717-21-5

Usage

Uses

Used in Pharmaceutical Industry:
3-(2-furyl)acrylophenone is used as a building block for the development of new pharmaceuticals due to its unique chemical structure and potential biological activities, including anti-inflammatory, anticancer, and antimicrobial properties. Its versatility in synthesis allows for the creation of a wide range of therapeutic agents.
Used in Agrochemical Industry:
In the agrochemical sector, 3-(2-furyl)acrylophenone is utilized as a key intermediate in the synthesis of various agrochemicals. Its reactivity and properties make it suitable for the development of compounds with pesticidal or herbicidal activities, contributing to crop protection and yield enhancement.
Used in Organic Synthesis:
3-(2-furyl)acrylophenone is employed as a versatile intermediate in organic synthesis for the preparation of a variety of organic compounds. Its unique structure allows for multiple synthetic pathways, making it a valuable component in the creation of specialty chemicals and complex organic molecules.
Used in Research and Development:
3-(2-furyl)acrylophenone is used as a subject of research for exploring its potential biological activities and applications in various fields of chemistry and pharmaceutical science. Its unique properties and reactivity make it an interesting candidate for the development of new compounds and understanding of chemical reactions and mechanisms.

InChI:InChI=1/C13H10O2/c1-2-12(14)10-5-3-6-11(9-10)13-7-4-8-15-13/h2-9H,1H2

Upstream product

• 98-01-1 furfural 
• 13735-81-4 1-styrenyloxytrimethylsilane 
• 199443-91-9 3-(furan-2-yl)-1-phenyl-3-(phenylsulfonyl)propan-1-one 
• 87831-11-6 3-(2-furyl)-3-hydroxy-1-phenyl-propan-1-one 
• 536-74-3 phenylacetylene 
• 98-00-0 (2-furyl)methyl alcohol 
• 98-85-1 1-Phenylethanol 
• 111393-11-4 3-(furan-2-yl)-1-phenylprop-2-en-1-ol 
• 13735-78-9 1-phenyl-2-(trimethylsilyl)ethanone 
• 80671-28-9 furan-2-yl(trimethylsilyl)methanone 
• 70-11-1 α-bromoacetophenone 
• 98-86-2 acetophenone 

Downstream Products

• 1794-08-7 (3R)-3-(furan-2-yl)-1,3-diphenylpropan-1-one 
• 3878-19-1 fuberidazole 
• 3208-40-0 2-(3-phenylprop-1-yl)-tetrahydrofuran 
• 92036-18-5 1-phenyl-3-tetrahydro[2]furyl-propan-1-ol 
• 61833-72-5 (4-furan-2-yl-4,5-dihydro-1H-pyrazol-3-yl)-phenyl-methanone 
• 64388-79-0 2-furan-2-yl-4-phenyl-1-pyridin-3-yl-butane-1,4-dione 
• 110442-38-1 5-furan-2-yl-3-phenyl-4,5-dihydro-pyrazole-1-carbothioic acid anilide 
• 1124383-32-9 3-(allylthio)-3-(furan-2-yl)-1-phenylpropan-1-one 
• 1124383-40-9 diethyl 2-allyl-2-[1-(furan-2-yl)-3-oxo-3-phenylpropyl]malonate 
• 1124383-43-2 diethyl 2-(but-3-enyl)-2-[1-(furan-2-yl)-3-oxo-3-phenylpropyl]malonate 
• 1204687-32-0 C₂₅H₂₀N₄O 
• 1233334-62-7 4-(furan-2-yl)-7,7-dimethyl-2-phenyl-4,6,7,8-tetrahydroquinolin-5(1H)-one 
• 1256449-83-8 thioacetic acid S-[1-(furan-2-yl)-3-oxo-3-phenylpropyl]ester 

Relevant academic research and scientific papers

Cascade Reaction of α, β-Unsaturated Ketones and 2-Aminoaryl Alcohols for the Synthesis of 3-Acylquinolines by a Copper Nanocatalyst

3-Acylquinolines possess widespread applications in functional chemicals. However, the convenient and selective synthesis of such important substructures has to date remained a challenge. Herein, we report a method to access 3-acylquinolines from α, β-unsaturated ketones and 2-aminoaryl alcohols in one pot with a copper nanocatalyst supported on nitrogen-silica-doped carbon (Cu/N?SiO2?C). Mechanistically, the construction of the product involves a cascade procedure including radical-type oxidation of 2-aminoaryl alcohols, aza-Michael addition and annulation. This developed protocol proceeds with merits of mild reaction conditions, good functional group tolerance, earth-abundant and reusable copper catalyst, easily available stocks and O2 as the sole oxidant, which provides an alternative way for the sustainable synthesis of quinoline derivatives. (Figure presented.).

