273384-72-8

Basic information

• Product Name: N-(4-Aminophenyl)-2-fluorobenzamide
• Synonyms: N-(4-Aminophenyl)-2-fluorobenzamide;AKOS BBV-006456;OTAVA-BB 1166823
• CAS NO: 273384-72-8
• Molecular Formula: C₁₃H₁₁FN₂O
• Molecular Weight: 230.241
• Mol File: 273384-72-8.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 317.9±27.0 °C(Predicted)
• Appearance: /
• Density: 1.317±0.06 g/cm3(Predicted)
• PKA: 12.27±0.70(Predicted)
• CAS DataBase Reference: N-(4-Aminophenyl)-2-fluorobenzamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(4-Aminophenyl)-2-fluorobenzamide(273384-72-8)
• EPA Substance Registry System: N-(4-Aminophenyl)-2-fluorobenzamide(273384-72-8)

Safety Data

• Hazard Codes: Xi
• HazardClass: IRRITANT
• Hazardous Substances Data: 273384-72-8(Hazardous Substances Data)

Upstream product

• 100-01-6 4-nitro-aniline 
• 445-29-4 o-fluoro-benzoic acid 
• 71026-66-9 N-(tert-butoxycarbonyl)-1,4-phenylenediamine 
• 106-50-3 1,4-phenylenediamine 
• 393-52-2 2-Fluorobenzoyl chloride 
• 350-97-0 2-fluoro-N-(4-nitrophenyl)benzamide 

Relevant articles and documents

Discovery of novel VEGFR-2 inhibitors embedding 6,7-dimethoxyquinazoline and diarylamide fragments

VEGF/VEGFR-2 signaling plays a critical part in tumor angiogenesis. Inhibition of this pathway has been considered as a promising approach for cancer treatment. In this work, a series of 6,7-dimethoxy-4-anilinoquinazoline derivatives bearing diarylamide moiety were designed, synthesized and evaluated as potent inhibitors of VEGFR-2 kinase. Their in vitro antiproliferation activities against two human cancer cell lines Hep-G2 and MCF-7 have also been determined. Among them, compound 14b exhibited the most potent inhibitory activity against VEGFR-2 with IC50 value of 0.016 ± 0.002 μM and it showed the most potent antiproliferative effect against Hep-G2 and MCF-7 with IC50 values at low-micromolar range. Molecular docking studies revealed that these compounds represented by the most potent compound 14b could bind well to the ATP-binding site of VEGFR-2, which suggested that compound 14b could be a potential anticancer agent targeting VEGFR-2.

Design, synthesis and molecular modeling study of certain VEGFR-2 inhibitors based on thienopyrimidne scaffold as cancer targeting agents

Different series of novel thieno [2,3-d]pyrimidine derivative (9a-d,10a-f,l,m and 15a-m) were designed, synthesized and evaluated for their ability to in vitro inhibit VEGFR-2 enzyme. Also, the cytotoxicity of the final compounds was tested against a panel of 60 different human cancer cell lines by NCI. The VEGFR-2 enzyme inhibitory results revealed that compounds 10d, 15d and 15 g are among the most active inhibitors with IC50 values of 2.5, 5.48 and 2.27 μM respectively, while compound 10a remarkably showed the highest cell growth inhibition with mean growth inhibition (GI) percent of 31.57%. It exhibited broad spectrum anti-proliferative activity against several NCI cell lines specifically on human breast cancer (T7-47D) and renal cancer (A498) cell lines of 85.5% and 77.65% inhibition respectively. To investigate the mechanistic aspects underlying the activity, further biological studies like flow cytometry cell cycle together with caspase-3 colorimetric assays were carried on compound 10a. Flow cytometric analysis on both MCV-7 and PC-3 cancer cells revealed that it induced cell-cycle arrest in the G0-G1phase and reinforced apoptosis via activation of caspase-3. Furthermore, molecular modeling studies have been carried out to gain further understanding of the binding mode in the active site of VEGFR-2 enzyme and predict pharmacokinetic properties of all the synthesized inhibitors.

NAPHTHYRIDININONES AS AURORA KINASE INHIBITORS

Naphthyridinone derivative compounds that inhibit Aurora kinase enzymes are disclosed along with pharmaceutical compositions comprising these compounds and methods for synthesizing the same. Such compounds have utility in the treatment of proliferative di