22760-98-1

Usage

Preparation

Preparation by acylation of pyrogallol with propionic acidin the presence of boron trifluoride in ethyl ether for 1 h at 0° (80%) in the presence of Amberlite IR-120 (cation exchange resin sulfonic acid ? type) at 160° for 2–3 h (78%) Zeokarb 225 was found to be as effectivein the presence of zinc chloride, at 130–140° for 90 min (Nencki ? reaction) (35%) in the presence of 70% perchloric acid at reflux for 1 h (33%) Preparation by reaction of propionyl chloride with pyrogallol and heating 4 h on a water bath (75%) Preparation by acylation of pyrogallol with propionic anhydridein the presence of Amberlite IR-120 (cation exchange resin sulfonic acid type) ? at 160° for 2–3 h (79%) Zeokarb 225 was found to be as effectivein the presence of concentrated sulfuric acid (small drops) at 130° for some ? min (65%) in the presence of zinc chloride, but using a mixture of propionic acid/propionic ? anhydride (85/100) at 135–140° for 40 min, then at r.t. overnight (59%).

Upstream product

• 79-03-8 propionyl chloride 
• 87-66-1 2-hydroxyresorcinol 
• 802294-64-0 propionic acid 

Downstream Products

• 124300-24-9 bis(2,3,4-trihydroxypropionylphenyl)methane 
• 124300-25-0 3,4-diethoxymethoxy-2-hydroxy-α-hydroxymethylpropiophenone 
• 46034-82-6 2.3.4-Trihydroxy-1-propyl-benzol 
• 91344-90-0 7,8-Dihydroxy-2,3-dimethyl-chromon 
• 65893-97-2 7,8-dihydroxy-3-methyl-2-phenyl-chromen-4-one 
• 124300-26-1 3,4-diethoxymethoxy-2-hydroxy-propiophenone 

Relevant academic research and scientific papers

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.

An efficient chemo-enzymatic approach towards variably functionalized benzotropolones

An efficient three-step synthesis for benzotropolones via three catalytic steps is presented. Pyrogallol phenones are formed in the first step starting from pyrogallol, which is acylated by proton-catalysis. Catalytic hydrogenation of the phenones yields the corresponding alkylated pyrogallyl dervatives. In the final enzyme-catalyzed step the pyrogallol derivatives are annulated to form the benzotropolone cores. An alternative pathway via the Pechmann reaction is also presented. The combination of the three catalytic steps gives access to a wide range of benzotropolone congeners.