Abstract
The ergot alkaloids are an important class of medicinally useful substances and this report describes the high specific activity tritium labelling of two dihydro derivatives; namely, dihydroergotamine and dihydrobromocriptine. The former was prepared by the direct tritiation of ergotamine itself. However, efforts to perform an analogous direct tritiation on bromocriptine were unsuccessful and a multistep synthesis was required.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Staniek A, Bouwmeester H, Fraser PD, Kayser O, Martens S, Tissier A, Van der Krol S, Wessjohann L, Warzecha H (2014) Natural products—learning chemistry from plants. Biotechnol J 9:326–336
Christopoulos S, Szilagyi A, Kahn SR (2001) Saint-Anthony’s fire. Lancet 358:1694
Rimar Y, Rimar D (2003) Witches saints and other diseases. Harefuah 142:383–386
Egan JA, Seguin RJ, Filer CN (2015) Tritiation and characterization of several biologically active nightshade alkaloids. J Radioanal Nucl Chem 303:2439–2443
Berstein IA, Bennett W, Fields M (1952) Tritiation of multiple bonds—synthesis of tritiated styrene. J Am Chem Soc 74:5763–5764
Maier W, Erge D, Groeger D (1983) Further studies on cell-free biosynthesis of ergotamine in Claviceps purpurea. FEMS Microbiol Lett 20:233–236
Silberstein SD, Kori SH (2013) Dihydroergotamine: a review of formulation approaches for the acute treatment of migraine. CNS Drugs 27:385–394
Mrkvicka V, Lycka A, Rudolf O, Klasek A (2010) Reaction of 3-aminoquinoline-2,4-diones with isothiocyanic acid—an easy pathway to thioxo derivatives of imidazo[1, 5-c]quinazolin-5-ones and imidazo[4,5-c]quinolin-4-ones. Tetrahedron 66:8441–8445
Stoll A, Hofmann A (1979) In: Manske RHF (ed) The alkaloids, Chap 21, vol 8. Academic Press, pp 726–783
Young JF, Osborn JA, Jardine FH, Wilkinson G (1965) Hydride intermediates in homogeneous hydrogenation reactions of olefins and acetylenes using rhodium catalysts. JCS Chem Commun 7:131–132
Jourdant A, Gonzalez-Zamora E, Zhu J (2002) Wilkinson’s catalyst catalyzed selective hydrogenation of olefin in the presence of an aromatic nitro function: a remarkable solvent effect. J Org Chem 67:3163–3164
Egan JA, Nugent RP, Filer CN (2004) Potent antiviral agent WIN 54954: high specific activity labelling with tritium. Appl Radiat Isot 60:851–853
Birch AJ, Walker KAM (1966) Aspects of catalytic hydrogenation with a soluble catalyst. J Chem Soc C 1894–1896
Harmon RE, Parsons JL, Cooke DW, Gupta SK, Schoolenberg J (1969) Homogeneous catalytic hydrogenation of unsaturated organic compounds. J Org Chem 34:3684–3685
Seifert K, Meyer H, Hartling S, Johne S (1989) Nuclear magnetic resonance spectroscopy of some dihydrolysergic acid derivatives. Tetrahedron 45:7291–7300
Hofmann A, Troxler F (1950) Halogenated derivatives of lysergic acid, isolysergic acid and their derivatives and a process of making same. US Patent 2,516,002
Acknowledgments
We would like to acknowledge the contribution of Dr. Puliyur Srinivasan for obtaining the tritium NMR spectrum.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Egan, J.A., Nugent, R.P. & Filer, C.N. CNS active ergot alkaloid dihydro derivatives: tritium labelling and characterization. J Radioanal Nucl Chem 310, 823–827 (2016). https://doi.org/10.1007/s10967-016-4815-4
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10967-016-4815-4