49619-59-2

Upstream product

• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 68-12-2 N,N-dimethyl-formamide 
• 699-83-2 2,6-dihydroxylacetophenone 
• 79-37-8 oxalyl dichloride 

Downstream Products

• 1307915-51-0 9-methoxy-10-oxo-3-phenyl-4a,10-dihydropyrano[4,3-b]chromene-4-carbaldehyde 
• 1448991-92-1 dimethyl 3-(2-hydroxy-6-methoxybenzoyl)-6,7,12,12b-tetrahydroindolo[2,3-a]quinolizine-1,12b-dicarboxylate 
• 1422452-73-0 (E)-5-methoxy-3-(3-(4-(4-methoxybenzyloxy)phenyl)-3-oxoprop-1-enyl)-4H-chromen-4-one 
• 1422452-59-2 (E)-3-(3-hydroxy-3-(4-hydroxyphenyl)prop-1-enyl)-5-methoxy-4H-chromen-4-one 
• 1422452-47-8 (E)-3-(3-(4-hydroxyphenyl)-3-oxoprop-1-enyl)-5-methoxy-4H-chromen-4-one 
• 1160309-63-6 (E)-5-methoxy-3'-nitro-3-styrylchromone 

Relevant academic research and scientific papers

Synthesis of Chromeno[2,3-d]pyrimidin-5-one Derivatives from 1,3,5-Triazinanes via Two Different Reaction Pathways

1,3,5-Triazinanes, as a kind of versatile building block, are applied in the synthesis of chromeno[2,3-d]pyrimidin-5-one derivatives via two different reaction modes, which perfectly exhibits the powerful function of 1,3,5-triazinane as a three-atom synth

One pot and metal-free approach to 3-(2-Hydroxybenzoyl)-1-aza-anthraquinones

Herein, a direct strategy to synthesize 3-(2-hydroxybenzoyl)-1-aza-anthraquinones with excellent efficiency,mild conditions, and benign functional group compatibilitywas reported. Avariety of 3-formylchromone compounds were employed as compatible substrates and this protocol gave the 3-(2-hydroxybenzoyl)-1-aza-anthraquinone derivatives in good to excellent yields without inert gas and expensive transition metal catalysts. Some compounds displayed good anti-proliferative activities.

Synthesis and biological evaluation of N-Aryl-N′-(5-(2-hydroxybenzoyl) pyrimidin-2-yl)guanidines as toll-like receptor 4 antagonists

Background: Toll-like receptor 4 (TLR4) has been associated with several inflammatory diseases, such as sepsis, atherosclerosis and chronic pain. Objective: The aim of the present study was to develop an efficient and straightforward synthetic approach for the preparation of small-molecule antagonists Naryl-N′-(5-(2-hydroxybenzoyl)pyrimidin-2-yl)guanidines in order to evaluate these for TLR4 antagonist activity and to obtain useful information about their structure-activity relationships. Methods: The present work have designed and optimized a three-step synthetic route for derivatives of a previously demonstrated antagonist of TLR4: 1-(4-fluorophenyl)-2-(5-(2-hydroxy-5-methoxybenzoyl)pyrimidin-2-yl)guanidine. The antagonist activities of eight novel synthesized compounds were evaluated on cells which selectively express TLR4. Results: Three guanidine derivatives showed promising antagonist activities, with IC50 values in the low micromolar range. Conclusion: Our findings represent an important starting point for further studies of small-molecule agents targeting Toll-like receptors.

Direct construction of xanthene and benzophenone derivatives via Br?nsted acid controlled Diels-Alder reaction of 3-vinylchromones and arynes

A Br?nsted acid controlled Diels-Alder reaction of 3-vinylchromones with arynes has been developed. By employing different kinds and amounts of acid, 9-aryl-9H-xanthen-9-ols or ortho-hydroxybenzophenones could be controllably furnished in good yields in an atom- and step-economic manner.

