56074-71-6

Upstream product

• 870-63-3 prenyl bromide 
• 99-93-4 4-Hydroxyacetophenone 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 99-93-4 4-Hydroxyacetophenone 
• 1313892-35-1 (E)-3-(5-bromo-2,4-dihydroxyphenyl)-1-(4-methoxy-3-(3-methylbut-3-en-2-yl)phenyl)prop-2-en-1-one 
• 1313892-41-9 C₂₆H₂₉BrO₅ 
• 1313891-14-3 1-(4-hydroxy-3-(3-methylbut-3-en-2-yl)phenyl)ethanone 
• 1313891-24-5 1-(4-methoxy-3-(3-methylbut-3-en-2-yl)phenyl)ethanone 
• 2079-53-0 1-(4-(allyloxy)phenyl)ethanone 
• 1528739-00-5 (E)-3-(3,4-diethoxymethoxy-2-methoxyphenyl)-1-[4-(3-methylbut-2-enyloxy)phenyl]prop-2-en-1-one 
• 1528739-01-6 (E)-3-(3,4-dihydroxy-2-methoxyphenyl)-1-[4-hydroxy-3-(1,1-dimethylprop-2-enyl)phenyl]prop-2-en-1-one 
• 1615245-48-1 (E)-3-(4-(dimethylamino)phenyl)-1-(4-((3-methylbut-2-en-1-yl)oxy)phenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Functionalization of the chalcone scaffold for the discovery of novel lead compounds targeting fungal infections

The occurrence of invasive fungal infections represents a substantial threat to human health that is particularly serious in immunocompromised patients. The limited number of antifungal agents, devoid of unwanted toxic effects, has resulted in an increased demand for new drugs. Herein, the chalcone framework was functionalized to develop new antifungal agents able to interfere with cell growth and with the infection process. Thus, a small library of chalcone-based analogues was evaluated in vitro against C. albicans ATCC 10231 and a number of compounds strongly inhibited yeast growth at non-cytotoxic concentrations. Among these, 5 and 7 interfered with the expression of two key virulence factors in C. albicans pathogenesis, namely, hyphae and biofilm formation, while 28 emerged as a potent and broad spectrum antifungal agent, enabling the inhibition of the tested Candida spp. and non-Candida species. Indeed, these compounds combine two modes of action by selectively interfering with growth and, as an added value, weakening microbial virulence. Overall, these compounds could be regarded as promising antifungal candidates worthy of deeper investigation. They also provide a chemical platform through which to perform an optimization process, addressed at improving potency and correcting liabilities.

Design, synthesis, docking studies and monoamine oxidase inhibition of a small library of 1-acetyl- and 1-thiocarbamoyl-3,5-diphenyl-4,5-dihydro-(1h)-pyrazoles

New N-acetyl/N-thiocarbamoylpyrazoline derivatives were designed and synthesized in high yields to assess their inhibitory activity and selectivity against human monoamine oxidase A and B. The most important chiral compounds were separated into their single enantiomers and tested. The impact of the substituents at N1, C3 and C5 positions as well the influence of the configuration of the C5 on the biological activity were analyzed. Bulky aromatic groups at C5 were not tolerated. p-Prenyloxyaryl moiety at C3 oriented the selectivity toward the B isoform. The results were also corroborated by molecular modelling studies providing new suggestions for the synthesis of privileged structures to serve as lead compounds for the treatment of mood disorders and neurodegenerative diseases.

Regioselective Copper-Catalyzed Oxidative Coupling of α-Alkylated Styrenes with Tertiary Alkyl Radicals

A radical-mediated oxidative cross-coupling of readily accessible α-alkylated styrenes with 1,3-dicarbonyl compounds utilizing a combination of Cu(OAc)2 and air as a catalytic system is described. Rather than requiring α-halocarbonyl compounds, this efficient approach enables direct installation of tertiary functionalized alkyl motifs to olefins with simple carbonyl derivatives. The novel protocol is characterized with high allylic selectivities via a competing β-H elimination. Both radical-clock and -trapping experiments provided clear-cut evidence for the intermediacy of an α-keto carbon-centered radical.

Novel licochalcone analogue compounds having anti-inflammatory activity

A licochalcone is known to have various biological activities. However, most licochalcones exhibit cytotoxicity. Licochalcones B and D having a common substituent in an aromatic ring B have been a target for denaturing the structure of an aromatic ring A

Synthesis of licochalcone analogues with increased anti-inflammatory activity

Licohalcones have been reported to have various biological activities. However, most of licochalcones also showed cytotoxicity even though their versitile utilities. Licochalcones B and D, which have common substituents at aromatic ring B, are targeted to

Highly efficient and selective deprotection method for prenyl, geranyl, and phytyl ethers and esters using borontrifluoride-etherate

An efficient, simple, and practical method has been developed for the deprotection of prenyl, geranyl, and phytyl ethers and esters of aromatic and aliphatic compounds using borontrifluoride-etherate (BF3· OEt2) at room temperature in good to excellent yields for the first time. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Copyright Taylor & Francis Group, LLC.

Natural Products as Sources of New Fungicides (I): Synthesis and Antifungal Activity of Acetophenone Derivatives Against Phytopathogenic Fungi

Several series of 45 acetophenone derivatives bearing various alkyl or benzyl substituents were conveniently synthesized and their structures characterized by 1H and 13C NMR spectroscopy, HRMS and single-crystal X-ray analysis. Their in vitro antifungal activities against a panel of phytopathogenic fungi were evaluated by mycelial growth rate assay. Of them, 12 derivatives (e.g., 3a-c, 4c and 4e) exhibited more potent antifungal effects on some phytopathogens than a commercial fungicide hymexazol as positive control. In particular, compound 3b with IC50 values of 10-19μg/mL was found to be the most active in this series and might be a potential lead structure for further optimization. The preliminary structure-activity relationship (SAR) studies of a series of acetophenones are also discussed. A series of acetophenone derivatives have been synthesized and tested for their antifungal activities. Of them 12 derivatives exhibited more potent antifungal effects on some phytopathogens than a positive control hymexazol. Especially, compound 3b (IC50=10-19μg/mL) was found to be the most active and might be a potential lead structure. The SAR of these acetophenones is also discussed.

Regioselectivity in the ene reaction of singlet oxygen with ortho-prenylphenol derivatives

The ene reaction of singlet oxygen with prenylated dihydroxyacetophenones led to the 2-hydroperoxy-3-methylbut-3-enyl derivatives as the major product. This original regioselectivity outlined a new effect, in competition with the previously established la

Synthesis and evaluation of 4-(3-methyl-2-butenoxy) isonitrosoacetophenone, a radiation-induced stress metabolite in Citrus

The time- and dose-dependent occurrence of 4-(3-methyl-2- butenoxy)isonitrosoacetophenone, a γ-irradiation-induced stress metabolite was investigated. The chemical synthesis of the compound is reported. The compound exhibits antifungal activity, as well as antioxidant activity, as indicated by its ability to scavenge reactive oxygen radicals in a chemiluminescence assay.