38445-24-8

Upstream product

• 490-78-8 2,5-Dihydroxyacetophenone 
• 109-94-4 formic acid ethyl ester 
• 69155-75-5 6-hydroxy-4-oxo-4H-chromene-3-carbaldehyde 
• 68-12-2 N,N-dimethyl-formamide 
• 123-31-9 hydroquinone 
• 122-51-0 orthoformic acid triethyl ester 
• 51483-92-2 6-bromo-1-benzopyran-4(4H)-one 

Downstream Products

• 59887-88-6 6-methoxy-chromen-4-one 
• 1361926-68-2 6-[(3-methylbenzyl)oxy]-4H-chromen-4-one 
• 1361926-64-8 6-[(3-bromobenzyl)oxy]-4H-chromen-4-one 
• 1361926-60-4 6-(3-phenylpropoxy)-4H-chromen-4-one 
• 1361926-69-3 6-[(4-methylbenzyl)oxy]-4H-chromen-4-one 
• 1361926-59-1 6-(2-phenylethoxy)-4H-chromen-4-one 
• 1361926-65-9 6-[(4-bromobenzyl)oxy]-4H-chromen-4-one 
• 1361926-66-0 6-[(3-fluorobenzyl)oxy]-4H-chromen-4-one 
• 1361926-62-6 6-[(3-chlorobenzyl)oxy]-4H-chromen-4-one 
• 1361926-67-1 6-[(4-fluorobenzyl)oxy]-4H-chromen-4-one 
• 1361926-71-7 4-{[(4-oxo-4H-chromen-6-yl)oxy]methyl}benzonitrile 
• 1361926-72-8 6-{[4-(trifluoromethyl)benzyl]oxy}-4H-chromen-4-one 
• 1361926-70-6 3-{[(4-oxo-4H-chromen-6-yl)oxy]methyl}benzonitrile 
• 80096-64-6 6-hydroxy-2,3-dihydro-4H-chromen-4-one 

Relevant academic research and scientific papers

Synthesis of some new azole, azepine, pyridine, and pyrimidine derivatives using 6-hydroxy-4H-4-oxo[1]-benzopyran-3-carboxaldehyde as a versatile starting material

Condensation of 3-formyl chromone 1 with hydroxylamine hydrochloride afforded the corresponding oxime 2 that was converted to nitrile 3. Refluxing of oxime 2 and/or nitrile 3 with aceturic or hippuric acid gave 16 and 17. Treatment of 1 with semicarbazide hydrochloride and thiosemicarbazide afforded the corresponding carbazones 5-6 that underwent cyclization with ethyl bromoacetate and/or chloroacetone yielding 7-8. Also 1 reacted with acyclic active methylene reagents, e.g. malononitrile, ethyl cyanoacetate, and ethyl acetoacetate to form compounds 11, 12, and 13. Reaction of 1 with bifunctional reagents, e.g. benzil, o-phenylenediamine, o-aminophenol, and o-aminothiophenol yielding the corresponding imidazolyl bezopyranone and azepine derivatives 14-20. Condensation of 1 with acyclic or heterocyclic compounds containing active methylene group, e.g. hippuric acid forming the condensed products 21-27.

Synthesis and evaluation of trypanocidal activity of chromane-type compounds and acetophenones

American trypanosomiasis (Chagas disease) caused by the Trypanosoma cruzi parasite, is a severe health problem in different regions of Latin America and is currently reported to be spreading to Europe, North America, Japan, and Australia, due to the migration of populations from South and Central America. At present, there is no vaccine available and chemotherapeutic options are reduced to nifurtimox and benznidazole. Therefore, the discovery of new molecules is urgently needed to initiate the drug development process. Some acetophenones and chalcones, as well as chromane-type substances, such as chromones and flavones, are natural products that have been studied as trypanocides, but the relationships between structure and activity are not yet fully understood. In this work, 26 compounds were synthesized to determine the effect of hydroxyl and isoprenyl substituents on trypanocide activity. One of the compounds showed interesting activity against a resistant strain of T. cruzi, with a half effective concentration of 18.3 μM ± 1.1 and an index of selectivity > 10.9.