Thiazolidine-2,4-diones derivatives as PPAR-γ agonists: Synthesis, molecular docking, in vitro and in vivo antidiabetic activity with hepatotoxicity risk evaluation and effect on PPAR-γ gene expression

A library of conjugates of chromones and 2,4-thiazolidinedione has been synthesized by Knoevenagel condensation followed by reduction using hydrogen gas and Pd/C as a catalyst. Compounds 5c and 5e were most effective in lowering the blood glucose level comparable to standard drug pioglitazone. Compound 5e exhibited potent PPAR-γ transactivation of 48.72% in comparison to pioglitazone (62.48%). All the molecules showed good glide score against the PPAR-γ target in molecular docking study. PPAR-γ gene expression was significantly increased by compound 5e (2.56-fold) in comparison to standard drug pioglitazone. Compounds 5e and 5c did not cause any damage to the liver and may be considered as promising candidates for the development of new antidiabetic agents.

Identification of novel chromenone derivatives as interleukin-5 inhibitors

A series of (E)-5-alkoxy-3-(3-phenyl-3-oxoprop-1-enyl)-4H-chromen-4-ones (4) and (E)-5-alkoxy-3-(3-hydroxy-3-phenylprop-1-enyl)-4H-chromen-4-ones (5) were synthesized and evaluated for their IL-5 inhibitory activity. Propenone analogs 4 possess some of the structurally important characteristics of isoflavone 2 and chalcone 3 previously known as potent IL-5 inhibitor. However, the inhibitory activity of 4 was weak and therefore this structural hybridization appears to be ineffective for the design of IL-5 inhibitor. Meanwhile the potent activity profile of compounds 5 was discovered. This enhanced activity of 5 compared to 4 could be due to the effective location of hydroxyl group of allylic alcohol moiety of 5 in the 3D structure. The electron withdrawing substituents at position 4 of phenyl ring of 5 enhances the activity possibly due to an increase in the strength of hydrogen bonding property of hydroxyl group of allylic alcohol moiety.

Novel benzofuran-chromone and -coumarin derivatives: Synthesis and biological activity in K562 human leukemia cells

Not widely distributed in nature, aurones, (Z)-2-benzylidene-benzofuran- 3(2H)-ones, are one of the less common and lesser-known representatives of a flavonoid subclass. Nevertheless, they exhibit a strong and broad variety of biological activities. We have combined the benzofuranone part of a classical aurone with either a chromone or a coumarin scaffold which proved to feature interesting biological activities including antimicrobial, antiviral, anticancer, anti-inflammatory and antioxidant properties. Herein we present a series of 26 novel benzofuran derivatives with the first biological results in K562 human leukemia cells showing that compounds 21b, 29b and 29c are able to induce around 24% apoptosis.

Lewis base catalyzed [4+2] annulation of electron-deficient chromone-derived heterodienes and acetylenes

Lewis base catalyzed [4+2] annulation reactions between electron-deficient chromone oxa- and azadienes and acetylene carboxylates provide tricyclic benzopyrones inspired by natural products. An asymmetric synthesis of the tricyclic benzopyrones was developed by using modified cinchona alkaloids as enantiodifferentiating Lewis base catalysts.

Diels-Alder reactions of chromone-3-carboxaldehydes with ortho-benzoquinodimethane. New synthesis of benzo[b]xanthones

An efficient new route to the benzo[b]xanthone system has been developed and applied to the synthesis of several new derivatives. The cycloaddition reactions of chromone-3-carboxaldehydes 12, reacting as dienophiles, with ortho-benzoquinodimethane 7 gave a diastereomeric mixture of cycloadducts 8 and 9. The formation of these compounds results from the Diels-Alder reactions of 12 and 7 followed by the in situ deformylation. The oxidation of adducts 8 and 9 with dimethyl sulfoxide in the presence of iodine gave the novel benzo[b]xanthones 11 in good yields.

Chromonealdehyde compounds and process for the production thereof

There are provided compounds of the general formula SPC1 Wherein R is a hydroxy, alkyl, acyloxy, halogen, nitro, substituted or unsubstituted amino, alkoxy, carboxy or a group derived from a carboxy group and m is 0, 1 or 2 except where m is 2, the two R groups are both hydroxy groups. The present invention is also concerned with a process for preparing the chromonealdehyde compounds. The chromonealdehyde compounds are characterized by antiallergic properties and are therefore useful as prophylactic and therapeutic agents for allergic asthma, allergic dermatitis and other allergic diseases and also are valuable as intermediates for the synthesis of other pharmaceutical compounds having the chromone nucleus.