Pharmacophore hybridization approach to discover novel pyrazoline-based hydantoin analogs with anti-tumor efficacy

In search for new and safer anti-cancer agents, a structurally guided pharmacophore hybridization strategy of two privileged scaffolds, namely diaryl pyrazolines and imidazolidine-2,4-dione (hydantoin), was adopted resulting in a newfangled series of compounds (H1-H22). Herein, a bio-isosteric replacement of “pyrrolidine-2,5-dione” moiety of our recently reported antitumor hybrid incorporating diaryl pyrazoline and pyrrolidine-2,5-dione scaffolds with “imidazoline-2,4-dione” moiety has been incorporated. Complete biological studies revealed the most potent analog among all i.e. compound H13, which was at-least 10-fold more potent compared to the corresponding pyrrolidine-2,5-dione, in colon and breast cancer cells. In-vitro studies showed activation of caspases, arrest of G0/G1 phase of cell cycle, decrease in the expression of anti-apoptotic protein (Bcl-2) and increased DNA damage. In-vivo assay on HT-29 (human colorectal adenocarcinoma) animal xenograft model unveiled the significant anti-tumor efficacy along with oral bioavailability with maximum TGI 36% (i.p.) and 44% (per os) at 50 mg/kg dose. These findings confirm the suitability of hybridized pyrazoline and imidazolidine-2,4-dione analog H13 for its anti-cancer potential and starting-point for the development of more efficacious analogs.

TBHP/Cu(OAc)2 mediated oxidation of pyrazolines: A convenient method for the preparation of pyrazoles

An efficient and simple oxidative protocol has been developed for the preparation of pyrazoles from pyrazolines mediated by TBHP/Cu(OAc)2 at room temperature. The present protocol has been successfully applied for the preparation of various pyrazole compounds from heterocyclic pyrazolines.

Rapid umpolung Michael addition of isatin N, N ′-cyclic azomethine imine 1,3-dipoles with chalcones

The umpolung Michael addition of isatin N,N′-cyclic azomethine imine 1,3-dipoles with chalcones is reported. The reaction could be finished within a very short time (0.3-2 min), with 3,3-disubstituted oxindole derivatives obtained in moderate to excellent yields with promising dr values. Unusual Michael adducts were obtained in moderate to high yields (26-98%) with low to high diastereoselectivities (0.8: 1 to 8.5: 1 dr). All the synthesized compounds (3, 3′, 4, 5, 5′, 7, 7′, 9 and 9′) were well characterized by FTIR, NMR, and mass spectral analyses and further confirmed by the single-crystal X-ray diffraction analysis of compounds 3aa and 4n.

Potassium Base-Catalyzed Michael Additions of Allylic Alcohols to α,β-Unsaturated Amides: Scope and Mechanistic Insights

We report herein the first KHMDS-catalyzed Michael additions of allylic alcohols to α,β-unsaturated amides through allylic isomerization. The reaction proceeds smoothly in the presence of only 5 mol% of KHMDS to afford a variety of 1,5-ketoamides in high yields. Mechanistic investigations, including experimental and computational studies, reveal that the KHMDS-catalyzed in-situ generation of the enolate from the allylic alcohol through a tunneling-assisted 1,2-hydride shift is the key to the success of this transformation. (Figure presented.).

