5166-94-9

Upstream product

• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 89-98-5 2-chloro-benzaldehyde 

Downstream Products

• 120421-92-3 3-[2,3-Dibromo-3-(2-chloro-phenyl)-propionyl]-4-hydroxy-6-methyl-pyran-2-one 
• 1278443-06-3 5-(4-hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7-(2-chlorophenyl)-2,3,6,7-tetrahydro-1,4-thiazepine 
• 120421-96-7 2-(2-chlorophenyl)-7-methylpyrano<4,3-b>pyran-4(H), 5(H)-dione 

Relevant academic research and scientific papers

5-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-7-phenyl-2,3,6,7-tetrahydro-1, 4-thiazepines as compounds with high affinity at the benzodiazepine binding site on GABAA receptors

A series of thiazepines has been studied as new ligands for the benzodiazepine binding site of the GABAA receptor. Compounds with high affinity and weak selectivity regarding α1β 2γ2, α2β3γ 2, α3β3γ2, and α5β3γ2 subtypes were found. The pharmacophore is discussed based on experimental and theoretical results. The thiazepine sulfur atom was found to be able to act as hydrogen bond acceptor.

Regioselective three component domino synthesis of polyhydrospiro[indoline-3,3'-pyrrolizine]-2-one via [3+2] Cycloaddition reaction

In present work, we have reported the synthesis and characterisation of novel hexahydrospiro[indoline-3,3′-pyrrolizine]-2-one derivatives in good to excellent yields via [3+2] cycloaddtion reaction in regioselective manner. These compounds were synthesized via multicomponent reaction of substituted 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-one, isatin, L-proline at room temperature. All the synthesized hexahydrospiro molecules were characterized by 1H and 13C NMR, IR spectra, mass spectra and elemental analysis. Regioselectivity in synthesized molecules were also explained on the basis of secondary orbital interactions. A simple and facile methodology is developed which has great importance in synthetic chemistry.

Synthesis of new dihydropyrazoles of designed curcumin analogues

Present work demonstrates a facile synthesis of a series of 20 dihydropyrazole derivatives from well designed curcumin analogues by reaction of chalcone derivatives with phenylhydrazine. All the synthesized compounds were characterized by spectroscopic (1H and 13C NMR, IR spectra), spectrometric (Mass spectra) data and elemental analysis. Synthesized dihydropyrazoles have diversity points on attached phenyl ring. Effect of substituent on reactivity was explained on the basis of electronic effect generated due to groups on phenyl ring. Presence of dd (double doublet) in 1H NMR spectrum of dihydropyrazoles was also explained due to presence of optically active carbon of pyrazole ring.

Synthesis and in vitro evaluation of substituted 3-cinnamoyl-4-hydroxy-pyran-2-one (CHP) in pursuit of new potential antituberculosis agents

Tuberculosis is an ever-evolving infectious disease that urgently needs new drugs. In the search for new antituberculosis agents, a library of 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones (CHPs) (2a-2y) was synthesized and evaluated against a standard virulent laboratory strain of Mycobacterium tuberculosis H37Rv. Out of 25 compounds, 11, 5, 7 and 2 (2a and 2u) showed least, moderate, good and appreciable activities, respectively, based on minimum inhibitory concentrations (MICs). Both 2a and 2u exhibited an MIC value of 4 μg ml-1, which was close to those of standard antituberculosis drugs ethambutol, streptomycin and levofloxacin. Neither 2a nor 2u showed any activity against Gram-positive or Gram-negative bacteria and even against non-tuberculous mycobacterium, i.e. Mycobacterium smegmatis. Thus, like the antituberculosis drugs rifampicin, isoniazid and pretomanid, they are highly TB specific. All the pyrone-based chalcones showed no recognizable level of cytotoxicity against normal human kidney cell line (HEK-293) up to 80 μM concentration and 11 exhibited an IC50 ≤ 100 μM (highest tested concentration). On further investigation, both 2a and 2u proved to be nontoxic against four human cell lines but 2a proved to be a better choice as it did not reach IC50 even at 100 μM (highest tested concentration) while the IC50 of 2u was around 80 μM. In conclusion, our results demonstrate that 2a is specific against M. tuberculosis with no appreciable toxicity; its activity matches that of some clinically approved antituberculosis drugs and it therefore merits further evaluation.

Reaction of heteroaryl hydrazines with 3-Cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones: Synthesis of some novel pyrazolines and their iodine(III) mediated conversion to corresponding pyrazoles

A series of some novel 5-aryl-3-(4-hydroxy-6-methyl-2H-pyran-2-oxo-3-yl)-1-heteroaryl pyrazolines have been prepared by the reaction of 3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-ones i.e., chalcone analogues of dehydroacetic acid (DHA) with various heteroaryl hydrazines and converted to corresponding pyrazoles with iodobenzene diacetate in good yields.