80212-23-3

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-
• CAS NO: 80212-23-3
• Molecular Formula: C19H16O4
• Molecular Weight: 308.334
• Mol File: 80212-23-3.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-(80212-23-3)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 2-[2-(3,4-dimethoxyphenyl)ethenyl]-(80212-23-3)

Safety Data

• Hazardous Substances Data: 80212-23-3(Hazardous Substances Data)

Upstream product

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Relevant articles and documents

SYNTHESIS AND ANTIALLERGIC ACTIVITY OF NOVEL CHROMONE DERIVATIVES

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2-Styrylchromone derivatives as potent and selective monoamine oxidase B inhibitors

A series of eighteen 2-styrylchromone derivatives (see Chart 1) were synthesized and evaluated for their monoamine oxidase (MAO) A and B inhibitory activities. Many of the derivatives inhibited MAO-B comparable to pargyline (a positive control), and most of them inhibited MAO-B selectively. Of the eighteen derivatives, compound 9 having methoxy group at R1 and chlorine at R4 showed both the best MAO-B inhibitory activity (IC50 = 17 ± 2.4 nM) and the best MAO-B selectivity (IC50 for MAO-A/IC50 for MAO-B = 1500). The mode of inhibition of compound 9 against MAO-B was competitive and reversible. Quantitative structure–activity relationship (QSAR) analyses of the 2-styrylchromone derivatives were conducted using their pIC50 values with the use of Molecular Operating Environment (MOE) and Dragon, demonstrating that the descriptors of MAO-B inhibitory activity and MAO-B selectivity were 1734 and 121, respectively, that showed significant correlations (P 50 value indexes for MAO-B exhibited a determination coefficient (R2) of 0.873 as well as a Leave-One-Out cross-validated determination coefficient (Q2) of 0.675. These data suggested that the 2-styrylchromone structure might be a useful scaffold for the design and development of novel MAO-B inhibitors.

Structure-activity relationship study of growth inhibitory 2-styrylchromones against carcinoma cells

The structure-activity relationship study of 2-styrylchromones against carcinoma cell growth is discussed in the present report. Taking advantage of 2-styrylchromone as a molecular template, a series of structural modifications was carried out and examined on several carcinoma cell lines. Interestingly, AGS cells exhibited more sensitivity in response to methoxy-bearing compounds, of which compound 23 (3,4,5-trimethoxy group on ring B) showed the most potent activity with a GI50 value of 1.3 μM. Surprisingly, as methoxy groups in 12 and 24-27 were demethylated to generate their hydroxyl counterparts 28-32, none of them displayed appreciable activity against all carcinoma cells. We further confirmed the pivotal role of rigidity for growth inhibitory activity between the rigid 12 and its flexible counterpart 33. Taken together, in the present report, we have clearly demonstrated the structure-activity relationship study of 2-styrylchromones targeting carcinoma cell growth.