Double-edged Swords: Diaryl pyrazoline thiazolidinediones synchronously targeting cancer epigenetics and angiogenesis

In the present study, two novel series of compounds incorporating naphthyl and pyridyl linker were synthesized and biological assays revealed 5-((6-(2-(5-(2-chlorophenyl)-3-(4-fluorophenyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethoxy) naphthalene-2-yl)methylene)thiazolidine-2,4-dione (14b) as the most potent dual inhibitors of vascular endothelial growth factors receptor-2 (VEGFR-2) and histone deacetylase 4 (HDAC4). Compounds 13b, 14b, 17f, and 21f were found to stabilize HDAC4; where, pyridyl linker swords were endowed with higher stabilization effects than naphthyl linker. Also, 13b and 14b showed best inhibitory activity on VEGFR-2 as compared to others. Compound 14b was most potent as evident by in-vitro and in-vivo biological assessments. It displayed anti-angiogenic potential by inhibiting endothelial cell proliferation, migration, tube formation and also suppressed new capillary formation in the growing chick chorioallantoic membranes (CAMs). It showed selectivity and potency towards HDAC4 as compared to other HDAC isoforms. Compound 14b (25 mg/kg, i.p.) also indicated exceptional antitumor efficacy on in-vivo animal xenograft model of human colorectal adenocarcinoma (HT-29). The mechanism of action of 14b was also confirmed by western blot.

Palladium-Catalyzed Synthesis of α-Methyl Ketones from Allylic Alcohols and Methanol

One-pot synthesis of α-methyl ketones starting from 1,3-diaryl propenols or 1-aryl propenols and methanol as a C1 source is demonstrated. This one-pot isomerization-methylation is catalyzed by commercially available Pd(OAc)2 with H2O as the only by-product. Mechanistic studies and deuterium labelling experiments indicate the involvement of isomerization of allyl alcohol followed by methylation through a hydrogen-borrowing pathway in these isomerization-methylation reactions.

Synthesis and Biological Evaluation of Pyrazoline and Pyrrolidine-2,5-dione Hybrids as Potential Antitumor Agents

In search of novel and effective antitumor agents, pyrazoline-substituted pyrrolidine-2,5-dione hybrids were designed, synthesized and evaluated in silico, in vitro and in vivo for anticancer efficacy. All the compounds exhibited remarkable cytotoxic effects in MCF7 and HT29 cells. The excellent antiproliferative activity toward MCF7 (IC50=0.78±0.01 μM), HT29 (IC50=0.92±0.15 μM) and K562 (IC50=47.25±1.24 μM) cell lines, prompted us to further investigate the antitumor effects of the best compound S2 (1-(2-(3-(4-fluorophenyl)-5-(p-tolyl)-4,5-dihydro-1H-pyrazol-1-yl)-2-oxoethyl)pyrrolidine-2,5-dione). In cell-cycle analysis, S2 was found to disrupt the growth phases with increased cell population in G1/G0 phase and decreased cell population in G2/M phase. The excellent in vitro effects were also supported by inhibition of anti-apoptotic protein Bcl-2. In vivo tumor regression studies of S2 in HT29 xenograft nude mice, exhibited equivalent and promising tumor regression with maximum TGI, 66 % (i. p. route) and 60 % (oral route) at 50 mg kg?1 dose by both the routes, indicating oral bioavailability and antitumor efficacy. These findings advocate that hybridization of pyrazoline and pyrrolidine-2,5-dioes holds promise for the development of more potent and less toxic anticancer agents.

Chiral Hydroxytetraphenylene-Catalyzed Asymmetric Conjugate Addition of Boronic Acids to Enones

(S)-2,15-Br2-DHTP-catalyzed asymmetric conjugate addition of boronic acids to β-trifluoromethyl α,β-unsaturated ketones and enones was studied. The reaction afforded the corresponding Michael addition products in moderate to high yields with excellent enantioselectivities (up to 99:1 er). This catalytic system features mild reaction conditions, high efficiency, and tolerance to heteroarylboronic acids.

Reaction condition controlled nickel(ii)-catalyzed C-C cross-coupling of alcohols

The challenge in the C-C cross-coupling of secondary and primary alcohols using acceptorless dehydrogenation coupling (ADC) is the difficulty in accurately controlling product selectivities. Herein, we report a controlled approach to a diverse range of β-alkylated secondary alcohols, α-alkylated ketones and α,β-unsaturated ketones using the ADC methodology employing a Ni(ii) 4,6-dimethylpyrimidine-2-thiolate cluster catalyst under different reaction conditions. This catalyst could tolerate a wide range of substrates and exhibited a high activity for the annulation reaction of secondary alcohols with 2-aminobenzyl alcohols to yield quinolines. This work is an example of precise chemoselectivity control by careful choice of reaction conditions.