394-02-5

Usage

Uses

Used in Pharmaceutical Synthesis:
5-Fluoro-2-nitrobenzoyl chloride is used as a reagent in the pharmaceutical industry for the synthesis of various drugs. It is particularly valuable for the introduction of the 5-fluoro-2-nitrobenzoyl group into drug molecules, which can enhance their pharmacological properties, such as potency, selectivity, and metabolic stability.
Used in Agrochemical Development:
In the agrochemical industry, 5-Fluoro-2-nitrobenzoyl chloride serves as a key intermediate in the synthesis of pesticides and other agrochemicals. Its incorporation into these compounds can improve their effectiveness in controlling pests and diseases, as well as their environmental compatibility.
Used in Material Science:
5-Fluoro-2-nitrobenzoyl chloride is also utilized in the development of new materials and compounds in material science. Its unique chemical structure allows for the creation of novel materials with specific properties, such as improved thermal stability, mechanical strength, or optical characteristics.
Safety Considerations:
Due to its high reactivity and potential hazards, 5-Fluoro-2-nitrobenzoyl chloride should be handled with extreme care in a controlled laboratory environment. Proper safety measures, including the use of personal protective equipment and adherence to established safety protocols, are essential to minimize risks associated with its use.

Upstream product

• 320-98-9 5-fluoro-2-nitrobenzoic acid 
• 455-38-9 3-fluorobenzoic acid 

Downstream Products

• 393-85-1 methyl 5-fluoro-2-nitrobenzoate 
• 445-77-2 5-fluoro-2-nitro-benzoic acid propyl ester 
• 342-47-2 5-fluoro-2-nitro-benzoic acid-(2-dimethylamino-ethyl ester); hydrochloride 
• 364-51-2 ethyl 5-fluoro-2-nitrobenzoate 
• 320-93-4 5-fluoro-2-nitro-benzoic acid-(3-diethylamino-propylester); hydrochloride 
• 390-09-0 5-fluoro-2-nitro-benzoic acid-(2-dipropylamino-ethyl ester); hydrochloride 
• 445-80-7 5-fluoro-2-nitro-benzoic acid-(3-dipropylamino-propylester); hydrochloride 
• 445-79-4 5-fluoro-2-nitro-benzoic acid-(2-dibutylamino-ethyl ester); hydrochloride 
• 445-81-8 5-fluoro-2-nitro-benzoic acid-(3-dibutylamino-propylester); hydrochloride 
• 445-78-3 5-fluoro-2-nitro-benzoic acid butyl ester 
• 149744-26-3 N-(2-Chloro-pyridin-3-yl)-5-fluoro-2-nitro-benzamide 
• 123064-58-4 N-(2-nitro-5-fluorobenzoyl)pyrrolidine-2-carboxaldehyde diethyl thioacetal 
• 851848-03-8 methyl 3-[(5-fluoro-2-nitrobenzoyl)amino]-4-methylbenzoate 
• 909391-53-3 5-fluoro-N-(2-(isopropylamino)-2-oxoethyl)-2-nitrobenzamide 

Relevant academic research and scientific papers

2-((3,5-Dinitrobenzyl)thio)quinazolinones: Potent Antimycobacterial Agents Activated by Deazaflavin (F420)-Dependent Nitroreductase (Ddn)

Swapping the substituents in positions 2 and 4 of the previously synthesized but yet undisclosed 5-cyano-4-(methylthio)-2-arylpyrimidin-6-ones 4, ring closure, and further optimization led to the identification of the potent antitubercular 2-thio-substituted quinazolinone 26. Structure-activity relationship (SAR) studies indicated a crucial role for both meta-nitro substituents for antitubercular activity, while the introduction of polar substituents on the quinazolinone core allowed reduction of bovine serum albumin (BSA) binding (63c, 63d). While most of the tested quinazolinones exhibited no cytotoxicity against MRC-5, the most potent compound 26 was found to be mutagenic via the Ames test. This analogue exhibited moderate inhibitory potency against Mycobacterium tuberculosis thymidylate kinase, the target of the 3-cyanopyridones that lies at the basis of the current analogues, indicating that the whole-cell antimycobacterial activity of the present S-substituted thioquinazolinones is likely due to modulation of alternative or additional targets. Diminished antimycobacterial activity was observed against mutants affected in cofactor F420 biosynthesis (fbiC), cofactor reduction (fgd), or deazaflavin-dependent nitroreductase activity (rv3547), indicating that reductive activation of the 3,5-dinitrobenzyl analogues is key to antimycobacterial activity.

