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Synthesis of 4-(3-oxo-3-phenylpropyl)morpholin-4-ium chloride analogues and their inhibitory activities of nitric oxide production in lipopolysaccharide-induced BV2 cells
- Source :
- Bioorganicmedicinal chemistry letters. 36
- Publication Year :
- 2020
-
Abstract
- Based on our previous report that 3-morpholino-1-phenylpropan-1-one 2, one of the fluoxetine’s simplified morpholino analogue, inhibited nitric oxide (NO) production, in this paper, various substituted benzene analogues with morpholine hydrochloride of 2 were synthesized and their inhibitory effects on NO production in lipopolysaccharide (LPS)-induced BV2 cells were tested. Among the synthesized compounds, 2-trifluoromethyl analogue 16n (IC50 = 8.6 μM) showed a significantly higher inhibitory activity than that of the parent compound 2a (IC50 > 50 μM) and suppressed NO production dose-dependently without cytotoxicity. Compound 16n also inhibited iNOS expression in LPS-induced BV2 cells at 2, 10 and 20 μM concentrations. These results suggest that compound 16n inhibited NO production by suppressing the expression of iNOS and can be used as a lead structure for developing new inhibitor of NO production.
- Subjects :
- Lipopolysaccharides
Morpholino
Lipopolysaccharide
Stereochemistry
Morpholines
Clinical Biochemistry
Pharmaceutical Science
Inhibitory postsynaptic potential
Nitric Oxide
01 natural sciences
Biochemistry
Chloride
Nitric oxide
Cell Line
chemistry.chemical_compound
Mice
Structure-Activity Relationship
Chlorides
Drug Discovery
medicine
Animals
No production
Benzene
Cytotoxicity
Molecular Biology
Dose-Response Relationship, Drug
Molecular Structure
010405 organic chemistry
Organic Chemistry
0104 chemical sciences
010404 medicinal & biomolecular chemistry
chemistry
Molecular Medicine
medicine.drug
Subjects
Details
- ISSN :
- 14643405
- Volume :
- 36
- Database :
- OpenAIRE
- Journal :
- Bioorganicmedicinal chemistry letters
- Accession number :
- edsair.doi.dedup.....8df07985bd35dddfaf0b0488f8d6c389