50607-35-7

Upstream product

• 771-03-9 3-acetyl-4-hydroxy-6-methyl-2H-pyran-2-one 
• 113689-79-5 methyl 2-ethyl-3,5-dioxohexanoate 
• 675-10-5 4-hydroxy-6-methyl-2-pyron 
• 143456-22-8 2,2-dimethyl-5-(3-oxobutanoyl)-1,3-dioxane-4,6-dione 
• 29736-80-9 3,5-dioxohexanoic acid methyl ester 

Downstream Products

• 82420-00-6 3,3'-<(4-Chlorphenyl)-methylen>-bis-(4-hydroxy-6-methyl-2H-pyran-2-on) 
• 82420-03-9 3,3’-(4-methoxyphenyl)methylenebis(4-hydroxy-6-methyl-2H-pyran-2-one) 

Relevant academic research and scientific papers

Isolation of the antibiotic pseudopyronine B and SAR evaluation of C3/C6 alkyl analogs

Natural products are an abundant source of structurally diverse compounds with antibacterial activity that can be used to develop new and potent antibiotics. One such class of natural products is the pseudopyronines. Here we present the isolation of pseudopyronine B (2) from a Pseudomonas species found in garden soil in Western North Carolina, and SAR evaluation of C3 and C6 alkyl analogs of the natural product for antibacterial activity against Gram-positive and Gram-negative bacteria. We found a direct relationship between antibacterial activity and C3/C6 alkyl chain length. For inhibition of Gram-positive bacteria, alkyl chain lengths between 6 and 7 carbons were found to be the most active (IC50?=?0.04–3.8?μg/mL) whereas short alkyl chain analogs showed modest activity against Gram-negative bacteria (IC50?=?223–304?μg/mL). This demonstrates the potential for this class of natural products to be optimized for selective activity against either Gram-positive or Gram-negative bacteria.

Design, synthesis, and biological evaluation of novel 2H-pyran-2-one derivatives as potential HIV-1 reverse transcriptase inhibitors

In search for more effective drugs against HIV infection acting as non-nucleoside reverse transcriptase inhibitors (NNRTIs), a series of new molecules with hybrid structures based on the natural product (+)-calanolide A and the synthetic molecule α-APA, known as potent and selective inhibitors of this enzyme, were selected by docking calculations. A convergent synthetic strategy gave 21 compounds with a 2 H-pyran-2-one structural unit and bearing isosteric modifications, which were tested against HIV-infected CEM cell cultures. Only compound 6 (4-((2-(1H-indol-3-yl)ethyl)amino)-6-methyl-2H-pyran-2-one) displayed inhibitory activity (EC50: 25-50 μM). However, it was associated with a relatively high cytostatic effect on human T lymphocyte (CEM) cell cultures, not easily predictable, neither by the chemical structure nor by the computational approach. Although this drug design has failed in selecting a novel scaffold for NNRTIs, the results have driven the interest towards new potential antitumor molecules showing activity against L1210 murine leukemia and HeLa cervix carcinoma cells, among which compound 21 (6-methyl-4-((2-(naphthalen-1-yl)ethyl)sulfonyl)-2H-pyran-2-one) was the most effective (IC50: 0.95 and 2.9 μM, respectively).

A new approach to the synthesis of 3,6- and 5,6-dialkyl derivatives of 4-hydroxy-2-pyrone. Synthesis of rac-germicidin

A new approach to the synthesis of 3,6- and 5,6-dialkyl-4-hydroxy-2- pyrones has been developed. The method includes the formation of acylated Meldrum's acids (5-(2-alkyl-3-oxoacyl)-2,2-dimethyl-1,3-dioxane-4,6-diones) followed by their thermal transformation. Introduction of 3-alkyl substituents was accomplished by acylation of 4-hydroxy-2-pyrones and ionic hydrogenation of the 3-acyl derivatives obtained. The effectiveness of this new approach has been demonstrated in the synthesis of rac-germicidin, an autoregulative germination inhibitor of Streptomyces viridochromogenes NRRL B-1551.

A simple and effective method for the reduction of acyl substituted heterocyclic 1,3-dicarbonyl compounds to alkyl derivatives by zinc - acetic acid - hydrochloric acid

3-Acyl-4-hydroxy-2(1H)-quinolones (1a-k) were reduced in good yields (66-97%) to 3-alkyl-4-hydroxy-2(1H)-quinolinones (2a-k) using zinc powder (particle size 〈45 μm) in acetic acid/hydrochloric acid. This method could be transformed to 3-acetyl-4-hydroxy-

REDUCTION OF α-PYRONE DERIVATIVES WITH BORANE-METHYLSULFIDE COMPLEX

Selective reduction of the 5-carbomethoxy- and the 5-carboethoxy-4-hydroxy-2H-pyran-2-one derivatives (5a-11, 19) to yield the 5-hydroxymethyl derivatives (12-18) was accomplished using 1.1 mol equivalent of borane-methyl sulfide complex.Additionally, red

Copper and cobalt mediated regioselective alkylation of polyketide models: Methyl 3,5-dioxohexanoate and triacetic acid lactone

Regioselective C-alkylations at the intercarbonyl positions C-4 and C-2 of the polyketide model methyl 3,5-dioxohexanoate, 1, have been acomplished through reactions of its cobalt(II), 4a, and copper(II), 4b, complexes respectively. Some examples of double alkylations at both positions are presented. Cyclizations of the regioselectively substituted diketoesters so prepared gave triacetic acid lactone derivatives regioselectively alkylated at C-5 and at C-3.

COPPER COMPLEX PROTECTION IN THE REGIOSELECTIVE ALKYLATION OF METHYL 3,5-DIOXOHEXANOATE. PREPARATION OF 3-ALKYL DERIVATIVES OF 4-HYDROXY-6-METHYL-2-PYRONE

Protection of the diketone moiety of the polyketide model methyl 3,5-dioxohexanoate by copper(II) complex formation followed by alkylation of the free C-2 position results in overall regioselective alkylation of the diketoester to afford methyl 2-alkyl-3,5-dioxohexanoates, which under cyclization afford 3-alkyl derivatives of triacetic acid lactone.

Reduction of Isopropylidene Acylmalonates, 5-Acylbarbituric Acids, and 3-Acyl-4-hydroxycoumarins to the Corresponding Alkyl Derivatives by Sodium Cyanoborohydride-Acetic Acid

Isopropylidene acylmalonates, 5-acylbarbituric acids, and 3-acyl-4-hydroxycoumarins are readily reduced to the corresponding alkyl derivatives by sodium cyanoborohydride-acetic acid.The cyclic substrates are readily prepared by the acylation of isopropylidene malonate, barbituric acid (or its N,N'-dimethyl derivative), and 4-hydroxycoumarin, according to procedures developed by other workers.The reductions take place upon addition of a 2 mol equiv of sodium cyanoborohydride to a mixture of the acyl compound and acetic acid.This reductive transformation completes a synthetic method for the preparation of the alkyl derivatives starting from the parent compound.