Mepindolol
Appearance
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ECHA InfoCard | 100.041.650 |
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Formula | C15H22N2O2 |
Molar mass | 262.353 g·mol−1 |
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Chirality | Racemic mixture |
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Mepindolol (Betagon) is a non-selective beta blocker. It is used to treat glaucoma.[1]
Synthesis
[edit]The first reported synthesis of mepindolol in 1971 used 4-hydroxy-2-methylindole {9) with epichlorohydrin and then isopropylamine to add the sidechain which was known to produce beta blockers, by analogy with drugs discovered by Imperial Chemical Industries, such as propanolol.[2] The requisite intermediate was synthesized in a multi-step procedure from 4-benzyloxyindole-2-carboxylic acid (1) which was converted into (9) by conventional chemistry.[3][4]
See also
[edit]References
[edit]- ^ Schmid MG, Gecse O, Szabo Z, Kilár F, Gübitz G, Ali I, et al. (September 2001). "Comparative study of the chiral resolution of β-blockers on cellulose tris (3,5-dimethyl-phenylcarbamate) phases in normal and reversed phase modes". Journal of Liquid Chromatography & Related Technologies. 24 (16): 2493–2504. doi:10.1081/JLC-100105955.
- ^ Lednicer D (1998). Strategies for Organic Drug Synthesis and Design. Canada: John Wiley & Sons. pp. 37–41. ISBN 0-471-19657-6.
- ^ Seemann F, Wiskott E, Niklaus P, Troxler F (1971). "Beiträge zur Chemie der 4-Hydroxyindol-Verbindungen 10. Mitteilung über synthetische indolverbindungen" [Contributions to the chemistry of 4-hydroxyindole compounds 10. Report on synthetic indole compounds]. Helvetica Chimica Acta (in German). 54 (8): 2411–2419. doi:10.1002/hlca.19710540805.
- ^ "Mepindolol". Pharmaceutical Substances. Georg Thieme Verlag KG. Retrieved 2024-06-30.