24672-83-1

Usage

Preparation

Preparation by reaction of prenyl bromide on resacetophenonebr/in the presence of potassium carbonate in refluxing acetone in the presence of potassium hydroxide in methanol, at 0° (14%) or at r.t. (4%) by photochemical method in the presence of benzoyl peroxide in dry benzene for 8 h (10%).

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 870-63-3 prenyl bromide 

Downstream Products

• 93176-13-7 4'-(3,3-dimethylallyloxy)-3-benzyloxy-2'-hydroxy-4-methoxychalcone 
• 886588-96-1 (E)-3-(benzo[d][1,3]dioxol-5-yl)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]prop-2-en-1-one 
• 38965-74-1 Cordoin 
• 1152162-27-0 (E)-1-(2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl)-3-p-tolylprop-2-en-1-one 
• 219119-52-5 1-[2-hydroxy-4-(3-methylbut-2-enyloxy)-phenyl]-3(pyridine-4-yl)-propen-1-one 
• 55524-25-9 4-Hydroxycordoin 
• 1243560-89-5 (E)-3-(3,4-dimethoxyphenyl)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]prop-2-en-1-one 
• 1243560-84-0 (E)-3-(2,3-dimethoxyphenyl)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]prop-2-en-1-one 
• 1243560-87-3 (E)-1-[2-hydroxy-4-(3-methylbut-2-enyloxy)phenyl]-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one 
• 156698-77-0 C₂₇H₂₆O₄ 
• 443684-33-1 C₂₁H₂₂O₃ 
• 1252677-49-8 C₂₀H₁₉ClO₃ 
• 51619-65-9 cordoin 
• 162138-76-3 4-methoxyderricidine 

Relevant academic research and scientific papers

Antibacterial and anti-inflammatory activities of 4-Hydroxycordoin: Potential therapeutic benefits

4-Hydroxycordoin (1), a natural isopentenyloxychalcone, is a plant secondary metabolite that is relatively rare. Since there are very few reports about the biological activities of 1, its potential benefits for periodontal disease were investigated. A mar

Identification of chalcone-based antileishmanial agents targeting trypanothione reductase

All currently used first-line and second-line drugs for the treatment of leishmaniasis exhibit several drawbacks including toxicity, high costs and route of administration. Furthermore, some drugs are associated with the emergence of drug resistance. Thus

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.

Synthesis of isobavachalcone and some organometallic derivatives

Isobavachalcone [2′,4,4′-trihydroxy-3′-(3″-methyl- 2″-butenyl)chalcone, 1] is a prenylated chalcone that has broad biological activity, in particular against neuroblastomas, the most common cancer in infancy. It is currently commercially available at a cost of 190/mg by extraction from Psoralea corylifolia and a number of other African and Asian plants. Several synthetic routes have been explored, and the most efficient procedure involves the palladium-catalysed Stille coupling of 3-iodo-2,4-bis(methoxymethoxy)acetophenone (25) with prenyltributyltin, Claisen-Schmidt condensation with 4-(methoxymethoxy)benzaldehyde to form the triply MOM-protected prenylchalcone 27 and finally deprotection with 2 M HCl in methanol to form isobavachalcone in an overall yield of 15 % over five steps. The X-ray crystal structures of 2,4-dihydroxy-3-iodoacetophenone (21) and of several prenylated chalcones are reported, including the elucidation of their hydrogen-bonding networks in the solid state. The synthetic route has been extended to include organometallic derivatives in which the 4-(methoxymethoxy) benzaldehyde used in the Claisen-Schmidt condensation has been replaced by formylferrocene, formylruthenocene or (η5-formylcyclopentadienyl) (η4-tetraphenylcyclobutadiene)cobalt to form the corresponding analogues of isobavachalcone containing organometallic sandwich moieties.

Structure-activity relationships of chalcone analogs as potential inhibitors of ADP- and collagen-induced platelet aggregation

In an effort to develop potent antiplatelet agents, 12 O-prenylated (2-13) and 10 O-allylated (14-23) chalcones were synthesized and screened for in vitro inhibitory effects on aggregation of washed rabbit platelets induced by ADP (20 μM) and collagen (10

Design, synthesis, and biological evaluation of prenylated chalcones as 5-LOX inhibitors

Ten novel mono- and di-O-prenylated chalcone derivatives were designed on the basis of a homology derived molecular model of 5-lipoxygenase (5-LOX). The compounds were docked into 5-LOX active site and the binding characteristics were quantified using LUD

Synthesis and molecular modelling studies of prenylated pyrazolines as MAO-B inhibitors

A series of N-substituted-3-[(2′-hydroxy-4′-prenyloxy)-phenyl]- 5-phenyl-4,5-dihydro-(1H)-pyrazolines were synthesized and tested on human monoamine oxidase-A and -B isoforms. Structure-activity relationships and molecular modelling showed that some subst

Prenyloxyphenylpropanoids as a novel class of anticonvulsive agents

In this study, we synthesized some natural and semi-synthetic prenyloxyphenylpropanoids (e.g., acetophenones, benzoic and cinnamic acids, chalcones, and coumarins), and we assessed their in vivo neuroprotective activity, using the mouse maximal electrosho

Chalcones: A valid scaffold for monoamine oxidases inhibitors

A large series of substituted chalcones have been synthesized and tested in vitro for their ability to inhibit human monoamine oxidases A and B (hMAO-A and hMAO-B). While all the compounds showed hMAO-B selective activity in the micro- and nanomolar ranges, the best results were obtained in the presence of chlorine and hydroxyl or methoxyl substituents. To better understand the enzyme-inhibitor interaction and to explain the selectivity of the most active compounds toward hMAO-B, molecular modeling studies were carried out on new, high resolution, hMAO-B crystallographic structures. For the only compound that also showed activity against hMAO-A as well as low selectivity, the molecular modeling study was also performed on the hMAO-A crystallographic structure. The docking technique provided new insight on the inhibition mechanism and the rational drug design of more potent/selective hMAO inhibitors based on the chalcone scaffold.