17172-56-4

Basic information

• Product Name: 2-(4-formylphenoxy)-N-(naphthalen-1-yl)acetamide
• Synonyms: 2-(4-formylphenoxy)-N-(naphthalen-1-yl)acetamide
• CAS NO: 17172-56-4
• Molecular Weight: 305.333
• Mol File: 17172-56-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 2-(4-formylphenoxy)-N-(naphthalen-1-yl)acetamide(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-formylphenoxy)-N-(naphthalen-1-yl)acetamide(17172-56-4)
• EPA Substance Registry System: 2-(4-formylphenoxy)-N-(naphthalen-1-yl)acetamide(17172-56-4)

Safety Data

• Hazardous Substances Data: 17172-56-4(Hazardous Substances Data)

Upstream product

• 134-32-7 1-amino-naphthalene 
• 832-89-3 2-chloro-N-(1-naphthyl)acetamide 
• 123-08-0 4-hydroxy-benzaldehyde 

Downstream Products

• 1266715-61-0 (Z)-2-(4-((2,4-dioxothiazolidin-5-ylidene)methyl)phenoxy)-N-(naphthalen-1-yl)acetamide 
• 1310561-85-3 2-(4-((4,6-dioxo-2-thioxotetrahydropyrimidin-5(6H)-ylidene)methyl)phenoxy)-N-(naphthalen-1-yl)acetamide 

Relevant articles and documents

CYP enzymes, expressed within live human suspension cells, are superior to widely-used microsomal enzymes in identifying potent CYP1A1/CYP1B1 inhibitors: Identification of quinazolinones as CYP1A1/CYP1B1 inhibitors that efficiently reverse B[a]P toxicity and cisplatin resistance

Microsomal cytochrome P450 (CYP) enzymes, isolated from recombinant bacterial/insect/yeast cells, are extensively used for drug metabolism studies. However, they may not always portray how a developmental drug would behave in human cells with intact intracellular transport mechanisms. This study emphasizes the usefulness of human HEK293 kidney cells, grown in ‘suspension’ for expression of CYPs, in finding potent CYP1A1/CYP1B1 inhibitors, as possible anticancer agents. With live cell-based assays, quinazolinones 9i/9b were found to be selective CYP1A1/CYP1B1 inhibitors with IC50 values of 30/21 nM, and > 150-fold selectivity over CYP2/3 enzymes, whereas they were far less active using commercially-available CYP1A1/CYP1B1 microsomal enzymes (IC50, >10/1.3–1.7 μM). Compound 9i prevented CYP1A1-mediated benzo[a]pyrene-toxicity in normal fibroblasts whereas 9b completely reversed cisplatin resistance in PC-3/prostate, COR-L23/lung, MIAPaCa-2/pancreatic and LS174T/colon cancer cells, underlining the human-cell-assays’ potential. Our results indicate that the most potent CYP1A1/CYP1B1 inhibitors would not have been identified if one had relied merely on microsomal enzymes.

Synthesis and biological evaluation of novel 5-benzylidenethiazolidine-2,4- dione derivatives for the treatment of inflammatory diseases

Twenty-two compounds based on thiazolidine-2,4-dione moiety were synthesized and evaluated for the inhibitory potency on the production of nitric oxide (NO), inducible nitric oxide synthase (iNOS) activity, and the generation of prostaglandin E2 (PEG2). (Z)-N-(3-Chlorophenyl)-2-(4- ((2,4-dioxothiazolidin-5-ylidene) methyl) phenoxy) acetamide (3I), superior to the commercial anti-inflammatory drug indomethacin, significantly inhibited iNOS activity (IC50 = 8.66 μM), iNOS-mediated NO, and cyclooxygenase (COX)-2-derived PGE2 production (IC50 = 4.16 and 23.55 μM, respectively) on lipopolysaccharide (LPS)-induced RAW 264.7 cells. Docking study revealed that 3I was perfectly docking into the active site of murine iNOS and suppressed the expression of iNOS protein as evidenced by Western blot analysis. At the dose of 50 mg/kg, oral administration of 3I possessed protective properties in both carrageenan-induced paw edema and adjuvant-induced arthritis rat models.