7559-81-1

Usage

Uses

Used in Pharmaceutical Industry:
(2-CHLOROMETHYL)-5-HYDROXY-4H-PYRAN-4-ONE is used as an intermediate in the synthesis of Allo Maltol (A546700), which is a compound with potential pharmaceutical applications. Its role in the synthesis process is crucial for the development of new drugs and therapeutic agents.
Used in Cosmetic Industry:
(2-CHLOROMETHYL)-5-HYDROXY-4H-PYRAN-4-ONE is used as a precursor for the synthesis of esters of 5-hydroxy-2-methyl-4H-pyran-4-one. These esters have been identified as novel tyrosinase inhibitors, which are valuable for their skin-lightening properties. As a result, they are incorporated into cosmetic compositions for their potential to reduce the appearance of pigmentation and promote an even skin tone.

InChI:InChI=1/C6H5ClO3/c7-2-4-1-5(8)6(9)3-10-4/h1,3,9H,2H2

Upstream product

• 501-30-4 5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one 
• 7719-09-7 thionyl chloride 

Downstream Products

• 101605-40-7 5-hydroxy-2-phenothiazin-10-ylmethyl-pyran-4-one 
• 115049-92-8 2-(ethylcarbamimidoylmercapto-methyl)-5-hydroxy-pyran-4-one; hydrochloride 
• 106380-78-3 2-chloromethyl-5-hydroxy-3-(α-hydroxy-benzyl)-pyran-4-one 
• 96583-19-6 5-benzoyloxy-2-chloromethyl-pyran-4-one 
• 103049-23-6 2,5-dibenzoyl-3-benzoyloxy-6-chloromethyl-pyran-4-one 
• 108989-45-3 5-hydroxy-2-(methylcarbamimidoylmercapto-methyl)-pyran-4-one; hydrochloride 
• 100954-98-1 2-chloromethyl-5-trans-cinnamoyloxy-pyran-4-one 
• 100623-20-9 2-chloromethyl-5-phenoxyacetoxy-pyran-4-one 
• 108874-43-7 5-hydroxy-2-(phenylcarbamimidoylmercapto-methyl)-pyran-4-one; hydrochloride 
• 63861-24-5 5-hydroxy-2-(chloromethyl)-4H-pyran-4-onyl triphenyl phosphorane 
• 120902-14-9 5-hydroxy-2-(chloromethyl)-4H-pyran-4-onyl triphenyl phosphorane 
• 1257258-31-3 2-((4-methoxyphenylthio)methyl)-5-hydroxy-4H-pyran-4-one 
• 1178776-89-0 2-((4-hydroxyphenylthio)methyl)-5-hydroxy-4H-pyran-4-one 
• 138426-83-2 5-hydroxy-2-((phenylthio)methyl)-4H-pyran-4-one 

Relevant academic research and scientific papers

Synthesis, solution studies and DFT investigation of a tripodal ligand with 3-hydroxypyran-4-one scaffold

Hydroxypyranones form very stable complexes and possess varied uses in medical applications. They are promising chelators for treating iron overload diseases as they form stable complexes with Fe3+. A novel tripodal ligand tris[(5-hydroxy-4-oxo

ALA hybrid 3-hydroxypyridone derivative as well as preparation method and application thereof

The invention designs and synthesizes a novel anti-tumor active compound with iron chelating property and photosensitive activity based on the principles of reasonable drug design, drug-likeness and the like. The invention aims to provide a preparation me

Bis-maltol-polyamine family: structural modifications at strategic positions. Synthesis, coordination and antineoplastic activity of two new ligands

Two new maltol-based ligands are presented,L1(N,N′-bis((3-hydroxy-6-methyl-4-pyron-2-yl)methyl)-N,N′-dimethylethylenediamine) andL2(N,N′-bis((3-hydroxy-6-hydroxymethyl-4-pyron-2-yl)methyl)-N,N′-dimethylethylenediamine). They were strategically designed by inserting a methyl or hydroxymethyl function at C6, to study the previously hypothesized involvement of that ring position in the anticancer properties and the peculiar metal coordination ability in aqueous solution already shown by this family of ligands. Solid state and solution studies revealed differences neither in the molecular conformation or crystal packing nor in the acid-base behavior compared with the precursor Malten. The introduced substituent groups seem to affect instead both the degradation time (ca.4-5 h forL1andL2vs.10 h for Malten) and the binding properties towards Cu(ii), Zn(ii) and Co(ii), log?Kvalues being the highest forL1within the series of the diamino-bis-maltol ligands. The introduction of -CH2OH at C6 is sufficient to impair the biological activity of the compound and is coherent with the hypothesized mechanism of action.

