73569-44-5

Upstream product

• 61235-37-8 2-hydroxy-4-(3-methylbut-2-enyloxy)benzaldehyde 
• 95-01-2 2,4-Dihydroxybenzaldehyde 
• 870-63-3 prenyl bromide 
• 18278-34-7 4-hydroxy-2-methoxybenzaldehyde 
• 77-78-1 dimethyl sulfate 

Downstream Products

• 87080-24-8 2-Methoxy-4-(O-prenyl)-4'-methoxymethoxychalcone 
• 1261240-29-2 (E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxy-2-methoxy-5-(2-methylbut-3-en-2-yl)phenyl)prop-2-en-1-one 
• 151410-32-1 (2E)-1-(4-hydroxyphenyl)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}prop-2-en-1-one 
• 18278-34-7 4-hydroxy-2-methoxybenzaldehyde 
• 1292293-96-9 (2E)-3-{2-methoxy-4-[(3-methylbut-2-en-1-yl)oxy]phenyl}-1-[4-(tetrahydro-2H-pyran-2-yloxy)phenyl]prop-2-en-1-one 
• 1189552-11-1 5-(1,2-dimethyl-2-propenyl-1-yl)-4-hydroxy-2-methoxybenzaldehyde 
• 87080-25-9 2-Methoxy-4-acetoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 
• 87080-26-0 4-Hydroxy-2-methoxy-4'-(methoxymethoxy)-5-(α,α-dimethylallyl)chalcone 
• 73569-46-7 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone 
• 87080-27-1 licochalcone A 

Relevant academic research and scientific papers

A short and efficient synthesis of licochalcone E

Licochalcone E was synthesized concisely via an abnormal Claisen rearrangement and Claisen-Schmidt condensation as the key reactions in a three-step sequence. The overall yield is 20% starting from prenyl bromide and 4-hydroxy-2-methoxybenzaldehyde. Georg

Dual-acting diamine antiplasmodial and chloroquine resistance modulating agents

On the basis of structural features known to be critical for the antimalarial activity, accumulation and uptake of chloroquine (CQ), as well as chemosensitization of CQ resistant Plasmodium falciparum, an exploratory novel series of potential dual acting antiplasmodial and chemosensitizing agents was designed and synthesized for biological evaluation. All four compounds contain a common alkyl side chain with two amino groups and differ only in the chemical nature of the hydrophobic aromatic moieties. Among them, N′-[4-(biphenyl-2-ylmethoxy)-benzyl]-N,N-dimethyl-propane-1,3-diamine (P7) displayed the greatest potential as a dual-acting antiplasmodial agent against CQ-resistant strains (I C50K 1 / RSA 11 K1 = 0.67; RMIRSA11 = 0.82) while displaying low in vitro cytotoxicity against a mammalian cell line (CHO). At 1 μM, P7 caused a 8.5 and 4-fold potentiation in CQ accumulation in resistant P. falciparum K1 and RSA11 strains, respectively. In a parallel experiment, 1 μM verapamil showed a 6.5 (K1) and 2 (RSA11)-fold increase in CQ accumulation. The preliminary studies point to structural features that may determine antiplasmodial and/or CQ resistance modulating activity in this new series of compounds. An additive effect was observed against both CQS (D10) and CQR (RSA11) strains when CQ and P7 were used at their corresponding IC50 concentrations in isobologram analysis.

Treatment and prophylaxis of diseases caused by parasites, or bacteria

Aromatic compounds, or prodrugs thereof, which contain an alkylating site and which are capable of alkylating the thiol group in N-acetyl-L-cysteine, in particular bis-aromatic α,β-unsaturated ketones, are used for the preparation of pharmaceutical compositions or medicated feed, food or drinking water for the treatment or prophylaxis of diseases caused by microorganisms or parasites, in particular protozoa such as Leishmannia, Trypanosoma, Toxoplasma, Plasmodium, Pneumocystis, Babesia and Theileria, intestinal protozoa such as Trichormionas and Ciardia; Coccidia such as Eimeria, Isospora, Cryptosporidium; Cappilaria, Microsporidium, Sarcocystis. Trichlodina, Trichoditella, Dacihylogurus, Pseudodacthylogurus, Acantocephalus, Ichthylophtherius, Botrecephalus; and intracellular bacteria, in particular Mycobacterium, Legionella species, Listeria and Salmonella. Preferred compounds have the formula (II): Xm --Ph--C(O)--CH=CH--Ph--Yn, wherein each phenyl group (Ph) may be mono- or polysubstituted; X and Y designate ARH or AZ, wherein A is O, S, NH or N(C1-6 alkyl), RH designates aliphatic hydrocarbyl, and Z is H or a masking group which is decomposed to liberate AH; m is 0, 1 or 2, and n is 0, 1, 2 or 3, whereby, when m is 2, then the two X are the same or different, and when n is 2 or 3, then the two or three Y are the same or different, with the proviso that n and m are not both 0. As examples of such compounds, chalcones, e.g. licochalcone A (obtainable i.a. from batches of Chinese licorice root of Glycyrrhiza species, e.g. G. uralensis or G. inflata) as well as hydroxy, alk(en)yl, and/or alk(en)yloxy analogues thereof are active in vitro and/or in vivo against i.a. L. major and P. falciparum.

Synthesis of licochalkone-A

Claisen rearrangement of 4'-hydroxy-2-methoxy-4-prenyloxychalkone (III) using acetic anhydride in dimethylaniline yields four compounds, viz. 4'-acetoxy-2-methoxy-4'',4'',5''-trimethyldihydrofuranochalkone (IV), 4,4'-diacetoxy-2-methoxy-5-(α,α-dimethylallyl)chalkone (V), 4,4'-diacetoxy-2-methoxy-3-(α,α-dimethylallyl)chalkone (VI) and 4,4'-diacetoxy-2-methoxychalkone (VII).Mild alkaline hydrolysis of V affords 4,4'-dihydroxy-2-methoxy-5-(α,α-dimethylallyl)chalkone (VIII, licochalkone-A).

Synthesis of Licochalcone-A

4,4'-Dihydroxy-2-methoxy-5-(α,α-dimethylallyl)chalcone (VII) (licochalcone-A) has been synthesised starting from β-resorcylaldehyde which on partial O-prenylation followed by methylation affords the aldehyde (II).The aldehyde (II) on condensation with p-methoxymethoxyacetophenone (III) under alkaline conditions affords the chalcone (IV), which on Claisen rearrangement yields the chalcone (V).Deacetylation and then demethoxymethylation of V by methanolic HCl affords licochalcone-A (VII), identical with a natural sample.