NOVEL USE OF SUBSTITUTED CHROMAN-6-OLS

The present invention is directed towards the use of substituted chroman-6-ols of formula (I) wherein R1 and R2 are independently from each other H or C1-11-alkyl or (CH2)n—OH with n being an integer

Discovery of 4 H-Chromen-4-one Derivatives as a New Class of Selective Rho Kinase (ROCK) Inhibitors, which Showed Potent Activity in ex Vivo Diabetic Retinopathy Models

Diabetic retinopathy (DR) is a major cause of blindness, and there is a lack of effective treatment at present. Rho-associated coiled-coil containing serine/threonine protein kinases (ROCKs) have recently been suggested as potential targets for the DR treatment. We herein report the discovery of 4H-chromen-4-one derivatives as a new class of ROCK inhibitors. Structure-activity relationship analyses led to the identification of the most active compound, 4-(dimethylamino)-N-(3-{2-[(4-oxo-4H-chromen-7-yl)oxy]acetamido}phenyl) (12j). This compound showed excellent kinase selectivity for ROCK I and ROCK II against 387 other kinases. In retinal explants, compound 12j protected retinal neurons from high glucose-induced oxidative stress and apoptosis-mediated cell death. Furthermore, 12j administration suppressed the improper proliferation of Müller cells and promoted the regression of vascular vessels in retinal explants cultured in a high glucose microenvironment. Collectively, our data suggest that 12j could be a potential lead compound for the treatment of DR, hence deserving further in-depth studies.

Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water

A highly effective hydroxylation reaction of aryl halides with water under synergistic organophotoredox and nickel catalysis is reported. The OH group of the resulting phenols originates from water, following deprotonation facilitated by an intramolecular base group on the ligand. Significantly, aryl bromides as well as less reactive aryl chlorides served as effective substrates to afford phenols with a wide range of functional groups. Without the need for a strong inorganic base or an expensive noble-metal catalyst, this process can be applied to the efficient preparation of diverse phenols and enables the hydroxylation of multifunctional pharmaceutically relevant aryl halides.

Synthesis, antiproliferative, and c-Src kinase inhibitory activities of 4-oxo-4H-1-benzopyran derivatives

A new class of 4-oxo-4H-1-benzopyran derivatives were synthesized and their antiproliferative activity examined against a panel of three human cancer cell lines, that is, breast carcinoma (MDA-MB-468), ovarian adenocarcinoma (SK-OV-3), and colorectal adenocarcinoma (HT-29). Two compounds, that is, 3-hexyl-7,8-dihydroxy-4-oxo-4H-1-benzopyran and (E)-ethyl 3-(7-methoxy-4-oxo-4H-1-benzopyran-3-yl)acrylate were found to be potent against all three cancer cell lines studied at 50 μM concentration. Also, the inhibitory potency of the compounds was evaluated against active Src kinase. A few of these compounds exhibited modest Src kinase inhibitory activity (IC50 = 52-57 μM). Structure-activity relationship studies with respect to the nature and position of substituents on the lead compounds could be further exploited for the design and development of more potent antiproliferative agents and/or Src kinase inhibitors.

Behaviour of o-hydroxyacetophenones towards action of POCl3/DMF (Vilsmeier reagent) in presence of BF3.Et2O: A novel observation in the synthesis of chromones

The influence of the presence of BF3.Et2O on the Vilsmeier reactions of o-hydroxyacetophenones and related naphthophenones has been examined. A significant and novel feature of this study is the development of new and facile procedure for the synthesis of some chromones. The reaction offers a first example of monoformylation of o-hydroxyacetophenones.

Dopamine autoreceptor agonists as potential antipsychotics. 2. (Aminoalkoxy)-4H-1-benzopyran-4-ones

The synthesis and pharmacological properties of a novel type of [(arylpiperazinyl)alkoxy]-4H-1-benzopyran-4-ones with dopaminergic activity are described. The nature of the arylpiperazine (AP) moiety determines the dopamine (DA) agonist/antagonist character of this series of compounds; when the aryl portion of the AP is unsubstituted the compounds appear to be DA autoreceptor agonists while substituted aryl groups seem to impart DA antagonist activity. A heterocyclic piperazine, 7-[3-[4-(2-pyridinyl)-1-piperazinyl]propoxy]-4H-1-benzopyran-4-one (31, PD 119819) has been identified as an extremely selective DA autoreceptor agonist in tests that include [3H]haloperiodol binding, inhibition of spontaneous locomotor activity, inhibition of brain DA synthesis, inhibition of brain DA neuronal firing, stereotypy assessment, and reversal of 6-hydroxydopamine (6-OHDA) induced akinesia in rats. In addition, 31 possesses good oral activity in the Sidman avoidance test in squirrel monkeys, a predictor of clinical antipsychotic efficacy. In another primate model, 31 has been found to lack the liability for extrapyramidal side effects observed with currently available antipsychotic drugs.