2689-39-6

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-FLUORO-4-NITRO-PHENYL)-MORPHOLINE is used as a reactant for the synthesis of 5-substituted oxazolidinone derivatives. These derivatives exhibit high antimicrobial activity, making them potentially useful in the development of new antibiotics and antifungal agents. The compound's unique structure allows for the creation of novel molecules with improved efficacy and reduced side effects, addressing the growing need for new antimicrobial treatments.

InChI:InChI=1/C10H11FN2O3/c11-9-7-8(13(14)15)1-2-10(9)12-3-5-16-6-4-12/h1-2,7H,3-6H2

Upstream product

• 110-91-8 morpholine 
• 369-34-6 3,4-difluoronitrobenzene 
• 185331-69-5 1-bromo-2-fluoro-4-nitrobenzene 
• 367-11-3 ortho-difluorobenzene 
• 100-00-5 4-chlorobenzonitrile 
• 350-31-2 1-chloro-2-fluoro-4-nitrobenzene 

Downstream Products

• 1101862-63-8 C₁₇H₁₇FN₂O₅S 
• 224323-50-6 linezolid 
• 224323-51-7 3-fluoro-4-(morpholin-4-yl)-phenyl isocyanate 
• 1330034-71-3 (S)-(E,Z)-5-((benzylideneamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one 
• 1345879-82-4 (S)-(E,Z)-5-((4-chlorobenzylideneamino)methyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one 
• 1345879-91-5 (S)-5-(azidomethyl)-3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxazolin-2-one 
• 912359-80-9 (S)-[3-[3-fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]aminomethane 

Relevant academic research and scientific papers

One-pot synthesis and biological evaluation of novel 4-[3-fluoro-4-(morpholin-4-yl)]phenyl-1H-1,2,3-triazole derivatives as potent antibacterial and anticancer agents

In search of better antibacterial and anticancer agents, a series of novel 4-[3-fluoro-4-(morpholin-4-yl)]phenyl-1H-1,2,3-triazole derivatives were synthesized (6a-l and 8a-j) by using 3-fluoro-4-morpholinoaniline, alkyne, and triflyl azide via an in situ

Discovery and optimization of withangulatin A derivatives as novel glutaminase 1 inhibitors for the treatment of triple-negative breast cancer

To develop novel GLS1 inhibitors as effective therapeutic agents for triple-negative breast cancer (TNBC), 25 derivatives were synthesized from the natural inhibitor withangulatin A (IC50 = 18.2 μM). Bioassay optimization identified a novel and

Novel Linezolid analogues with antiparasitic activity against Hymenolepis nana

The stereoselective synthesis and anti- Hymenolepis nana activity of six Linezolid-type compounds, obtained by chemical modification of L-Alanine, are reported in this work. The synthetic strategy was to prepare diasteromeric N,N-dibenzylamino oxazolidino

Catalytic Static Mixers for the Continuous Flow Hydrogenation of a Key Intermediate of Linezolid (Zyvox)

Catalytic static mixers (CSMs) were used for the efficient preparation of a key intermediate of the antimicrobial drug linezolid (Zyvox). The approach combines 3D printing and additive manufacturing techniques with continuous flow processing to produce a

Biofilm inhibition of linezolid-like Schiff bases: Synthesis, biological activity, molecular docking and in silico ADME prediction

Herein, we report the synthesis and screening of linezolid-like Schiff bases as inhibitors of biofilm formation. The result of biofilm inhibition of Pseudomonas aeruginosa suggested that compounds 5h (IC50 value = 12.97 ± 0.33 μM) and 5i (IC50 value = 15.63 ± 0.20 μM) had more inhibitory activity when compared with standard linezolid (IC50 = 15.93 ± 0.18 μM) without affecting the growth of cells (and thus behave as anti-quorum sensing agents). The compounds 5h (MIC range = 2.5-10 μg/mL) and 5i (MIC range = 3.5-10 μg/mL) with 2-chloroquinolinyl and 2-chloro-8-methylquinolinyl motif, respectively, showed antibacterial activity in comparable range of linezolid (MIC range = 2-3 μg/mL) and were more potent when compared with ciprofloxacin (MIC range = 25-50 μg/mL). Thus, the active derivatives were not only potent inhibitors of P. aeruginosa biofilm growth but also efficient antibacterial agents. The docking study of most active compounds 5h and 5i against PqsD enzyme of P. aeruginosa exhibited good binding properties. In silico ADME properties of synthesized compounds were also analyzed and showed potential to develop as good oral drug candidates.

