Fostedil

Fostedil

File:Fostedil structure.png
Systematic (IUPAC) name
diethyl [4-(1,3-benzothiazol-2-yl)benzyl]phosphonate
Clinical data
Legal status	Uncontrolled
Routes of administration	Oral
Identifiers
CAS Number	75889-62-2
ATC code	none
PubChem	CID: 53421
ChemSpider	48253
UNII	D41WS786UL Y
KEGG	D04260
ChEMBL	CHEMBL39516
Chemical data
Formula	C18NO3PS
Molecular mass	361.40 g/mol
SMILES O=P(OCC)(OCC)Cc3ccc(c1nc2ccccc2s1)cc3

Fostedil (A-53,986, KB-944) is a vasodilator acting as a calcium channel blocker which was under development for the treatment of heart conditions such as angina pectoris but was never marketed. It has antihypertensive and antiarrhythmic effects.

Synthesis

File:Fostedil synthesis.png

Fostedil synthesis:

1. Treatment of benzanilide with phosphorus pentasulfide or Lawesson's reagent gives thioamide.
2. Oxidative ring formation by reaction with potassium ferricyanide and base (presumably involving a free radical intermediate) constructs the benzothiazole ring.
3. Bromination of this compound with N-bromosuccinimide produces bromomethyl intermediate.
4. The synthesis of fostedil concludes with a Michaelis-Arbuzov reaction with triethyl phosphite.

See also

• Calcium channel blocker