we have synthesized and evaluated three benzo[d]imidazo[2,1-b]thiazole-based sensors (BIT-1, BIT-2 and BIT-3). Among them, BIT-3 namely 2-(benzo[d]imidazo[2,1-b]thiazol-2-yl)-5-methoxyphenol was introduced as a selective fluorescence chemosensor for Zn2+ ion detection. The presence of zinc ions enhanced fluorescence property of BIT-3 at 404 nm due to formation of a 1:1 complex between the chemosensor and the Zn2+ ion. Control experiments showed that the analogous ions do not have fluorescence enhancement effect and some of them even quench the fluorescence dramatically. The data obtained from UV–vis absorption analysis, fluorescence measurements and 1H NMR spectroscopy approved the interaction between BIT-3 and Zn2+ ion. The sensor probe BIT-3 exhibits a selective fluorescence enhancing property via a chelation-enhanced fluorescence (CHEF) upon addition of Zn2+. Thus, a selective fluorescent chemosensor BIT-3 establishes an important sensing platform for real-time monitoring of Zn2+ ion in aqueous environment.

PdCl2/CuCl2/Bi(OTf)3-promoted Construction of Sulfonyl Dibenzooxabicyclo[3.3.1]nonanes and Arylnaphthalenes via Intramolecular Annulation of Sulfonyl o-Allylarylchromanones

PdCl2/CuCl2/Bi(OTf)3-promoted intramolecular domino annulation of sulfonyl o-allylarylchromanones provides tetracyclic sulfonyl dibenzooxabicyclo[3.3.1]nonanes and bicyclic arylnaphthalenes with good to excellent yields in MeOH at room (25 °C) and refluxing (65 °C) temperature, respectively. The starting sulfonyl o-allylarylchromanones can be easily obtained from the intermolecular cyclocondensation of α-sulfonyl o-hydroxyacetophenones and o-allylbenzaldehydes. The uses of various catalysts and solvent systems are investigated herein for convenient transformation. A plausible mechanism is proposed and discussed. This protocol provides one-pot ring closure via carbon-carbon (C?C) bond formation. (Figure presented.).

Temperature-Controlled Desulfonylative Condensation of α-Sulfonyl o-Hydroxyacetophenones and 2-Formyl Azaarenes: Synthesis of Azaaryl Aurones and Flavones

Temperature-controlled intermolecular desulfonylative condensation of α-sulfonyl o-hydroxyacetophenones with 2-formyl azaarenes (pyridines and quinolones) provides azaaryl (pyridyl and quinolyl) aurones and flavones under warming and refluxing toluene reaction conditions via the formation of the intermediate of sulfonyl chroman-4-one. The uses of various solvents are investigated for facile and efficient transformation. A plausible mechanism is proposed.

New dioxido-vanadium(V) complexes containing hydrazone ligands: Syntheses, crystal structure and their catalytic application toward C–H bond functionalization

New dioxido-vanadium(V) complexes derived from hydrazone ligands have been synthesized in good yield. The complexes were characterized by elemental analysis, IR, UV–Visible and 1H NMR spectroscopies. The structure of both the complexes was established by Single Crystal X-ray crystallography. Complex 1 crystallized in monoclinic P21/n space group, with cell parameters a = 8.3725(5) ? b = 15.0475(17) ? c = 32.227(3) ? α = 90° β = 91.846(5)o, γ = 90°. Complex 2 crystallized in triclinic P-1 space group, a = 8.1871(7) ? b = 11.2605(17) ? c = 11.4031(18) ? α = 105.961(14)° β = 110.528(12)o and γ = 96.387(10)o. Both the complexes act as efficient catalyst which can catalyse the C–H bond functionalization reaction.

Natural products as sources of new fungicides (V): Design and synthesis of acetophenone derivatives against phytopathogenic fungi in vitro and in vivo

A series of acetophenone derivatives (10a–10i, 11, 12a–12g, 13a–13g, 14a–14d and 15a–15l) were designed, synthesized and evaluated for antifungal activities in vitro and in vivo. The antifungal activities of 53 compounds were tested against several plant pathogens, and their structure–activity relationship was summarized. Compounds 10a–10f displayed better antifungal effects than two reference fungicides. Interestingly, the most potent compound 10d exhibited antifungal properties against Cytospora sp., Botrytis cinerea, Magnaporthe grisea, with IC50 values of 6.0–22.6 μg/mL, especially Cytospora sp. (IC50 = 6.0 μg/mL). In the in vivo antifungal assays, 10d displayed the significant protective efficacy of 55.3% to Botrytis cinerea and 73.1% to Cytospora sp. The findings indicated that 10d may act as a potential pesticide lead compound that merits further investigation.

Design and synthesis of novel senkyunolide analogues as neuroprotective agents

A class of senkyunolide analogues bearing benzofuranone fragment were designed, synthesized and evaluated for their neuroprotective effect in models of oxygen glucose deprivation (OGD) and oxidative stress. All tested compounds showed neuroprotection profile based on the cell viability assay. In particular, derivatives 1f–1i possessing furoxan-based nitric oxide releasing functionality exhibited significant biological activities in OGD models. More importantly, compound 1g containing short linker with furoxan displayed the most potent neuroprotection at the concentration of 100 μM (cell survival up to 145.2%). Besides, 1g also showed the middle level neuroprotective effect in model of oxidative stress.

Synthesis and evaluation of paeonol derivatives as potential multifunctional agents for the treatment of alzheimer's disease

(A.H.); Alzheimer's disease (AD) is a progressive neurodegenerative brain disorder characterized by memory loss, language impairment, personality changes and intellectual decline. Taking into account the key pathological features of AD, such as low levels of acetylcholine, beta-amyloid (Aβ) aggregation, oxidative stress and dyshomeostasis of biometals, a new series of paeonol derivatives 5a-5d merging three different functions, i.e., antioxidant, anti-acetylcholinesterase (AChE) activity, metal chelating agents for AD treatment have been synthesized and characterized. Biological assays revealed that compared with paeonol (309.7 μM), 5a-5d had a lower DPPH IC50 value (142.8-191.6 μM). 5a-5d could significantly inhibit hydrogen peroxide-induced neuronal PC12 cell death assessed by MTT assay in the concentration range of 5-40 μM. AChE activity was effectively inhibited by 5a-5d, with IC50 values in the range of 0.61-7.04 μM. 5a-5d also exhibited good metal-chelating ability. All the above results suggested that paeonol derivatives may be promising multifunctional agents for AD treatment.