404-71-7

Usage

Uses

Used in Pharmaceutical Industry:
3-Fluorophenyl isocyanate is used as a key intermediate in the synthesis of linezolid, an antibiotic medication used to treat a variety of bacterial infections. Its presence in the compound contributes to its antimicrobial properties.
Used in Organic Chemistry:
3-Fluorophenyl isocyanate is used as a reagent in the preparation of substituted 6-ureidopurines, such as 6(N2-3-fluorophenyl)ureidopurine. These compounds are of interest in medicinal chemistry and drug development due to their potential biological activities and therapeutic applications.

InChI:InChI=1/C7H4FNO/c8-6-2-1-3-7(4-6)9-5-10/h1-4H

Upstream product

• 75-44-5 phosgene 
• 372-19-0 meta-fluoroaniline 
• 503-38-8 trichloromethyl chloroformate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 625-98-9 3-chlorofluorobenzene 
• 917-61-3 sodium isocyanate 

Downstream Products

• 330-39-2 3-(3-fluorophenyl)-1,1-dimethylurea 
• 330-41-6 1,1-diethyl-3-(3-fluorophenyl)urea 
• 330-43-8 N'-(3-fluoro-phenyl)-N,N-bis-(2-hydroxy-ethyl)-urea 
• 22546-46-9 C₈H₁₀FN₃O 
• 64393-03-9 N-(3-fluorophenyl)-N'-cyclopropyl-urea 
• 23122-47-6 C₁₅H₁₃FN₂O₄ 
• 102422-27-5 Imidazole-1-carboxylic acid (3-fluoro-phenyl)-amide 
• 79513-90-9 1-(2,6-Dimethyl-pyrimidin-4-yl)-3-(3-fluoro-phenyl)-urea 
• 90513-62-5 1-(3-Fluoro-phenylcarbamoyl)-pyrrolidine-2,5-dicarboxylic acid diethyl ester 
• 125766-99-6 1-(5-Benzo[1,3]dioxol-5-yl-[1,3,4]oxadiazol-2-yl)-3-(3-fluoro-phenyl)-urea 
• 125766-98-5 1-(3-Fluoro-phenyl)-3-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]oxadiazol-2-yl]-urea 
• 125766-65-6 1-(3-Fluoro-phenyl)-3-[5-(3,4,5-trimethoxy-phenyl)-[1,3,4]thiadiazol-2-yl]-urea 
• 125766-66-7 1-(5-Benzo[1,3]dioxol-5-yl-[1,3,4]thiadiazol-2-yl)-3-(3-fluoro-phenyl)-urea 
• 35366-75-7 1-(2,6-Dichloro-benzoyl)-3-(3-fluoro-phenyl)-urea 

Relevant academic research and scientific papers

Synthesis and biological evaluation of novel 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives as potential antitumor agents

A novel series of 4-(4-formamidophenylamino)-N-methylpicolinamide derivatives were synthesized and evaluated against different tumor cell lines. Experiments in vitro showed that these derivatives could inhibit the proliferation of two kinds of human cancer cell lines (HepG2, HCT116) at low micromolar concentrations and the most potent analog 5q possessed broad-spectrum antiproliferative activity. Experiments in vivo demonstrated that 5q could effectively prolong the longevity of colon carcinoma-burdened mice and slow down the progression of cancer cells by suppression of angiogenesis and the induction of apoptosis and necrosis.

Synthesis and structure-activity relationship study of pyrrolidine-oxadiazoles as anthelmintics against Haemonchus contortus

Parasitic roundworms (nematodes) are significant pathogens of humans and animals and cause substantive socioeconomic losses due to the diseases that they cause. The control of nematodes in livestock animals relies heavily on the use of anthelmintic drugs. However, their extensive use has led to a widespread problem of drug resistance in these worms. Thus, the discovery and development of novel chemical entities for the treatment of parasitic worms of humans and animals is needed. Herein, we describe our medicinal chemistry optimization efforts of a phenotypic hit against Haemonchus contortus based on a pyrrolidine-oxadiazole scaffold. This led to the identification of compounds with potent inhibitory activities (IC50 = 0.78–22.4 μM) on the motility and development of parasitic stages of H. contortus, and which were found to be highly selective in a mammalian cell counter-screen. These compounds could be used as suitable chemical tools for drug target identification or as lead compounds for further optimization.

