Fostedil
Chemical compound
- none
- In general: uncontrolled
- diethyl [4-(1,3-benzothiazol-2-yl)benzyl]phosphonate
- 75889-62-2
- 53421
- 48253
- D41WS786UL
- D04260
- ChEMBL39516
- DTXSID70226811
- Interactive image
- 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.[1][2][3][4] It has antihypertensive and antiarrhythmic effects.[5][6][7]
Synthesis
- 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
- ^ Triggle DJ (1996). Dictionary of Pharmacological Agents. Boca Raton: Chapman & Hall/CRC. ISBN 0-412-46630-9.
- ^ Khurmi NS, Bowles MJ, O'Hara MJ, Lahiri A, Raftery EB (November 1985). "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. doi:10.1016/0167-5273(85)90027-0. PMID 3902675.
- ^ Morita T, Yoshino K, Kanazawa T, Ito K, Nose T (1982). "Vasodilator action of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1037–1042. PMID 6890822.
- ^ Morita T, Kanazawa T, Ito K, Nose T (1982). "Vasodilator mechanism of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1043–1046. PMID 6890823.
- ^ Morita T, Kanazawa T, Ito K, Nose T (1982). "Antihypertensive effect of KB-944, a new calcium antagonist, in conscious normotensive and hypertensive rats". Arzneimittel-Forschung. 32 (9): 1047–1052. PMID 6890824.
- ^ Morita T, Ito K, Nose T (1982). "Cardiac action of KB-944, a new calcium antagonist". Arzneimittel-Forschung. 32 (9): 1053–1055. PMID 6890825.
- ^ Yoshidomi M, Sukamoto T, Morita T, Ito K, Nose T (1982). "Antiarrhythmic effect of KB-944, a new calcium antagonist. A comparison with verapamil and diltiazem". Arzneimittel-Forschung. 32 (9): 1056–1059. PMID 6890826.
- ^ Yoshino K, Kohno T, Uno T, Morita T, Tsukamoto G (May 1986). "Organic phosphorus compounds. 1. 4-(Benzothiazol-2-yl)benzylphosphonate as potent calcium antagonistic vasodilator". Journal of Medicinal Chemistry. 29 (5): 820–825. doi:10.1021/jm00155a037. PMID 3701791.
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