93176-02-4

Upstream product

• 57544-06-6 6-methoxy-2-(4-methoxyphenyl)-3-nitro-2H-chromene 
• 114021-51-1 (2E)-1-(2-hydroxy-5-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 
• 54401-48-8 C₁₇H₁₆O₄ 
• 123-11-5 4-methoxy-benzaldehyde 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 

Downstream Products

• 111391-77-6 3,6-dimethoxy-2-(4-methoxy-phenyl)-chromen-4-one 
• 1242087-52-0 3-Hydroxy-6,4'-dimethoxyflavone 3-glucuronide 

Relevant academic research and scientific papers

Exploring the anti-breast cancer potential of flavonoid analogs

In the course of our search for new antitumor agents for breast cancer, novel flavone derivatives were synthesized, characterized and examined for their antitumor activities against breast cancer cell lines. In initial screening, analogs 7a [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-phenyl-4H-chromen-4-one] and 7b [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one] were found to be effective against the estrogen receptor negative cell line (MDA-MB 453), which was followed by their evaluation in five dose assays. In addition, mechanistic studies of 7a and 7b were performed by cytometric analysis and electrophoretic studies and it was observed that apoptosis is a mechanism of cell death, confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis. Further in vivo evaluation of the anti-tumor activity of compound 7a and 7b by Ehrlich Ascites Carcinoma (EAC) model and related studies confirms the anti-breast cancer potential of flavonoid analogs.

Profiling of flavonol derivatives for the development of antitrypanosomatidic drugs

Flavonoids represent a potential source of new antitrypanosomatidic leads. Starting from a library of natural products, we combined target-based screening on pteridine reductase 1 with phenotypic screening on Trypanosoma brucei for hit identification. Flavonols were identified as hits, and a library of 16 derivatives was synthesized. Twelve compounds showed EC50 values against T. brucei below 10 μM. Four X-ray crystal structures and docking studies explained the observed structure-activity relationships. Compound 2 (3,6-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one) was selected for pharmacokinetic studies. Encapsulation of compound 2 in PLGA nanoparticles or cyclodextrins resulted in lower in vitro toxicity when compared to the free compound. Combination studies with methotrexate revealed that compound 13 (3-hydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one) has the highest synergistic effect at concentration of 1.3 μM, 11.7-fold dose reduction index and no toxicity toward host cells. Our results provide the basis for further chemical modifications aimed at identifying novel antitrypanosomatidic agents showing higher potency toward PTR1 and increased metabolic stability.

4'-Hydroxy-3-methoxyflavones with potent antipicornavirus activity

4'-Hydroxy-3-methoxyflavones are natural compounds with known antiviral activities against picornaviruses such as poliomyelitis and rhinoviruses. In order to establish a structure-activity relationship a series of analogues were synthesized, and their antiviral activities and cytotoxicities were compared with those of flavones from natural origin. The 4'-hydroxyl and 3-methoxyl groups, a substitution in the 5 position and a polysubstituted A ring appeared to be essential requirements for a high activity. The most interesting compound was 4',7-dihydroxy-3-methoxy-5,6-dimethylflavone possessing in vitro TI99 values of > 1000 and > 200 against poliovirus type 1 and rhinovirus type 15, respectively. This compound was also active against other rhinovirus serotypes (2, 9, 14, 29, 39, 41, 59, 63, 70, 85, and 89) tested, having MIC50 values ranging from 0.016 to 0.5 μg/mL. Finally in contrast to quercetin it showed to be not mutagenic in concentrations up to 2.5 mg in the Ames test.

A NOVEL SYNTHESIS OF 6-METHOXY AND 7-METHOXY FLAVONOLS

Condensation of 4-methoxy- (1) or 5-methoxy- (2) salicylaldehyde with ω-nitrostyrene (3-6) in the presence of triethylamine yields 7-methoxy or 6-methoxy-3-nitro-2H-flavene (7-13), which on treatment with alkaline hydrogen peroxide yields the correspondin

REACTION OF CHROMOUS CHLORIDE WITH 3-NITROFLAVENES. A NOVEL SYNTHESIS OF FLAVONOLS

Reaction of Chromium(II) chloride with 3-nitroflavene yields flavonol.