26213-83-2

Usage

InChI:InChI=1/C12H12O4/c1-7-4-9(13)12-10(15-3)5-8(14-2)6-11(12)16-7/h4-6H,1-3H3

Upstream product

• 480-27-3 1-Methyl-3-(2',4',6'-trimethoxyphenyl)propan-1,3-dione 
• 1013-69-0 eugenin 
• 77-78-1 dimethyl sulfate 
• 480-66-0 2,4,6-trihydroxyacetophenone 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 500-99-2 3,5-dimethoxyphenol 
• 121781-82-6 5-(1-methoxyethylene) Meldrum's acid 
• 65547-60-6 1-(2-hydroxy-4, 6-dimethoxyphenyl)butane-1,3-dione 

Downstream Products

• 480-34-2 eugenin 
• 1407546-95-5 C₂₅H₂₈N₂O₄ 
• 1407546-96-6 C₂₄H₂₈N₂O₄ 
• 1382529-04-5 2-[2-(4-(cyclopropylmethoxy)phenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382528-88-2 2-[2-(4-bromophenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382528-89-3 5,7-dimethoxy-2-[2-(4-methoxyphenyl)vinyl]chromen-4-one 
• 1382529-03-4 5,7-dimethoxy-2-[2-(4-nitrophenyl)vinyl]chromen-4-one 
• 1382528-87-1 2-[2-(4-chlorophenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382528-86-0 2-[2-(4-fluorophenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382529-00-1 2-[2-(3,5-dimethoxyphenyl)vinyl]-5,7-dimethoxychromen-4-one 
• 1382529-02-3 5,7-dimethoxy-2-[2-(4-trifluoromethoxyphenyl)vinyl]chromen-4-one 
• 1401428-09-8 (E)-5,7-hydroxy-2-(3,4,5-trihydroxystyryl)-4H-chromen-4-one 
• 1401428-04-3 (E)-5,7-dimethoxy-2-(3,4,5-trimethoxystyryl)-4H-chromen-4-one 

Relevant academic research and scientific papers

TMSI-Promoted vinylogous michael addition of siloxyfuran to 2-substituted chromones: A general approach for the total synthesis of chromanone lactone natural products

A concise and facile synthetic protocol for the construction of the 2-γ-lactone chromanone skeleton has been achieved through a TMSI-promoted diastereoselective vinylogous Michael addition of siloxyfuran to 2-substituted chromones. The applicability of this method is demonstrated through the rapid access to the total syntheses of (±)-microdiplodiasone, (±)-lachnone C, and (±)-gonytolides C and G.

Synthesis and biological evaluation of novel piperazine derivatives of flavone as potent anti-inflammatory and antimicrobial agent

A series of novel 6-methoxy-2-(piperazin-1-yl)-4H-chromen-4-one and 5,7-dimethoxy-2-(piperazin-1-ylmethyl)-4H-chromen-4-one derivatives of biological interest were prepared and screened for their pro-inflammatory cytokines (TNF-α and IL-6) and antimicrobial activity (antibacterial and antifungal). Among all the compound screened (5a-j and 10k-t), the compounds 5c, 5g, 5h, 10l, 10m, 10n and 10r found to have promising anti-inflammatory activity (up to 65-87% TNF-α and 70-93% IL-6 inhibitory activity) at concentration of 10 μM with reference to standard dexamethasone (71% TNF-a and 84% IL-6 inhibitory activities at 1 μM) while the compounds 5b, 5i, 5j, 10s and 10t found to be potent antimicrobial agent showing even 2 to 2.5-fold more potency than that of standard ciprofloxacin and miconazole at the same MIC value of 10 μg/mL.

Synthesis of 2-styrylchromones as a novel class of antiproliferative agents targeting carcinoma cells

A series of 2-styrylchromone analogs were synthesized and examined for their antiproliferative effects on a panel of carcinoma cells. Among the tested agents, only 4m exhibited a moderate activity with an IC50 value of 28.9 μM against PC-3 cells which indicates the selectivity of PC-3 cells in response to 2-styrylchromones. In addition, 4q demonstrated the most antiproliferative effect with an IC50 value of 4.9 μM against HeLa cells. Flow cytometric analysis and DAPI staining revealed that HeLa cells exposed to 4q as low as 5 μM induced cell death through sub-G1 arrest and DNA fragmentation. Furthermore, CoMFA analysis of tested 2-styrylchromones resulted in a q2 of 0.459 to generate a 3D-QSAR model on BT483 cell line. Together, these results suggest a potential structural optimization and pharmacological study of 2-styrylchromones.

Yb(OTf)3-catalyzed reactions of 5-alkylidene Meldrum's acids with phenols: One-pot assembly of 3,4-dihydrocoumarins, 4-chromanones, coumarins, and chromones

The Yb(OTf)3-catalyzed annulation reactions of phenols with 5-alkylidene Meldrum's acids enabled the synthesis of structurally diverse heterocycles in high isolated yields. A series of 4-substituted 3,4-dihydrocoumarins, 2,2-disubstituted 4-chromanones, coumarins, and 2-substituted chromones were readily and efficiently assembled, including the naturally occurring coumarins citropten, scoparone, and ayapin. Addition of phenols to biselectrophilic 5-alkylidene Meldrum's acids proceeded through two distinct multibond-forming modes: Friedel-Crafts C-alkylation/(O-acylation and Friedel-Crafts C-acylation/O-alkylation. The regioselectivity of the catalytic annulation reaction was controlled by the degree of substitution on the alkylidene moiety.