6152-57-4

Usage

Uses

Used in Pharmaceutical Industry:
AIDS-089094, 3-Methoxy-4-phenyl-1H-quinolin-2-one is used as an antiviral agent for the treatment of HIV. It works by inhibiting the replication of the virus, specifically by targeting the TNFα-induced pathway. This makes it a promising candidate for further research and development in the field of HIV treatment.
However, the lack of availability of AIDS-089094, 3-Methoxy-4-phenyl-1H-quinolin-2-one has restricted more intensive investigation and development. Further research is needed to explore its potential applications and optimize its production for widespread use in the pharmaceutical industry.

Biological Activity

5 μm: blocks activation of the hiv long terminal repeat by tnf-α in hela cellso-methylviridicatin, a natural derivative of the alkaloid mycotoxin viridicatin, is produced by several species in the genus, penicillium. it is demonstrated that o-methylviridicatin, as an inhibitor, blocks the tumor necrosis factor alpha (tnfα)-induced replication of human immunodeficiency virus (hiv). tnfα increases the binding of the cellular transcription factor nf-κb to the hiv long terminal repeat (ltr), which directly triggers transcription of the latent provirus.

in vitro

o-methylviridicatin had an inhibitory effect on the tnfα-triggered replication of hiv ltr in hela cells. in addition, o-methylviridicatin dose-dependently dampened virus production in the om-10.1 cell line, which was measured by the output of p24 core antigen into the culture medium. it was demonstrated that the suppressive effect of o-methylviridicatin was not reversed even if the concentration of tnfα was increased 10-fold [1].

IC 50

2.5 μm: inhibits virus production in om-10.1 cells (hl-60 promyelocytes infected with hiv-1) treated with tnf-α.

references

[1]. heguy, a., cai, p., meyn, p., houck, d., russo, s., & michitsch, r. et al. isolation and characterization of the fungal metabolite 3-o-methylviridicatin as an inhibitor of tumour necrosis factor-induced human immunodeficiency virus replication. antiviral chemistry and chemotherapy. 1998; 9(2): 149-155.

InChI:InChI=1/C16H13NO2/c1-19-15-14(11-7-3-2-4-8-11)12-9-5-6-10-13(12)17-16(15)18/h2-10H,1H3,(H,17,18)

Upstream product

• 74-88-4 methyl iodide 
• 14371-10-9 (E)-3-phenylpropenal 
• 1372125-89-7 4-phenyl-1-tosyl-1,4-dihydroquinoline 
• 1372126-03-8 4-phenyl-1-tosyl-1,2,3,4-tetrahydroquinoline-2,3-diol 
• 1372126-05-0 3-hydroxy-4-phenyl-1-tosylquinolin-2(1H)-one 
• 1372126-07-2 3-methoxy-4-phenyl-1-tosylquinolin-2(1H)-one 
• 137845-37-5 4-methyl-N-((1E,2E)-3-phenylallylidene)benzenesulfonamide 
• 2835-77-0 (2-aminophenyl)(phenyl)methanone 

Relevant academic research and scientific papers

Bicyclic alkaloid compound, preparation method and applications thereof

The present invention relates to a bicyclic alkaloid compound, or a tautomer, a stereoisomer, a racemate, the non-equal mixture of enantiomers, a geometric isomer, a solvate, a pharmaceutically acceptable salt or a prodrug thereof, and a pharmaceutical composition containing the compound. The invention further discloses uses of the compounds and the pharmaceutical composition thereof as drugs, especially as anti-inflammatory drugs and anti-fibrotic drugs.

Synthesis of aryl-substituted 1,4-dihydroquinolines by [4+2] cycloaddition of benzyne with 1-azadienes

The synthesis of aryl-substituted 1,4-dihydroquinolines can be achieved using a [4+2] cycloaddition between benzyne and various aryl-substituted 1-azadienes. The conditions are tolerated by N-aryl-, alkyl-, tosyl-, and tert-butoxycarbonyl-protected 1-azad

Synthesis of 3-O-methylviridicatin analogues with improved anti-TNF-α properties

We synthesized 3-O-methylviridicatin 1 and several analogues of this fungal metabolite. We showed that replacement of the methoxy moiety by a thiomethyl enhanced dramatically its ability to inhibit TNF-α secretion. These results strongly suggest that 4-phenyl-3-methylthioquinolinone 3 may provide the basis for the development of new anti-inflammatory agents.