17771-33-4

Usage

Uses

Used in Pharmaceutical and Nutraceutical Industries:
7-HYDROXY-2,2-DIMETHYL-CHROMAN-4-ONE serves as an antioxidant agent for its capacity to mitigate oxidative stress and inflammation, which are implicated in the pathogenesis of numerous diseases such as cancer, cardiovascular diseases, and neurodegenerative disorders. Its protective role against cellular damage positions it as a potential therapeutic agent in these areas.
Used in Antioxidant Research:
In the scientific community, 7-HYDROXY-2,2-DIMETHYL-CHROMAN-4-ONE is utilized as a benchmark compound in studies assessing antioxidant capabilities. Its well-defined properties make it an ideal standard for comparing the efficacy of novel antioxidants.
Used in Food Industry:
7-HYDROXY-2,2-DIMETHYL-CHROMAN-4-ONE is employed as a food additive to extend the shelf life of products. Its antioxidant properties help in preserving food items by preventing the oxidative spoilage that can lead to rancidity and other forms of degradation, ensuring freshness and quality over a longer period.

InChI:InChI=1/C11H12O3/c1-11(2)6-9(13)8-4-3-7(12)5-10(8)14-11/h3-5,12H,6H2,1-2H3

Upstream product

• 107054-41-1 7-hydroxy-2,2-dimethyl-4-oxo-chroman-6-carboxylic acid 
• 3350-78-5 3,3-Dimethylacryloyl chloride 
• 108-46-3 recorcinol 
• 541-47-9 3-Methylbutenoic acid 
• 67716-21-6 3-bromo-3-methyl-butyryl chloride 
• 99323-00-9 1-(2',4'-dihydroxyphenyl)-3-methyl-but-2-en-1-one 
• 37637-88-0 N-formamido-3-methyl-2-butenamide 
• 100942-29-8 2,2-dimethyl-4-keto-7-tosyloxy-benzopyran 
• 10025-91-9 antimony(III) chloride 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 67-64-1 acetone 
• 20321-73-7 7-methoxy-2,2-dimethyl-4-chromanone 
• 17598-02-6 2,2 dimethyl 7 methoxychromene 
• 20052-58-8 7-methoxy-2,2-dimethyl-3,4-dihydro-2H-1-benzopyran 

Downstream Products

• 59257-86-2 7-(benzyloxy)-2,2-dimethylchroman-4-one 
• 102026-85-7 7-hydroxy-2,2-dimethyl-chroman-4-one-(2,4-dinitro-phenylhydrazone) 
• 115613-80-4 2,2-Dimethyl-7-propoxy-chroman-4-one 
• 120046-19-7 7-Cyclohexyloxy-2,2-dimethyl-chroman-4-one 
• 133035-34-4 N-(2,6-Diethyl-phenyl)-2-(2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide 
• 128890-27-7 N-(3-Chloro-phenyl)-2-(2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide 
• 128890-30-2 N-(3-Bromo-phenyl)-2-(2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide 
• 128890-29-9 N-(2-Bromo-phenyl)-2-(2,2-dimethyl-4-oxo-chroman-7-yloxy)-acetamide 
• 133035-33-3 2-(2,2-Dimethyl-4-oxo-chroman-7-yloxy)-N-(2-ethyl-6-methyl-phenyl)-acetamide 
• 131859-59-1 2-(2,2-Dimethyl-4-oxo-chroman-7-yloxy)-N-phenyl-propionamide 
• 131859-60-4 2-(2,2-Dimethyl-4-oxo-chroman-7-yloxy)-N-phenyl-butyramide 
• 120046-23-3 7-((4-chlorobenzyl) oxy)-2,2-dimethylchroman-4-one 
• 120046-22-2 7-(2-Chloro-benzyloxy)-2,2-dimethyl-chroman-4-one 
• 144537-17-7 7-cyanomethoxy-2,2-dimethyl-4-chromanone 

Relevant academic research and scientific papers

Modified coumarins. 32. Synthesis of amino-acid derivatives of dihydropyranocoumarins

Linear dihydropyranocoumarins containing natural and synthetic amino acids were synthesized using activated esters.

Modified coumarins. 13. Synthesis of cyclopentane-annelated pyranocoumarins

Modified pyranocoumarins containing a condensed cyclopentane fragment were synthesized by adjoining a 2,2-dimethyltetrahydropyran ring to a 2,3-dihydrocyclopenta[c]chromen-4-one system and annelation of a pyrone ring to a 2,2-dimethylchromane.

Design, synthesis and biological evaluation of novel benzoxaborole derivatives as potent PDE4 inhibitors for topical treatment of atopic dermatitis

In this work, a series of structurally novel benzoxaborole derivatives were designed, synthesized and biologically evaluated as PDE4 inhibitors for battling atopic dermatitis (AD). Among them, the majority exhibited superior PDE4B inhibitory activities to that of the lead compound Crisaborole, an approved PDE4 inhibitor. In particular, 72, the most potent PDE4B inhibitor throughout this series, displayed 136-fold improved enzymatic activity (IC50 = 0.42 nM) as compared to Crisaborole (IC50 = 57.20 nM), along with favorable isoform specificity. In the phorbol ester (PMA)-induced mouse ear oedema model, 72 exerted remarkably greater efficacy than Crisaborole at the same dosage (P 0.05). Moreover, the ointment of 72 exerted dramatically enhanced therapeutic potency than the ointment of Crisaborole (P 0.05) in the calcipotriol-induced mouse AD model. In addition to the potent in vitro and in vivo activity, 72 displayed favorable safety in the repeated oral dose toxicity study and did not exhibit phototoxicity. With the above attractive biological performance, 72 is worthy of further functional investigation as a novel anti-AD therapeutic agent.