Discovery of SP-96, the first non-ATP-competitive Aurora Kinase B inhibitor, for reduced myelosuppression

Aurora Kinase B is a serine-threonine kinase known to be overexpressed in several cancers, with no inhibitors approved for clinical use. Herein, we present the discovery and optimization of a series of novel quinazoline-based Aurora Kinase B inhibitors. The lead inhibitor SP-96 shows sub-nanomolar potency in Aurora B enzymatic assays (IC50 = 0.316 ± 0.031 nM). We identified the important pharmacophore features resulting in selectivity against receptor tyrosine kinases. Particularly, SP-96 shows >2000 fold selectivity against FLT3 and KIT which is important for normal hematopoiesis. This could diminish the adverse effect of neutropenia reported in the clinical trials of the Aurora B inhibitor Barasertib, which inhibits FLT3 and KIT in addition to Aurora B. Enzyme kinetics of SP-96 shows non-ATP-competitive inhibition which makes it a first-in-class inhibitor. Further, SP-96 shows selective growth inhibition in NCI60 screening, including inhibition of MDA-MD-468, a Triple Negative Breast Cancer cell line.

2,3,4,9-tetrahydro-1H-pyridino-[3,4-b]-indole compound and application thereof

The invention belongs to the technical field of medicine, and relates to a 2,3,4,9-tetrahydro-1H-pyridino-[3,4-b]-indole compound and application thereof, in particular to a series of methyl 1-aryl-2-(aryl-formamyl)-2,3,4,9-tetrahydro-1H-pyridino-[3,4-b]-indole-3-carboxylate compounds, and an optical activator or racemate thereof or a pharmaceutically-acceptable salt, hydrate or solvate thereof. The invention further relates to application of the compound to the preparation of medicaments for treating and/or preventing cancers and other hyperplastic diseases. The structures of the compound andthe optical activator or racemate thereof or the pharmaceutically-acceptable salt, hydrate or solvent thereof are shown as a general formula I, wherein Ar1 and Ar2 are described in the claims and description. The general formula I is shown in the description.

Design, synthesis and structure-activity relationship of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure as multi-target inhibitors against receptor tyrosine kinase

Inspired by that the multi-target inhibitors against receptor tyrosine kinases (RTKs) have significantly improved the effect of clinical treatment for cancer, and based on the chemical structure of Linifanib (ABT-869, Abbott), two series of diaryl-ureas with novel isoxazol[3,4-b]pyridine-3-amino-structure were designed and synthesized as multi-target inhibitors against RTKs. The preliminary biological evaluation showed that several compounds exhibited comparable potency with Linifanib. Compound S21 was identified as the most potent inhibitor against Fms-like tyrosine kinase 3 (FLT-3), kinase insert domain containing receptor (KDR) and platelet-derived growth factor receptor β (PDGFR-β) with its IC50 values were 4 nM, 3 nM and 8 nM respectively, it also showed potent inhibitory activities against several cancer cells.

