1609033-76-2

Basic information

• Product Name: methyl 2-((4-(4-(4-fluorophenoxy)phenylsulfonamido)-1-methoxynaphthalen-2-yl)thio)acetate
• Synonyms: methyl 2-((4-(4-(4-fluorophenoxy)phenylsulfonamido)-1-methoxynaphthalen-2-yl)thio)acetate
• CAS NO: 1609033-76-2
• Molecular Weight: 527.594
• Mol File: 1609033-76-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: methyl 2-((4-(4-(4-fluorophenoxy)phenylsulfonamido)-1-methoxynaphthalen-2-yl)thio)acetate(CAS DataBase Reference)
• NIST Chemistry Reference: methyl 2-((4-(4-(4-fluorophenoxy)phenylsulfonamido)-1-methoxynaphthalen-2-yl)thio)acetate(1609033-76-2)
• EPA Substance Registry System: methyl 2-((4-(4-(4-fluorophenoxy)phenylsulfonamido)-1-methoxynaphthalen-2-yl)thio)acetate(1609033-76-2)

Safety Data

• Hazardous Substances Data: 1609033-76-2(Hazardous Substances Data)

Upstream product

• 1429765-71-8 methyl 2-((1-methoxy-4-nitronaphthalen-2-yl)thio)acetate 
• 4900-63-4 1-methoxy-4-nitronaphthalene 
• 1429765-70-7 2-iodo-1-methoxy-4-nitronaphthalene 
• 1429765-78-5 methyl 2-((4-amino-1-methoxynaphthalen-2-yl)thio)acetate 
• 192329-91-2 4-(4-fluorophenoxy)benzenesulfonyl chloride 

Downstream Products

• 1429764-73-7 2-((4-(4-(4-fluorophenoxy)phenylsulfonamido)-1-hydroxynaphthalen-2-yl)thio)acetic acid 

Relevant articles and documents

3-substituted-N-(4-hydroxynaphthalen-1-yl)arylsulfonamides as a novel class of selective Mcl-1 inhibitors: Structure-based design, synthesis, SAR, and biological evaluation

Mcl-1, an antiapoptotic member of the Bcl-2 family of proteins, is a validated and attractive target for cancer therapy. Overexpression of Mcl-1 in many cancers results in disease progression and resistance to current chemotherapeutics. Utilizing high-throughput screening, compound 1 was identified as a selective Mcl-1 inhibitor and its binding to the BH3 binding groove of Mcl-1 was confirmed by several different, but complementary, biochemical and biophysical assays. Guided by structure-based drug design and supported by NMR experiments, comprehensive SAR studies were undertaken and a potent and selective inhibitor, compound 21, was designed which binds to Mcl-1 with a Ki of 180 nM. Biological characterization of 21 showed that it disrupts the interaction of endogenous Mcl-1 and biotinylated Noxa-BH3 peptide, causes cell death through a Bak/Bax-dependent mechanism, and selectively sensitizes Eμ-myc lymphomas overexpressing Mcl-1, but not Eμ-myc lymphoma cells overexpressing Bcl-2. Treatment of human leukemic cell lines with compound 21 resulted in cell death through activation of caspase-3 and induction of apoptosis.