28081-18-7

Basic information

• Product Name: 3-NITRO-4'-FLUOROCHALCONE
• Synonyms: 3-NITRO-4'-FLUOROCHALCONE;1-(4-fluorophenyl)-3-(3-nitrophenyl)-2-propen-1-one;3-Nitro-4'-fluorochalcone 98%;3-Nitro-4'-fluorochalcone98%;3-Nitro-4'-fluorochalcone1-(4-Fluorophenyl)-3-(3-nitrophenyl)-2-propen-1-one;(2E)-1-(4-fluorophenyl)-3-(3-nitrophenyl)prop-2-en-1-one
• CAS NO: 28081-18-7
• Molecular Formula: C₁₅H₁₀FNO₃
• Molecular Weight: 271.24
• Mol File: 28081-18-7.mol

Chemical Properties

• Melting Point: 166-167 °C
• Boiling Point: 429.4°Cat760mmHg
• Flash Point: 213.5°C
• Appearance: /
• Density: 1.3333 (estimate)
• Vapor Pressure: 1.41E-07mmHg at 25°C
• Refractive Index: 1.634
• CAS DataBase Reference: 3-NITRO-4'-FLUOROCHALCONE(CAS DataBase Reference)
• NIST Chemistry Reference: 3-NITRO-4'-FLUOROCHALCONE(28081-18-7)
• EPA Substance Registry System: 3-NITRO-4'-FLUOROCHALCONE(28081-18-7)

Safety Data

• Hazard Codes: Xi
• Statements: 38
• Safety Statements: 37
• Hazardous Substances Data: 28081-18-7(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystalline powder

InChI:InChI=1/C15H10FNO3/c16-13-7-5-12(6-8-13)15(18)9-4-11-2-1-3-14(10-11)17(19)20/h1-10H/b9-4+

Upstream product

• 403-42-9 1-(4-fluorophenyl)ethanone 
• 99-61-6 3-nitro-benzaldehyde 

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.

Design, synthesis, and bioactivities screening of a diaryl ketone-inspired pesticide molecular library as derived from natural products

Three natural products, 1,5-diphenylpentan-1-one, 1,5-diphenylpent-2-en-1-one, and 3-hydroxy-1,5-diphenylpentan-1-one, with good insecticidal activities were extracted from Stellera chamaejasme L. Based on their shared diaryl ketone moiety as 'pharmacophores', a series of diaryl ketones were synthesized and tested for insecticidal activity, acetylcholinesterase inhibitory activity, and antifungal activity. All synthesized compounds showed poor insecticidal and acetylcholinesterase inhibitory activities. Compound III with a furyl ring showed strong activities against plant pathogenic fungi. The IC50 of compound (E)-1-(2,4-dichlorophenyl)-3-(furan-2-yl)- -prop-2-en-1-one (III2) was 1.20mg/L against Rhizoctonia solani, suggesting its strong potential as a novel antifungal drug.