Design and Synthesis of 4-Alkylidene-β-lactams: Benzyl- and Phenethyl-carbamates as Key Fragments to Switch on Antibacterial Activity

The emergence of multidrug-resistant bacterial strains is particularly important in chronic pathologies such as cystic fibrosis (CF), in which persistent colonization and selection of resistant strains is favored by the frequent and repeated use of antibacterial agents. Staphylococcus aureus is a common pathogen in CF patients that has an associated increased multidrug resistance. In previous studies we demonstrated that the presence of a 4-alkylidene side chain directly linked to a β-lactam appeared to strengthen the potency against S. aureus, especially against methicillin-resistant S. aureus (MRSA) strains. In the present study, 21 new 4-alkylidene-β-lactams were synthesized and evaluated for antibacterial activity. We designed the new compounds to have aryl, benzyl, or phenethyl-carbamate groups on the C3 hydroxyethyl side chain. We found a correlation between biological activity and the nitrogen substituent of the carbamate group, and two phenethyl-carbamate β-lactams were shown to be valuable antibacterial agents against selected linezolid-resistant strains, with a minimum inhibitory concentrations of 2–4 mg L?1.

Discovery of novel anti-angiogenesis agents. Part 8: Diaryl thiourea bearing 1H-indazole-3-amine as multi-target RTKs inhibitors

VEGFR-2, TIE-2, and EphB4 are essential for both angiogenesis and tumorigenesis. Herein, we designed and prepared three classes of multi-target inhibitors based on the extensive sequence homology along the kinase domain of angiogenic RTKs. Biological evaluation indicated that these multi-target inhibitors exhibited considerable potential as novel anti-angiogeneic and anticancer agents. Among them, a diaryl thiourea bearing 1H-indazole-3-amine (16a) displayed the most potent RTK inhibition and excellent selectivity. It also showed inhibition on viability of human umbilical vein endothelial cells and anti-proliferation against a broad spectrum of cancer cells. Therefore, 1H-indazole-3-amine could serve as a promising hinge binding group for multi-target inhibitors of VEGFR-2, Tie-2, and EphB4.

Discovery of novel anti-angiogenesis agents. Part 7: Multitarget inhibitors of VEGFR-2, TIE-2 and EphB4

Herein, we embarked on a structural optimization campaign aiming at the discovery of second generation anti-angiogenesis agents with our previously reported BPS-7 as lead compound. A library of 27 compounds has been afforded based on the highly conserved ATP-binding pocket of VEGFR-2, Tie-2, and EphB4. Several title compounds exhibited simultaneous inhibitory effects against three angiogenic RTKs. These compounds with a ‘triplet’ inhibition profile have been identified as novel anti-angiogenic and anticancer agents. The representative VDAU11 displayed prominent anti-angiogenic and anticancer potency and could be considered as a candidate for further optimization. These results indicate that N-(pyridin-2-yl)acrylamide could serve as a novel hinge-binding group of triple inhibitors.

Design, synthesis and structure-activity relationships of novel diaryl urea derivatives as potential EGFR inhibitors

Two novel series of diaryl urea derivatives 5a-i and 13a-l were synthesized and evaluated for their cytotoxicity against H-460, HT-29, A549, and MDA-MB-231 cancer cell lines in vitro. Therein, 4-aminoquinazolinyl-diaryl urea derivatives 5a-i demonstrated significant activity, and seven of them are more active than sorafenib, with IC50 values ranging from 0.089 to 5.46 μM. Especially, compound 5a exhibited the most active potency both in cellular (IC50 = 0.15, 0.089, 0.36, and 0.75 μM, respectively) and enzymatic assay (IC50 = 56 nM against EGFR), representing a promising lead for further optimization.

Having plant growth-regulating active compound and method for preparing same

The invention discloses a compound with plant-growth regulating activity. The compound has a structure in a genera formula (I), wherein in the general formula (I), R and R1 are various substituent groups on a benzene ring; R represents a hydrogen atom, alkyl, a fluorine atom, a helium atom, nitryl and trifluoromethyl; R1 represents the hydrogen atom and the fluorine atom, or R and R1 are -CH=CH-CH=CH- and is respectively connected with the second and third bits or the third and fourth bits of the benzene ring. The compound is prepared from ferrocene ethyl ketoxime reacting with substituted benzene isocyanide acid ester. The invention also provides application of the compound as an effective component of a plant growth regulator.