55977-30-5

Upstream product

• 90-02-8 salicylaldehyde 
• 16636-62-7 1-(2'-hydroxyphenyl)butane-1,3-dione 
• 5751-48-4 2-methylchromone 
• 104-88-1 4-chlorobenzaldehyde 
• 205308-00-5 (E)-3-(4-Chloro-phenyl)-acrylic acid 2-acetyl-phenyl ester 
• 1615-02-7 3-(4-chlorophenyl)prop-2-enoic acid 
• 118-93-4 o-hydroxyacetophenone 
• 205308-03-8 (2Z,4E)-5-(4-Chloro-phenyl)-3-hydroxy-1-(2-hydroxy-phenyl)-penta-2,4-dien-1-one 
• 133567-72-3 1-p-Chlorophenyl-4-(o-hydroxybenzoyl)-(1E,3E)-butadiene 

Downstream Products

• 1522165-50-9 C₂₀H₁₃ClN₂O₂ 
• 1522165-59-8 C₂₀H₁₃ClN₂O₂ 
• 1522165-41-8 C₂₄H₂₃ClO₆ 
• 1451210-45-9 5-(4-chlorophenyl)-4-[3-(2-hydroxyphenyl)-1H-pyrazol-5-yl]-1H-1,2,3-triazole 
• 1354549-07-7 C₁₈H₁₄ClNO₄ 
• 1000997-11-4 2-[3-(4-chlorophenyl)-1,2,3,4-tetrahydronaphth-2-yl]chromone 
• 223509-37-3 (Z)-4'-chloro-2-(α-bromostyryl)chromone 

Relevant academic research and scientific papers

Rh-Catalyzed aldehydic C-H alkynylation and annulation

Novel Rh-catalyzed aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-

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.

Synthesis of (E)-2-styrylchromones and flavones by base-catalyzed cyclodehydration of the appropriate β-diketones using water as solvent

A low cost, safe, clean and environmentally benign base-catalyzed cyclodehydration of appropriate β-diketones affording (E)-2-styrylchromones and flavones in good yields is disclosed. Water was used as solvent and the reactions were heated using classical

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.

(E)-3-Halo-2-styryl-4H-chromen-4-ones: Synthesis and transformation to novel pyrazoles

New methods for the synthesis of (E)-3-halo-2-styryl-4H-chromen-4-ones were established. The reaction of these compounds with hydrazine hydrate afforded new and unexpected 3(5)-aryl-5(3)-[2-(2-hydroxyphenyl)-2-hydrazonoethyl]-1H- pyrazoles, which upon aci

(E)-2-Styrylchromones as potential anti-norovirus agents

Human noroviruses (NoV) are now recognized as the most frequent cause of outbreaks and sporadic cases of acute gastroenteritis. Despite the significant economic impact and considerable morbidity of norovirus disease, no drug or vaccine is currently available to treat or prevent this disease, therefore the discovery of anti-norovirus drugs is urgent. In the present work, a total of 12 structure related chromone and (E)-2-styrylchromones were evaluated for their potential anti-norovirus activity using the murine norovirus (MNV) as a surrogate model for human NoV. From the 12 compounds studied, six (E)-2-styrylchromones were found to have with interesting anti-norovirus activity. The best compounds of the series were (E)-5-hydroxy-2-styrylchromone and (E)-4′-methoxy-2-styrylchromone with an IC50 ≈ 7 μM. A first insight into the mechanism of action of these compounds was possible. An interesting relationship between the anti-norovirus activity and the chemical structure was observed. The present study points out that the (E)-2-styrylchromones skeleton is an important one which deserves to be developed and further explored as new antiviral drugs against NoV.

Synthesis of 4-Aryl-3-(2-chromonyl)-2-pyrazolines by the 1,3-Dipolar Cycloaddition of 2-Styrylchromones with Diazomethane

The first reported 1,3-dipolar cycloaddition of 2-styrylchromones with diazomethane afforded 4-aryl-3-(2-chromonyl)-2-pyrazolines. However, 3-aryl-4-(2-chromonyl)-1-pyrazolines have been also found as minor products of this reaction. These two series of p

Novel (E)- and (Z)-2-styrylchromones from (E,E)-2′-hydroxycinnamylideneacetophenones - Xanthones from daylight photooxidative cyclization of (E)-2-styrylchromones

The oxidative cyclization of (E,E)-2′-hydroxycinnamylideneacetophenones 1a-e, and (E,E)-2′-benzyloxy-6′-hydroxycinnamylideneacetophenones 1i-1 with DMSO/ iodine, gave (E)-2-styrylchromones 3a-e,i-1. However, in the case of (E,E)-γ-alkyl-2′-hydroxycinnamyl

Synthesis of (E)-2-Styrylchromones

A new synthesis of (E)-2-styrylchromones has been developed in paralell with synthetic studies on several flavone derivatives.