Synthesis and biological evaluation of substituted amide derivatives of C4-ageratochromene dimer analog

Substituted amide derivatives of C4-ageratochromene dimer analog (19) were synthesized through structural modification of precocene-I (4a), isolated from the essential oil of Ageratum conyzoides L. The target compounds (18–20, 23I-VI, 24I-VI, and 25I-VI) were evaluated for their bone-forming effect using osteoblast differentiation assay. Seven compounds (23I, 23II, 23IV, 23VI, 24III, 24VI, and 25VI) presented good activity within 1 pM–1 nM concentration. At 1 pM concentration, the most active compound i.e. 23II showed effective mineralization of osteoblast cells along with expression of osteogenic marker genes viz RUNX 2, BMP-2, and type 1 collagen (Type-1 col) without any toxicity towards osteoblast cells. Single crystal X-ray analysis of 18 and 20 revealed that the core nucleus of these molecules bear phenyl rings in a Trans-stilbenoid system and had a good structural correlation with 17β-estradiol (1) and diethylstilbestrol (DES, 3). In-silico study about 23II showed its structural complementarities with the LBD of estrogen receptor (ER) which indicated possible ER-mediated activity of compounds.

Design and structural optimization of novel 2H-benzo[h]chromene derivatives that target AcrB and reverse bacterial multidrug resistance

Drug efflux pumps have emerged as a new drug targets for the treatment of bacterial infections in view of its critical role in promoting multidrug resistance. Herein, novel chromanone and 2H-benzo[h]chromene derivatives were designed by means of integrated molecular design and structure-based pharmacophore modeling in an attempt to identify improved efflux pump inhibitors that target Escherichia coli AcrB. The compounds were tested for their efflux inhibitory activity, ability to inhibit efflux, and the effect on bacterial outer and inner membranes. Twenty-three novel structures were identified that synergized with antibacterials tested, inhibited Nile Red efflux, and acted specifically on the AcrB. Among them, WK2, WL7 and WL10 exhibiting broad-spectrum and high-efficiency efflux inhibitory activity were identified as potential ideal AcrB inhibitors. Molecular modeling further revealed that the strong π-π stacking interactions and hydrogen bond networks were the major contributors to tight binding of AcrB.

Synthesis of 3,5-Disubstituted isoxazoles containing privileged substructures with a diverse display of polar surface area

We designed and synthesized the molecular framework of 3,5-disubstituted isoxazoles containing privileged substructures with various substituents which uniquely display polar surface area in a diverse manner. A library of 3,5-disubstituted isoxazoles were systematically prepared via 1,3-dipolar cycloaddition of alkynes with nitrile oxides prepared by two complementary synthetic routes; method A utilized a halogenating agent with a base and method B utilized a hypervalent iodine reagent. Through the biological evaluation of corresponding isoxazoles via three independent phenotypic assays, the different pattern of biological activities was shown according to the type of privileged substructure and substituent. These results demonstrated the significance of molecular design via introducing privileged substructures and various substituents to make a diverse arrangement of polar surface area within a similar 3-dimensional molecular framework.

Modified Coumarins. 36. Synthesis of Linear and Angular Dihydropyranocoumarincarboxylic Acids

The syntheses of linear and angular dihydropyranocoumarincarboxylic acids, modified structural derivatives of dihydroxanthyletin and dihydroseselin, were described.

2,2-dimethyl-chromanone compound and its analogue medical use

The invention belongs to the technical field of medicines and relates to a pharmaceutical use of a 2, 2-dimethyl chromanone type compound and analogs thereof. The structural general formula is as follows, wherein X can be selected from CH2 or C=O; and R and R' are as described in the description. The new compound provided by the invention can be used as an effective anti-platelet medicament, can be particularly applied to the preparation of medicaments for preventing or treating coronary syndrome, myocardial infarction, myocardial ischemia and cardiovascular and cerebrovascular diseases caused by platelet aggregation and can further treat thrombus formation, ischemia, stroke, restenosis or inflammation.

Neuroprotective effects of benzyloxy substituted small molecule monoamine oxidase B inhibitors in Parkinson's disease

The benzyloxy substituted small molecules are well-known highly potent monoamine oxidase B inhibitors, but their therapeutic potential against Parkinson's disease have not been investigated in detail. In this paper, a series of representative benzyloxy substituted derivatives were synthesized and evaluated for MAO-A/B inhibition. In addition, their neuroprotective effects were investigated in 6-OHDA- and rotenone-treated PC12 cells. It was observed that most of the compounds exhibited a marked increase in survival of PC12 cells which treated with the neurotoxins. Among them, 13 exhibited remarkable and balanced neuroprotective potency. The protective effects of 13 against neurotoxins-induced apoptosis were confirmed with flow cytometry and staining methods. Furthermore, 13 also showed good BBB permeability and low toxicity according to in vitro BBB prediction and in vivo acute toxicity test. The results indicated that 13 is an effective and promising candidate to be further developed as disease-modifying drug for Parkinson's disease therapy.

The structure containing piperazine 2,2-dimethyl-chromanone compound and its analogue medical use

The invention belongs to the technical field of medicines and relates to a medical application of 2, 2-dimethyl thiochromanone compounds containing piperazine structures and analogues thereof. The structural general formula of the 2, 2-dimethyl thiochroma