1571902-04-9

Basic information

• Product Name: 1-(3-chloro-4-fluorophenyl)-5-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1H-tetrazole
• Synonyms: 1-(3-chloro-4-fluorophenyl)-5-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1H-tetrazole
• CAS NO: 1571902-04-9
• Molecular Weight: 378.771
• Mol File: 1571902-04-9.mol

Chemical Properties

• CAS DataBase Reference: 1-(3-chloro-4-fluorophenyl)-5-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1H-tetrazole(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(3-chloro-4-fluorophenyl)-5-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1H-tetrazole(1571902-04-9)
• EPA Substance Registry System: 1-(3-chloro-4-fluorophenyl)-5-(2,2-dioxido-1,2-benzoxathiin-6-yl)-1H-tetrazole(1571902-04-9)

Safety Data

• Hazardous Substances Data: 1571902-04-9(Hazardous Substances Data)

Upstream product

• 1571901-95-5 2-formyl-4-iodophenyl methanesulfonate 
• 351373-03-0 1-(3-chloro-4-fluorophenyl)-1H-1,2,3,4-tetrazole 
• 1571901-96-6 6-iodo-1,2-benzoxathiine 2,2-dioxide 
• 1761-62-2 5-iodosalicyclaldehyde 

Relevant articles and documents

Sulfocoumarins as dual inhibitors of human carbonic anhydrase isoforms IX/XII and of human thioredoxin reductase

The hypothesis that sulfocoumarin acting as inhibitors of human carbonic anhydrase (CA, EC 4.2.1.1) cancer-associated isoforms hCA IX and–hCA XII is being able to also inhibit thioredoxin reductase was verified and confirmed. The dual targeting of two cancer cell defence mechanisms, i.e. hypoxia and oxidative stress, may both contribute to the observed antiproliferative profile of these compounds against many cancer cell lines. This unprecedented dual anticancer mechanism may lead to a new approach for designing innovative therapeutic agents.

Synthesis of 6-tetrazolyl-substituted sulfocoumarins acting as highly potent and selective inhibitors of the tumor-associated carbonic anhydrase isoforms IX and XII

A series of 6-substituted sulfocoumarins incorporating substituted-1,2,3,4- tetrazol-5-yl moieties were synthesized by reaction of 6-iodo-sulfocoumarin and the corresponding tetrazole via the CH activation reaction. The new sulfocoumarins incorporating alkyl and substituted aryl moieties at the 1-position of the tetrazole, were investigated for the inhibition of four human (h) carbonic anhydrase (hCA, EC 4.2.1.1) isoforms, the cytosolic hCA I and II; and the transmembrane, tumor-associated hCA IX and XII. The tetrazole- substituted sulfocoumarins did not inhibit the ubiquitous, off-target cytosolic isoforms (KIs >10 μM) but showed effective inhibition against the two transmembrane CAs, with KIs ranging from 6.5 to 68.6 nM against hCA IX, and between 4.3 and 59.8 nM against hCA XII. As hCA IX and XII are validated anti-tumor targets, such prodrug, isoform-selective inhibitors as the sulfocoumarins reported here, may be useful for identifying suitable drug candidates for clinical trials.