Chemistry:Fostedil
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Short description: Chemical compound
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| Routes of administration | Oral |
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| Formula | C18NO3PS |
| Molar mass | 341.24 g·mol−1 |
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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.[1][2][3][4] It has antihypertensive and antiarrhythmic effects.[5][6][7]
Synthesis
Fostedil synthesis:[8]
- Treatment of benzanilide with phosphorus pentasulfide or Lawesson's reagent gives thioamide.
- Oxidative ring formation by reaction with potassium ferricyanide and base (presumably involving a free radical intermediate) constructs the benzothiazole ring.
- Bromination of this compound with N-bromosuccinimide produces bromomethyl intermediate.
- The synthesis of fostedil concludes with a Michaelis-Arbuzov reaction with triethyl phosphite.
See also
References
- ↑ Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. 1996. ISBN 0-412-46630-9. https://books.google.com/books?id=DeX7jgInYFMC&q=Fostedil&pg=PA931.
- ↑ "Ambulatory monitoring and exercise testing in the evaluation of a new long-acting calcium ion antagonist KB-944 (Fostedil) for the treatment of exertional angina pectoris". International Journal of Cardiology 9 (3): 289–302. November 1985. doi:10.1016/0167-5273(85)90027-0. PMID 3902675.
- ↑ "Vasodilator action of KB-944, a new calcium antagonist". Arzneimittel-Forschung 32 (9): 1037–1042. 1982. PMID 6890822.
- ↑ "Vasodilator mechanism of KB-944, a new calcium antagonist". Arzneimittel-Forschung 32 (9): 1043–1046. 1982. PMID 6890823.
- ↑ "Antihypertensive effect of KB-944, a new calcium antagonist, in conscious normotensive and hypertensive rats". Arzneimittel-Forschung 32 (9): 1047–1052. 1982. PMID 6890824.
- ↑ "Cardiac action of KB-944, a new calcium antagonist". Arzneimittel-Forschung 32 (9): 1053–1055. 1982. PMID 6890825.
- ↑ "Antiarrhythmic effect of KB-944, a new calcium antagonist. A comparison with verapamil and diltiazem". Arzneimittel-Forschung 32 (9): 1056–1059. 1982. PMID 6890826.
- ↑ "Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator". Journal of Medicinal Chemistry 29 (5): 820–825. May 1986. doi:10.1021/jm00155a037. PMID 3701791.
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