42059-48-3

Usage

Preparation

Preparation by reaction of acetic anhydride on resaceto-phenone, ? at reflux ? with sodium acetate; ? with pyridine (95%).

Synthesis Reference(s)

Synthetic Communications, 24, p. 1151, 1994 DOI: 10.1080/00397919408011711

InChI:InChI=1/C10H10O4/c1-6(11)9-4-3-8(5-10(9)13)14-7(2)12/h3-5,13H,1-2H3

Upstream product

• 108-05-4 vinyl acetate 
• 89-84-9 2',4'-dihydroxy-4-acetophenone 
• 64-19-7 acetic acid 
• 108-46-3 recorcinol 
• 75-36-5 acetyl chloride 
• 72712-19-7 2,4-diacetoxy acetophenone 
• 108-24-7 acetic anhydride 
• 90-33-5 7-hydroxy-4-methyl-chromen-2-one 
• 127-09-3 sodium acetate 

Downstream Products

• 56133-02-9 2-acetyl-5-(benzyloxy)phenyl acetate 
• 60965-25-5 5'-bromo-2',4'-dihydroxyacetophenone 
• 2896-60-8 4-ethyl-1,3-benzenediol 
• 99186-47-7 4-ethyl resorcinol monoacetate 
• 127265-10-5 4-ethylresorcinol acetate 
• 52751-42-5 2'-acetoxy-4'-hydroxyacetophenone 
• 1201816-77-4 1-cyclohexyl-5-(2-hydroxy-4-methoxybenzoyl)pyridin-2(1H)-one 
• 1201816-79-6 1-butyl-5-(2-hydroxy-4-methoxybenzoyl)pyridin-2(1H)-one 
• 1388221-20-2 1-butyl-5-(2,4-dihydroxybenzoyl)pyridin-2(1H)-one 
• 42059-55-2 7-hydroxy-3-formylchromone 

Relevant academic research and scientific papers

Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway

Eleven 4′-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 μM. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the α,β-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.

Method for preparing 2', 4'-resacetophenone-2'-carboxylic ester

The invention relates to the field of small organic molecule synthesis and particularly provides a synthetic process of 2', 4'-resacetophenone-2'-carboxylic ester. The synthetic process comprises the following steps that 1, 2', 4'-resacetophenone serves as a substrate, acyl chloride serves as acylation reagent, and 2', 4'-resacetophenone-4'-carboxylic ester is synthesized; 2, an acid binding agent with the same equivalent is added to the 2', 4'-resacetophenone-2'-carboxylic ester synthesized in step 1, and a reaction is conducted in polar non-protonic solvent at the room temperature; 3, silica gel column chromatography separation and purification are conducted, target components are collected, and the 2', 4'-resacetophenone-2'-carboxylic ester is obtained. By means of the acyl transfer reaction, the 2', 4'-resacetophenone-2'-carboxylic ester which is difficult to construct through common chemical methods can be synthesized, the reaction is high in atom economy, easy and convenient to operate and ideal in yield, and potential industrial application value is achieved.

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.

Inhibition of Alzheimer's BACE-1 by 2,6-dialkyl-4-chromon-3-yl-1,4-dihydropyridine-3,5-dicarboxylates

Alzheimer's disease is the most common cause of dementia in the elderly, and no disease-modifying therapy is yet available for this devastating pathology. Deposition of different physicochemical forms of amyloid-β peptides is a critical phase in the patho

Synthesis and evaluation of c-Src kinase inhibitory activity of pyridin-2(1H)-one derivatives

Src kinase, a prototype member of the Src family of kinases (SFKs), is over-expressed in various human tumors, and has become a target for anticancer drug design. In this perspective, a series of eighteen 2-pyridone derivatives were synthesized and evaluated for their c-Src kinase inhibitory activity. Among them, eight compounds exhibited c-Src kinase inhibitory activity with IC 50 value of less than 25 μM. Compound 1-[2-(dimethylamino)ethyl]- 5-(2-hydroxy-4-methoxybenzoyl)pyridin-2(1H)-one (36) exhibited the highest c-Src kinase inhibition with an IC50 value of 12.5 μM. Furthermore, the kinase inhibitory activity of compound 36 was studied against EGFR, MAPK and PDK, however no significant activity was observed at the highest tested concentration (300 μM). These results provide insights for further optimization of this scaffold for designing the next generation of 2-pyridone derivatives as candidate Src kinase inhibitors.

BF3·OEt2 mediated regioselective deacetylation of polyacetoxyacetophenones and its application in the synthesis of natural products

We have developed an efficient method to regioselectively deacetylate polyacetoxyacetophenones using BF3·OEt2 in excellent yields and demonstrated the application of the procedure in the synthesis of natural products.

PROCESS FOR THE PREPARATION OF 4-ALKYL RESORCINOL ESTERS

A process for the preparation of one or more esters of 4-alkyl resorcinol comprising the steps of: (i) reacting resorcinol or a pre-cursor thereof with an esterifying agent which comprises at least one of an organic acid, anhydride or chloride having a maximum carbon chain length of 18, at a temperature of 10 to 250 °C; and (ii) reducing the products from step (i) at a pH of 6.5 to 7.5 in the presence of a catalyst in an alcoholic medium.

Ac2O-Py/basic alumina as a versatile reagent for acetylations in solvent-free conditions under microwave irradiation

Acetic anhydride-pyridine over basic alumina has been used in order to carry out acetylations of hydroxy, thiol and amino groups in solvent-free conditions under microwave irradiation. The technique can be extended for selective acetylations by regulation of irradiation time.

Cleavage or acetyl-de-alkylation of 4-methoxybenzyl (mpm) ethers using acetic acid

Aryl (4-methoxyphenyl)methyl (MPM) ethers are cleaved by heating with acetic acid for a few hours at 90°C, producing the corresponding phenols and (4-methoxyphenyl)methyl acetate. Under the same conditions alkyl MPM ethers are transformed directly into the corresponding alkyl acetates.