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'''Azosemide''' is a high-ceiling ] agent. '''Azosemide''' is a high-ceiling ] agent.
==Synthesis==
]


] of 2-fluoro-4-chloro-] ('''1''') followed by ammonolysis of the product gives ] ('''2'''). The regiochemistry of the next reaction, nucleophilic aromatic displacement, can be attributed in this case to the better leaving group properties of fluoride ions over chloride ions. Reaction with 2-methylaminothiophene thus gives '''3''' as the product. There is ample precedent to indicate that tetrazoles are bioisosteric with carboxylic acids, with the two groups showing quite comparable pKAs. Treatment with ] and ] leads to 1,3 addition of the elements of ] to the nitrile and the formation of a ] ring. This yields the high ceiling diuretic agent azosemide ('''4''').
==References== ==References==
{{Reflist|2}}
Popelak, A.; Lerch, A.; Stach, K.; Roesch, E.; Hardebeck, K.; German Offen., 1970, 815922; Chem. Abstr. 1970, 73, 45519.


] ]

Revision as of 14:40, 11 July 2015

Pharmaceutical compound
Azosemide
Structural formula of azosemide
Space-filling model of the azosemide molecule
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
  • none
Identifiers
IUPAC name
  • 2-chloro-5-(2H-tetrazol-5-yl)-4-benzenesulfonamide
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.044.121 Edit this at Wikidata
Chemical and physical data
FormulaC12H11ClN6O2S2
Molar mass370.84 g/mol g·mol
3D model (JSmol)
SMILES
  • O=S(=O)(N)c2c(Cl)cc(c(c1nnnn1)c2)NCc3sccc3
InChI
  • InChI=1S/C12H11ClN6O2S2/c13-9-5-10(15-6-7-2-1-3-22-7)8(12-16-18-19-17-12)4-11(9)23(14,20)21/h1-5,15H,6H2,(H2,14,20,21)(H,16,17,18,19)
  • Key:HMEDEBAJARCKCT-UHFFFAOYSA-N
  (what is this?)  (verify)

Azosemide is a high-ceiling diuretic agent.

Synthesis

Azosemide synthesis:

Chlorosulfonation of 2-fluoro-4-chloro-benzonitrile (1) followed by ammonolysis of the product gives sulfonamide (2). The regiochemistry of the next reaction, nucleophilic aromatic displacement, can be attributed in this case to the better leaving group properties of fluoride ions over chloride ions. Reaction with 2-methylaminothiophene thus gives 3 as the product. There is ample precedent to indicate that tetrazoles are bioisosteric with carboxylic acids, with the two groups showing quite comparable pKAs. Treatment with sodium azide and hydrochloric acid leads to 1,3 addition of the elements of hydrazoic acid to the nitrile and the formation of a tetrazole ring. This yields the high ceiling diuretic agent azosemide (4).

References

  1. A. Popelak et al., DE 1815922 ; eidem, U.S. patent 3,665,002 (1968, 1972 both to Boehringer, Mann.).
  2. DE 2353388 


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