62018-55-7

Usage

Preparation

Obtained by reaction of acetonitrile with 2,4,6-trihydroxy-benzaldehyde (Houben-Hoesch reaction) Also obtained by reaction of ethyl orthoformate with phloracetophenone in the presence of aluminium chloride Preparation by adding successively zinc cyanide and aluminium chloride to a solution of phloracetophenone in ethyl ether. The reaction mixture was cooled in ice and saturated with hydrogen chlorideAlso obtained by reaction of DMF with phloracetophenone in the presence of phosphorous oxychloride at 20° for 1 h (70%).

Upstream product

• 480-66-0 2,4,6-trihydroxyacetophenone 
• 122-51-0 orthoformic acid triethyl ester 
• 108-73-6 3,5-dihydroxyphenol 
• 7647-01-0 hydrogenchloride 
• 7446-70-0 aluminium trichloride 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 2657-28-5 2,4,6-trihydroxy-3-methyl-acetophenon 
• 140170-46-3 8-acetyl-3,4-dihydro-5,7-dihydroxy-6-methyl-4-(4-hydroxyphenyl)coumarin 
• 140170-45-2 6-acetyl-3,4-dihydro-5,7-dihydroxy-8-methyl-4-(4-hydroxyphenyl)coumarin 
• 140170-47-4 methyl 3-(5-acetyl-2,3,4-trihydroxy-3-methyl-6-oxo-1,4-cyclohexadienyl)-3-(4-hydroxyphenyl)propanoate 
• 140170-48-5 methyl 3-(5-acetyl-3,4-dihydroxy-2-methoxy-3-methyl-6-oxo-1,4-cyclohexadienyl)-3-(4-hydroxyphenyl)propanoate 
• 140170-51-0 3-<2,3,4-trihydroxy-5-(4-hydroxycinnamoyl)-3-methyl-6-oxo-1,4-cyclohexadienyl>-3-(4-hydroxyphenyl)propanoic acid 
• 140170-50-9 methyl 3-<2,3,4-trihydroxy-5-(4-hydroxycinnamoyl)-3-methyl-6-oxo-1,4-cyclohexadienyl>-3-(4-hydroxyphenyl)propanoate 
• 140170-49-6 methyl 3-<3,4-dihydroxy-5-(4-hydroxycinnamoyl)-2-methoxy-3-methyl-6-oxo-1,4-cyclohexadienyl>-3-(4-hydroxyphenyl)propanoate 
• 59677-81-5 3-acetyl-2,4,6-trihydroxy-5-methylbenzaldehyde 

Relevant academic research and scientific papers

The Mosaic of Rottlerin

The first total synthesis of rottlerin is described. The methodology allows the development of potential novel protein kinase C δ (PKCδ) analogues for better treatment of various diseases. Kamalachalcone A and dimeric rottlerin were synthesized in a very

Concise synthesis and cellular evaluation of 3′-formyl-4′,6′-dihydroxy-2′-methoxy-5′-methylchalcone (FMC) and its analogues

3′-Formyl-4′,6′-dihydroxy-2′-methoxy-5′-methylchalcone (FMC) was a natural product isolated from Cleistocalyx operculatus. A four-step synthetic strategy toward FMC and its four analogues (1b-1e) was first developed. All compounds were synthesized from commercially available 2,4,6-trihydroxyacetophenone; formylation at 3′ position under Vilsmeier-Haack conditions was followed by the introduction of a methyl group at 5′ position. The key step of selective methylation at 2′ position was achieved by trimethylsilyldiazomethane (TMSCHN2). Then substituted aromatic aldehydes were condensed through Claisen-Schmidt reaction in the presence of potassium hydroxide. All structures were confirmed by 1H NMR, 13C NMR, and high-resolution mass spectra. FMC and analogues were screened for their antiproliferative activity.

Biomimetic synthesis, antimicrobial, antileishmanial and antimalarial activities of euglobals and their analogues

In the present communication, naturally occurring phloroglucinol- monoterpene adducts, euglobals G1-G4 (3b/a and 4a/b) and 16 new analogues (13a/b-18a/b and 19-22) were synthesized by biomimetic approach. These synthetic compounds differ from natural euglobals in the nature of monoterpene and acyl functionality. All of these compounds were evaluated for their antibacterial, antifungal, antileishmanial and antimalarial activities. Analogue 17b possessed good antibacterial activity against methicillin-resistant Staphylococcus aureus, while analogues 19-22 possessed potent antifungal activity against Candida glabrata with IC50s ranging from 1.5 to 2.5 μg/mL. Euglobals along with all synthesized analogues exhibited antileishmanial activity. Amongst these, euglobal G2 (3a), G3 (4a) and analogues 13a and 14a showed potent antileishmanial activity with IC50s ranging from 2.8 to 3.9 μg/mL. Analogue 16a possessed antimalarial activity against chloroquine sensitive D6 clone of Plasmodium falciparum. None of the compounds showed toxicity against mammalian kidney fibroblasts (vero cells) upto the concentration of 4.76 μg/ml.

An efficient two-step synthesis of jensenone isolated from Eucalyptus jensenii. Synthesis of analogues and evaluation as antioxidants

A phloroglucinol derivative, jensenone (1) isolated from leaves of Eucalyptus jensenii has been synthesized for the first time through a short and efficient two-step procedure starting from commercially available phloroglucinol. The methodology provides a simplified route to introduce diformyl moiety for synthesis of biologically active formylated phloroglucinol compounds such as antimalarial robustadials, cancer chemopreventive euglobals, and antifouling sideroxylonals. Several analogues of jensenone have also been synthesized and evaluated for antioxidant capacity. CSIRO 2005.

Structure/Activity relationships of Grandinol: a Germination Inhibitor in Eucalyptus

Structure/activity relationships of grandinol (1), which shows potent inhibition to cress germination, were examined by an activity comparison of many synthetic analogues.The result clearly indicates that a combination of two carbonyl functionalities on a