Just curious whatall the group opinion would be of this as a target. A guanadine group is a nitrogen, connected to a carbon that is double bonded to a nitrogen and single bonded to another nitrogen. Resonance structures may be drawn.
Proposal:
MDA + bis-Bocthiourea, TEA/HgCl2/DMF 0 C to RT 2H dilute EtOAc, filter celite, rotovap ~45 C. Chromatograph directly with a good layer of sand. Cleave the Boc groups with, say 4 N HCl in dioxane (10-15min), evaporate, take up in water nuet to pH 7 with AmBic, down a MeOH washed then water washed C-18 column, elute with water then water/MeOH if needed, lyophilize appropriate fractions.
Product: Guanadine derive of MDA ta da!!
Would this be interesting? Who can speculate on the SAR of this substitution? All around the ring, length of butyl chain, all this is (has been, will be) explored. But what of the amino/methyl amino moiety?
One might also use Monomethyl-bis-Bocthiourea, and get out the methylated guanadino derivative.
Maybe the MD ring has some prob with that strong of cleavage conditions. Hopefully not.
Anywho, what are the thoughts on binding this bugger to the appropriate receptor?