A new “Mitsunobu homocoupling” reaction using aldol adducts of kojic acid

In this study, we attempted to carry out the Mitsunobu 1,4-elimination using the kojic acid analog 3, which carries a hydroxymethyl group on C-6 introduced by aldol condensation, to obtain an effective Michael acceptor 4. To the ethyl acetate solution of

Quinazolinone-dihydropyrano[3,2-b]pyran hybrids as new α-glucosidase inhibitors: Design, synthesis, enzymatic inhibition, docking study and prediction of pharmacokinetic

A series of new quinazolinone-dihydropyrano[3,2-b]pyran derivatives 10A-L were synthesized by simple chemical reactions and were investigated for inhibitory activities against α-glucosidase and α-amylase. New synthesized compounds showed high α-glucosidase inhibition effects in comparison to the standard drug acarbose and were inactive against α-amylase. Among them, the most potent compound was compound 10L (IC50 value = 40.1 ± 0.6 μM) with inhibitory activity around 18.75-fold more than acarboase (IC50 value = 750.0 ± 12.5 μM). This compound was a competitive inhibitor into α-glucosidase. Our obtained experimental results were confirmed by docking studies. Furthermore, the cytotoxicity of the most potent compounds 10L, 10G, and 10N against normal fibroblast cells and in silico druglikeness, ADME, and toxicity prediction of these compounds were also evaluated.

Compound targeting ubiquitination degradation tyrosinase as well as preparation method and application thereof

A Tyr inhibitor kojic acid is covalently bound to a pomalidomide or VHL enzyme targeting ligand through a linkage chain to obtain a specific structure, and the preparation method is simple to operate and mild in condition. The generation of melanin is inhibited, the anti-melanin tumor effect is remarkable, and the safety period of vegetables and fruits can be remarkably prolonged. The compound targeted ubiquitination degradation tyrosinase provided by the invention has wide application prospects in medicine, food and cosmetics.

Pyrone compound as well as preparation method and application thereof

The invention provides a pyrone compound and a preparation method and application thereof. The molecular formula of the pyrone compound is C18H18N6O3S. The preparation method of the pyrone compound comprises the three steps of Schiff base synthesis, kojic

Synthesis and Some Properties of New 5-Hydroxy-2-[(hetarylthio)methyl]-4H-pyran-4-ones

Abstract: The reaction of 2-thioxoazines with chlorokojic acid in the presence of KOH in DMF led to the formation of new hybrid molecules containing fragments of kojic acid and azaheterocycle linked by the SCH2 spacer. In silico prediction of b

Development of dual inhibitors targeting pyruvate dehydrogenase kinases and human lactate dehydrogenase A: High-throughput virtual screening, synthesis and biological validation

Most cancer cells feature an altered glucose metabolism from oxidative phosphorylation to cytoplasmic glycolysis. Pyruvate dehydrogenase kinases (PDKs) and lactate dehydrogenase A (LDHA) play crucial roles in promotion of glycolysis, thus the inhibition of both enzymes is considered a promising strategy for developing of anticancer therapeutics. Herein, we describe the first discovery of series novel dual inhibitors targeting PDKs and LDHA. We identified 6 hits from a library database containing 485465 compounds through a high-throughput virtual screening assay. Hit-to-lead optimization enabled us to discover two compounds, namely 20e and 20k, which inhibited PDKs with IC50 values of 0.8, and 1.6 μM, respectively, and inhibited LDHA with IC50 values of 0.15 and 0.7 μM, respectively. Meanwhile, the two compounds reduced A549 cell proliferation with EC50 values of 13.2, and 15.7 μM. Furthermore, 20e and 20k decreased the lactate formation, and increased oxygen consumption, suggesting the two compounds modulated the glucose metabolic pathways in cancer cells.

Adamantyl pyran-4-one derivatives and their in vitro antiproliferative activity

Abstract: Pyran-4-one (maltol, kojic acid and chlorokojic acid 1) esters of adamantan-1-ylacetic acid were prepared through efficient synthetic routes in good yields and evaluated for their in vitro antiproliferative activity on four cancer cell lines: K562 (chronic myelogenous leukemia), HeLa (cervical cancer), Caco-2 (colorectal adenocarcinoma) and NCI-H358 (bronchioalveolar carcinoma). The results indicate that the presence and the position of the adamantyl acyl group or chlorine atom are the necessary requirement for antitumor activity of pyranone systems. Derivatives of kojic acid with either free (compounds 1 and 8) or acylated 5-OH group (compounds 2 and 9) have shown good-to-moderate activity (IC50 values ranging from 13.1 to 43.0?μM) on all cell lines. Adamantyl kojic acid derivative 5 with a free OH group on the position 2 showed activity only on the K562 cell line. It seems that removal of halogen or adamantyl unit from position 2 elicits antileukemic activity, as observed in compound 5. The positive influence of the adamantyl unit was also observed on a 3-OH acylated derivative of maltol I which was also selectively active on the same cell line. 5-O-benzylated adamantyl compounds 6 and 7 and unmodified starting pyranones were found to be inactive. Antibacterial activity of compounds was also evaluated on S. aureus ATCC 13709, M. catarrhalis ATCC 23246, E. faecalis ATCC29212 and E. coli TolC-Tn10, but no activity was observed (MIC values 128–256?μg/mL). Graphical abstract: [Figure not available: see fulltext.]