1565-90-8

Basic information

• Product Name: 4-Fluoro-3-(2-furyl)acrylophenone
• Synonyms: 1-(4-Fluorophenyl)-3-(2-furanyl)-2-propen-1-one
• CAS NO: 1565-90-8
• Molecular Formula: C₁₃H₉FO₂
• Molecular Weight: 216.2078
• Mol File: 1565-90-8.mol
• Article Data: 26

Chemical Properties

• Boiling Point: 333.7°Cat760mmHg
• Flash Point: 155.6°C
• Appearance: /
• Density: 1.169g/cm³
• Vapor Pressure: 0.000174mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 4-Fluoro-3-(2-furyl)acrylophenone(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Fluoro-3-(2-furyl)acrylophenone(1565-90-8)
• EPA Substance Registry System: 4-Fluoro-3-(2-furyl)acrylophenone(1565-90-8)

Safety Data

• Hazardous Substances Data: 1565-90-8(Hazardous Substances Data)

Usage

InChI:InChI=1/C13H9FO2/c14-11-5-3-10(4-6-11)13(15)8-7-12-2-1-9-16-12/h1-9H

Upstream product

• 98-01-1 furfural 
• 403-42-9 1-(4-fluorophenyl)ethanone 
• 61011-54-9 1-(4-Fluoro-phenyl)-2-(triphenyl-λ⁵-arsanylidene)-ethanone 
• 403-29-2 2-bromo-4'-fluoroacetophenone 
• 79101-34-1 acetyl-p-fluorophenyltriphenylarsonium bromide 

Downstream Products

• 1159506-06-5 4-(4-fluorophenyl)-6-(furan-2-yl)pyrimidin-2-amine 
• 1446752-05-1 C₂₄H₁₈FN₃O₃ 

Relevant articles and documents

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.

2,4,6-trisubstituted pyridine compound and application thereof in pesticide

The invention relates to a 2,4,6-trisubstituted pyridine compound and application thereof in pesticides, and belongs to the technical field of pesticides. The structural formula of the 2,4,6-trisubstituted pyridine compound is as shown in formula (I), in

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.