Discovery of 5-(4-methylpiperazin-1-yl)-2-nitroaniline derivatives as a new class of SIRT6 inhibitors

SIRT6 is a deacetylase of histone H3 and inhibitors of SIRT6 have been thought as potential agents for treatment of diabetes. Herein we report the discovery of a series of new SIRT6 inhibitors containing the skeleton 1-phenylpiperazine. Among them, compound 5-(4-methylpiperazin-1-yl)-2-nitroaniline (6d) is the most potent one, which showed an IC50 value of 4.93 μM against SIRT6 in the Fluor de Lys (FDL) assay. It displayed KD values of 9.76 μM and 10 μM in surface plasmon resonance (SPR) and isothermal titration calorimetry (ITC) assays, respectively. In selectivity assay, 6d showed no activity against other members of the HDAC family (SIRT1-3 and HDAC1-11) at concentrations up to 200 μM. In a mouse model of type 2 diabetes, 6d could significantly increase the level of glucose transporter GLUT-1, thereby reducing blood glucose. Overall, this study provides a promising lead compound for subsequent drug discovery targeting SIRT6.

Synthesis, docking, 3-D-qsar, and biological assays of novel indole derivatives targeting serotonin transporter, dopamine D2 receptor, and mao-a enzyme: In the pursuit for potential multitarget directed ligands

A series of 27 compounds of general structure 2,3-dihydro-benzo[1,4]oxazin-4-yl)-2-{4-[3-(1H-3indolyl)-propyl]-1-piperazinyl}-ethanamides, Series I: 7(a-o) and (2-{4-[3-(1H-3-indolyl) -propyl]-1-piperazinyl}-acetylamine)-N-(2-morfolin-4-yl-ethyl)-fluorinated benzamides Series II: 13(a-l) were synthesized and evaluated as novel multitarget ligands towards dopamine D2 receptor, serotonin transporter (SERT), and monoamine oxidase-A (MAO-A) directed to the management of major depressive disorder (MDD). All the assayed compounds showed affinity for SERT in the nanomolar range, with five of them displaying Ki values from 5 to 10 nM. Compounds 7k, Ki = 5.63 ± 0.82 nM, and 13c, Ki = 6.85 ± 0.19 nM, showed the highest potencies. The affinities for D2 ranged from micro to nanomolar, while MAO-A inhibition was more discrete. Nevertheless, compounds 7m and 7n showed affinities for the D2 receptor in the nanomolar range (7n: Ki = 307 ± 6 nM and 7m: Ki = 593 ± 62 nM). Compound 7n was the only derivative displaying comparable affinities for SERT and D2 receptor (D2/SERT ratio = 3.6) and could be considered as a multitarget lead for further optimization. In addition, docking studies aimed to rationalize the molecular interactions and binding modes of the designed compounds in the most relevant protein targets were carried out. Furthermore, in order to obtain information on the structure-activity relationship of the synthesized series, a 3-D-QSAR CoMFA and CoMSIA study was conducted and validated internally and externally (q2 = 0.625, 0.523 for CoMFA and CoMSIA and r2ncv = 0.967, 0.959 for CoMFA and CoMSIA, respectively).

Novel quinazoline derivatives bearing various 6-benzamide moieties as highly selective and potent EGFR inhibitors

A series of novel quinazoline derivatives bearing various C-6 benzamide substituents were synthesized and evaluated as EGFR inhibitors, and most showed significant inhibitory potency against EGFR kinase. In particular, compound 6g possessed potent inhibitory activity against EGFR wild-type (IC50 = 5 nM), and strong antiproliferative activity against HCC827 and Ba/F3 (L858R) cell lines. Kinase profiling against a panel of 365 kinases showed that 6g was highly selective for EGFR. Furthermore, 6g showed desirable properties in assays of liver microsome metabolic stability and cytochromes P450 inhibition and preliminary pharmacokinetic study. The overall attractive profile of 6g made it an interesting compound for further development.

