Azosemide: Difference between revisions

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	==Synthesis==		==Synthesis==
	]

			]
	] of substituted ] () followed by ammonolysis of the product gives ] (). 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 () 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 '']''.

	==References==		==References==
			Popelak, A.; Lerch, A.; Stach, K.; Roesch, E.; Hardebeck, K.; German Offen., 1970, 815922; Chem. Abstr. 1970, 73, 45519.
	{{reflist}}

	]		]

Revision as of 09:20, 13 January 2015

Pharmaceutical compound

Azosemide
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	none
Identifiers
IUPAC name 2-chloro-5-(2H-tetrazol-5-yl)-4-benzenesulfonamide
CAS Number	27589-33-9
PubChem CID	2273
ChemSpider	2186
UNII	MR40VT1L8Z
KEGG	D01323
ChEBI	CHEBI:31248
ChEMBL	ChEMBL1097235
CompTox Dashboard (EPA)	DTXSID7046910
ECHA InfoCard	100.044.121
Chemical and physical data
Formula	C₁₂H₁₁ClN₆O₂S₂
Molar mass	370.84 g/mol g·mol
3D model (JSmol)	Interactive image
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
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Azosemide is a high-ceiling diuretic agent.

Popelak, A.; Lerch, A.; Stach, K.; Roesch, E.; Hardebeck, K.; German Offen., 1970, 815922; Chem. Abstr. 1970, 73, 45519.

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