24672-82-0

Usage

Preparation

Obtained (poor yield) by reaction of 2-methyl-but-3-en-2-ol on resacetophenone with boron trifluoride etherate in dioxane at r.t. (6%).

Upstream product

• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 870-63-3 prenyl bromide 
• 115-18-4 2-methyl-3-buten-2-ol 

Downstream Products

• 63529-05-5 (E)-1-(2,4-dihydroxy-3,5-bis(3-methylbut-2-en-1-yl)phenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one 
• 141803-60-3 2',4'-dihydroxy-3,4-dimethoxy-3',5'-bis(3-methylbut-2-enyl)chalcone 
• 141803-59-0 2',4'-dihydroxy-2,4-dimethoxy-3',5'-bis(3-methylbut-2-enyl)chalcone 
• 1001906-02-0 1-[2,4-dihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]-3-pyridin-3-ylpropenone 
• 1001906-03-1 3-(2,4-dichlorophenyl)-1-[2,4-dihydroxy-3,5-bis(3-methylbut-2-enyl)phenyl]propenone 
• 71978-75-1 1-[2,4-dihydroxy-3,5-bis-(3-methyl-but-2-enyl)-phenyl]-3-(4-hydroxy-phenyl)-propenone 
• 217442-57-4 (E)-3-(2,2-dimethyl-2H-chromen-6-yl)-1-[2-hydroxy-3,5-bis(3,3-dimethylallyl)-4-methoxymethyloxyphenyl]-2-propen-1-one 
• 217442-59-6 2-hydroxy-3,5-bis(3,3-dimethylallyl)-4-methoxymethyloxyacetophenone 

Relevant academic research and scientific papers

A PRENYLATED CHALCONE FROM CROTALARIA MEDICAGINEA

Key Word Index-Crotalaria medicaginea; Leguminosae; roots; 3',5'-di-isopentenyl; 2',4',4-trihydroxy chalcone. A new prenylated chalcone has been characterized from the root of Crotalaria madicaginea.

Synthetic methods for prenylated chalcones and pyranochalcones

The inventors of the present invention invented a simple and effective way to synthesize compounds 1-9 of natural prenylated chalcones and pyrano chalcones by using Claisen-Schmidt condensation as a main step. In addition, an anti-inflammatory effect of synthetic compounds was evaluated in RAW 264.7 macrophages which were stimulated with a lipopolysaccharide. As a result, chalcone compounds having prenyl groups in a ring A (an acetophenone part) show weak inhibition or no inhibition on the generation of nitrogen oxide while chalcones (5, 6, 8, and 9) having no prenyl groups in the ring A show normal or good activity, and have no cytotoxicity.COPYRIGHT KIPO 2017

Synthesis and pharmacological properties of naturally occurring prenylated and pyranochalcones as potent anti-inflammatory agents

An efficient approach has been developed for the synthesis of naturally occurring prenylated chalcones viz. kanzonol C (1), stipulin (2), crotaorixin (3), medicagenin (4), licoagrochalcone A (5) and abyssinone D (6) along with the pyranochalcones paratocarpin C (7), anthyllisone (8) and 3-O-methylabyssinone A (9). The key step of the synthesis is a Claisen-Schmidt condensation. Subsequently, their anti-inflammatory effects were investigated in lipopolysaccharides (LPSs)-induced RAW-264.7 macrophages. Of the synthesized chalcones, compounds 5 (IC50 = 10.41 μmol/L), 6 (IC50 = 9.65 μmol/L) and 8 (IC50 = 15.34 μmol/L) show remarkable activity with no cytotoxicity. Compound 9 (IC50 = 4.5 μmol/L) exhibits maximum (83.6%) nitric oxide (NO) inhibition, but shows slight cytotoxicity. The results reveal that the chalcones bearing the prenyl group at 3- and/or 5-position on ring A (acetophenone moiety), i.e., 1-4 and 7 show weak, or no inhibition activity, whereas chalcones having the prenyl group only on ring B (aldehyde part), i.e., 5, 6 and 8 show significant activity on the production of inflammatory mediated NO with no cytotoxicity.

Synthesis and insight into the structure-activity relationships of chalcones as antimalarial agents

Licochalcone A (I), isolated from the roots of Chinese licorice, is the most promising antimalarial compound reported so far. In continuation of our drug discovery program, we isolated two similar chalcones, medicagenin (II) and munchiwarin (III), from Crotalaria medicagenia, which exhibited antimalarial activity against Plasmodium falciparum. A library of 88 chalcones were synthesized and evaluated for their in vitro antimalarial activity. Among these, 67, 68, 74, 77, and 78 exhibited good in vitro antimalarial activity against P. falciparum strains 3D7 and K1 with low cytotoxicity. These chalcones also showed reduction in parasitemia and increased survival time of Swiss mice infected with Plasmodium yoelii (strain N-67). Pharmacokinetic studies indicated that low oral bioavailability due to poor ADME properties. Molecular docking studies revealed the binding orientation of these inhibitors in active sites of falcipain-2 (FP-2) enzyme. Compounds 67, 68, and 78 showed modest inhibitory activity against the major hemoglobin degrading cysteine protease FP-2.

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.

Total synthesis of munchiwarin, a triprenylated chalcone from Crotalaria medicagenia

An efficient method is developed for the synthesis of the modified triprenylated chalcone, munchiwarin (1), isolated from the roots of Crotalaria medicagenia. The synthesis of 1 utilizes a Claisen-Schmidt condensation between 2,4-dihydroxy-3,5-C-diprenyl

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

Syntheses of (+/-)-shinflavanone and its structural analogues as potent inhibitors of bone resorption pits formation.

The first total syntheses of (+/-)-shinflavanone and its structural analogues were achieved. (+/-)-Shinflavanone, appears to be a strong inhibitor of bone resorption pits formation by osteoclast-like cell induced by 1alpha, 25-dihydroxy vitamine D3 (IC50 = 0.70 microg/mL).