Copper-Catalyzed Domino Reaction Involving Nitro as an Unexpected Leaving Group: Construction of Dibenzo-Fused Azepinone Ring

A copper-catalyzed new domino reaction allowed the facile and direct construction of the dibenzo-fused azepinone ring leading to an array of novel small molecules. The co-catalyst, ligand or additive free one-pot method afforded a unique class of function

SUBSTITUTED AMINOPYRIMIDINE COMPOUNDS AND METHODS OF USE

The invention relates to the preparation and use of new aminopyrimidine derivatives as drug candidates in free form or in pharmaceutically acceptable salt form and formulations thereof for the modulation of a disorder or disease which is mediated by the activity of the PI3K enzymes. The invention also provides pharmaceutically acceptable compositions comprising such compounds and methods of using the compositions in the treatment of disorders or diseases, such as disorders of immunity and inflammation in which PI3K enzymes play a role in leukocyte function, and hyperproliferative disorders associated with PI3K activity, including but not restricted to leukemias and solid tumors, in mammals, especially humans.

TETRAHYDROISOQUINOLIN-2-YL-(QUINAZOLIN-4-YL) METHANONE COMPOUNDS AS CANCER CELL GROWTH INHIBITORS

Tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone derivatives represented by formula (I), pharmacologically acceptable salts thereof, and compositions containing such compounds are described. Methods for treating hyperproliferative disorders by administering the compounds are also described. 1,2,3,4-tetrahydroisoquinoline derivatives for making tetrahydroisoquinolin-2-yl-(quinazolin-4-yl)methanone compounds are also described.

Silver-and gold-mediated domino transformation: A strategy for synthesizing benzo[ e ]indolo[1,2-a ]pyrrolo/pyrido[2,1-c ][1,4]diazepine-3,9-diones

We reported a strategy for the synthesis of fused heterocyclic compounds benzo[e]indolo[1,2-a]pyrrolo/pyrido[2,1-c][1,4]diazepine-3,9-diones via an AgSbF6/gold-complex catalyzed one-pot cascade transformation. The strategy is tolerant of a broad range of substrates and affords a series of intriguing fused diazepinedione heterocycles.(Figure Presented)

CONDENSED AZINE - DERIVATIVES FOR THE TREATMENT OF DISEASES RELATED TO THE ACETYLCHOLINE RECEPTOR

The present invention relates to a heterocyclic derivative of formula (I) wherein the variables are as defined in the specification or to a pharmaceutically acceptable salt or solvate thereof. The present invention further relates to pharmaceutical compositions comprising said heterocyclic derivatives and to their use in therapy, for instance in the treatment or prevention of disorders mediated by nicotinic acetylcholine receptors, such as schizophrenia and Alzheimer's disease.

The synthesized novel fluorinated compound (LJJ-10) induces death receptor- and mitochondria-dependent apoptotic cell death in the human osteogenic sarcoma U-2 OS cells

We designed the 6-fluoro-2-(3-fluorophenyl)-4-substituted anilinoquinazoline derivatives as less toxic anti-cancer candidates. Our result demonstrated that LJJ-10 has greater cytotoxicity than that of the other compounds in human osteogenic sarcoma U-2 OS cells. LJJ-10-induced apoptosis was associated with enhancing ROS generation, DNA damage, and an increase of the protein levels of Fas, FasL, FADD, caspase-8, cytochrome c, Apaf-1, AIF, Endo G, caspase-9 and caspase-3 in U-2 OS cells. LJJ-10-triggered growth inhibition was significantly attenuated by N-acetylcysteine, cyclosporine A, anti-FasL monoclonal antibody, and caspase-8, -9 and -3 specific inhibitors in U-2 OS cells. We suggest that LJJ-10-induced apoptotic cell death in U-2 OS cells through death receptor- and mitochondria-dependent apoptotic signaling pathways.