1314406-38-6

Basic information

• Product Name: Methyl 2-[5-[2-(2,4-Dichlorophenoxy)phenyl]-2H-tetrazol-2-yl]acetate
• Synonyms: Methyl 2-[5-[2-(2,4-Dichlorophenoxy)phenyl]-2H-tetrazol-2-yl]acetate;5-[2-(2,4-dichlorophenoxy)phenyl]-2H-Tetrazole-2-acetic acid methyl ester
• CAS NO: 1314406-38-6
• Molecular Formula: C₁₆H₁₂Cl₂N₄O₃
• Molecular Weight: 379.19748
• Mol File: 1314406-38-6.mol
• Article Data: 1

Chemical Properties

• Boiling Point: 502.2±60.0 °C(Predicted)
• Appearance: /
• Density: 1.47±0.1 g/cm3(Predicted)
• PKA: -0.36±0.12(Predicted)
• CAS DataBase Reference: Methyl 2-[5-[2-(2,4-Dichlorophenoxy)phenyl]-2H-tetrazol-2-yl]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Methyl 2-[5-[2-(2,4-Dichlorophenoxy)phenyl]-2H-tetrazol-2-yl]acetate(1314406-38-6)
• EPA Substance Registry System: Methyl 2-[5-[2-(2,4-Dichlorophenoxy)phenyl]-2H-tetrazol-2-yl]acetate(1314406-38-6)

Safety Data

• Hazardous Substances Data: 1314406-38-6(Hazardous Substances Data)

Upstream product

• 671186-08-6 5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazole 
• 96-32-2 bromoacetic acid methyl ester 
• 175136-80-8 2-(2,4-dichlorophenoxy)benzonitrile 

Downstream Products

• 1479163-36-4 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(3-methoxyphenyl)hydrazinecarbothioamide 
• 1479163-41-1 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(3-nitrophenyl)hydrazinecarbothioamide 
• 1479163-40-0 N-(4-chlorophenyl)-2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)hydrazinecarbothioamide 
• 1479163-37-5 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(4-methoxyphenyl)hydrazinecarbothioamide 
• 1479163-39-7 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(4-nitrophenyl)hydrazinecarbothioamide 
• 1479163-42-2 N-(3,5-bis(trifluoromethyl)phenyl)-2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)hydrazinecarbothioamide 
• 1479163-31-9 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(3,5-dimethylphenyl)hydrazinecarboxamide 
• 1479163-32-0 N-(4-chlorophenyl)-2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)hydrazinecarboxamide 
• 1479163-30-8 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(4-methoxyphenyl)hydrazinecarboxamide 
• 1479163-34-2 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(4-nitrophenyl)hydrazinecarboxamide 
• 1479163-33-1 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(3,5-dichlorophenyl)hydrazinecarboxamide 
• 685120-57-4 2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetohydrazide 
• 1479163-35-3 2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)-N-(m-tolyl)hydrazinecarbothioamide 
• 1479163-38-6 N-(3-chlorophenyl)-2-(2-(5-(2-(2,4-dichlorophenoxy)phenyl)-2H-tetrazol-2-yl)acetyl)hydrazinecarbothioamide 

Relevant articles and documents

Development of 3-phenyl-N-(2-(3-phenylureido)ethyl)-thiophene-2-sulfonamide compounds as inhibitors of antiapoptotic Bcl-2 family proteins

Antiapoptotic Bcl-2 family proteins, such as Bcl-xL, Bcl-2, and Mcl-1, are often overexpressed in tumor cells, which contributes to tumor cell resistance to chemotherapies and radiotherapies. Inhibitors of these proteins thus have potential applications in cancer treatment. We discovered, through structure-based virtual screening, a lead compound with micromolar binding affinity to Mcl-1 (inhibition constant (Ki)=3 μM). It contains a phenyltetrazole and a hydrazinecarbothioamide moiety, and it represents a structural scaffold not observed among known Bcl-2 inhibitors. This work presents the structural optimization of this lead compound. By following the scaffold-hopping strategy, we have designed and synthesized a total of 82 compounds in three sets. All of the compounds were evaluated in a fluorescence-polarization binding assay to measure their binding affinities to Bcl-xL, Bcl-2, and Mcl-1. Some of the compounds with a 3-phenylthiophene-2-sulfonamide core moiety showed sub-micromolar binding affinities to Mcl-1 (Ki=0.3-0.4 μM) or Bcl-2 (Ki≈1 μM). They also showed obvious cytotoxicity on tumor cells (IC 50L in a similar mode to ABT-737. Several apoptotic assays conducted on HL-60 cells demonstrated that these compounds are able to induce cell apoptosis through the mitochondrial pathway. We propose that the compounds with the 3-phenylthiophene-2-sulfonamide core moiety are worth further optimization as effective apoptosis inducers with an interesting selectivity towards Mcl-1 and Bcl-2. Hopping to inhibition: Several sets of derivatives of a lead compound have been designed and synthesized by following the scaffold-hopping strategy, and active compounds containing a 3-phenylthiophene-2-sulfonamide core moiety have been obtained. The most potent compounds have sub-micromolar binding affinity to the antiapoptotic protein Mcl-1 and are effective apoptosis inducers in living cells.