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Synfacts 2011(6): 0587-0587  
DOI: 10.1055/s-0030-1259891
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

n-Nitric Oxide Synthase Inhibitor

Contributor(s): Philip Kocienski
S. Hanessian*, E. Stoffman, X. Mi, P. Renton
Université de Montréal and NeurAxon Inc., Missiassauga, Canada
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Publication History

Publication Date:
19 May 2011 (online)

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Significance

N-Indolylamidines, such as G, are inhibitors of neuronal nitric oxide synthase (nNOS) and 5-HT1D/1B receptors. They are of interest for the treatment of migraine headaches. A key step in an enantioselective synthesis of the 3-pyrrolidinylindole core F is an organocatalytic asymmetric conjugate addition of 5-bromoindole (A) to an ­iminium ion generated from condensation of the MacMillan imidazolidinone C with the 4-amino-2-butenal derivative B.