Novel 3-fluoro-4-morpholinoaniline derivatives: Synthesis and assessment of anti-cancer activity in breast cancer cells

Heterocyclic morpholine compounds are well-known for their anti-cancer activity. In this study, novel morpholine and its sulfonamide derivatives were designed and synthesized as potential anti-tumor agents. The new compounds were obtained from amine derivatives via nucleophilic addition reactions, providing the desired products in 70 to 90% yield. The docking analysis was performed for all thirty-one compounds. Out of them, we represent the docking poses for compounds NAM-5 and NAM-7 as representatives. After docking analysis, compounds NAM-5 and NAM- 7 were tested for in vitro antitumor activity against breast cancer cell lines (MCF-7 and MDA-MB-231) and healthy mouse embryonic fibroblast cell line (3T3L-1). Amongst these, sulfonamide group-containing compound NAM-5 showed significant anti-proliferative activity with IC50 of 1.811 μM and 2.143 μM for MCF-7 and MDA-MB-231 cells, respectively. On the other hand, NAM-7 showed good anti-proliferative activity against MCF-7 (IC50 1.883 μM) but slightly lower activity against MDA-MB-231 cells (IC50 4.688 μM). The activity of both the compound was also tested on 3T3L-1 Cell line which showed activity similar to clinically approved anti-cancer drug doxorubicin (DOX). The cell death analysis by flow-cytometry confirmed apoptosis mediated cell death in 3T3L-1, MCF-7 and MDA-MB-231 cells when treated with the NAM-5 and NAM-7, respectively. The results demonstrated that the synthesized sulfonamide derivatives have significant potential as anti-cancer agents and have a substantial importance in cancer therapeutics with favourable safety profile. Structural analysis of docked poses of sulfonamide derivatives attempts to shed light on the structural basis of sulfonamide derivatives based anti-cancer effect.

Benzofuroxan Derivatives as Potent Agents against Multidrug-Resistant Mycobacterium tuberculosis

Tuberculosis (TB) is currently the leading cause of death related to infectious diseases worldwide, as reported by the World Health Organization. Moreover, the increasing number of multidrug-resistant tuberculosis (MDR-TB) cases has alarmed health agencies, warranting extensive efforts to discover novel drugs that are effective and also safe. In this study, 23 new compounds were synthesized and evaluated in vitro against the drug-resistant strains of M. tuberculosis. The compound 6-((3-fluoro-4-thiomorpholinophenyl)carbamoyl)benzo[c][1,2,5]oxadiazole 1-N-oxide (5 b) was particularly remarkable in this regard as it demonstrated MIC90 values below 0.28 μM against all the MDR strains evaluated, thus suggesting that this compound might have a different mechanism of action. Benzofuroxans are an attractive new class of anti-TB agents, exemplified by compound 5 b, with excellent potency against the replicating and drug-resistant strains of M. tuberculosis.

Synthesis of covalent bonding MWCNT-oligoethylene linezolid conjugates and their antibacterial activity against bacterial strains

Nowadays, infectious diseases caused by drug-resistant bacteria have become especially important. Linezolid is an antibacterial drug active against clinically important Gram positive strains; however, resistance showed by these bacteria has been reported. Nanotechnology has improved a broad area of science, such as medicine, developing new drug delivery and transport systems. In this work, several covalently bounded conjugated nanomaterials were synthesized from multiwalled carbon nanotubes (MWCNTs), a different length oligoethylene chain (Sn), and two linezolid precursors (4and7), and they were evaluated in antibacterial assays. Interestingly, due to the intrinsic antibacterial activity of the amino-oligoethylene linezolid analogues, these conjugated nanomaterials showed significant antibacterial activity against various tested bacterial strains in a radial diffusion assay and microdilution method, including Gram negative strains asEscherichia coli(11 mm, 6.25 μg mL?1) andSalmonella typhi(14 mm, ≤0.78 μg mL?1), which are not inhibited by linezolid. The results show a significant effect of the oligoethylene chain length over the antibacterial activity. Molecular docking of amino-oligoethylene linezolid analogs shows a more favorable interaction of theS2-7analog in the PTC ofE. coli.

Synthesis, anti-inflammatory activity and in silico studies of some novel morpholine based carboxamides

Two series of carboxamides were synthesized from 3-fluoro-4-morpholinoaniline and different substituted aromatic/heterocyclic carboxylic acids. All the compounds were characterized by IR, 1H NMR, 13C NMR and mass spectral data. The n

New linezolid synthesis method

The invention belongs to the field of organic synthesis, and particularly relates to a new linezolid synthesis method, which comprises: synthesizing 3-fluoro-4-morpholinophenyl isocyanate by using 3,4-difluoronitrobenzene as a starting raw material, carrying out cyclization on the 3-fluoro-4-morpholinophenyl isocyanate and (R)-epichlorohydrin under the catalysis of MgI2 or MgBr2 in the absence ofa solvent to obtain (R)-3-fluoro-4-morpholinophenyl oxazolidone, and carrying out azide group substitution, reduction and acetylation to obtain linezolid. According to the present invention, by usingthe new linezolid synthesis method, the reaction rate can be significantly accelerated, the yield can be increased, the cost can be reduced, the environment can be protected, the operation is simple,the post-treatment is convenient, and the method is suitable for industrial production.