13-(Imidazol-1-yl)-11,13-di-hydro-melampomagnolide B monohydrate.
The title compound, C18H24N2O4·H2O {systematic name: (1aR,7aS,8R,10aS,10bS,E)-5-hy-droxy-methyl-8-[(1H-imidazol-1-yl)meth-yl]-1a-methyl-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-9(1aH)-one monohydrate}, an imidazole derivative of melampomagnolide B was synthesized under Michael addition conditions. The mol-ecule is built up from fused ten-, five- (lactone) and three-membered (epoxide) rings. The inter-nal double bond of the ten-membered ring identifies it as the cis or E isomer. The lactone ring has an envelope-type conformation, with the (chiral) C atom opposite the lactone O atoms as the flap atom. In the crystal, O-H⋯O, O-H⋯N and weak C-H⋯O hydrogen bonds link the mol-ecules (along with water) into sheets parallel to the bc plane.
Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
Venumadhav
V
Janganati
Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
Narsimha Reddy
NR
Penthala
Department of Chemistry, University of Kentucky, Lexington KY 40506, USA.
Sean
S
Parkin
Department of Pharmaceutical Sciences, College of Pharmacy, University of Arkansas for Medical Sciences, Little Rock, AR 72205, USA.
Peter A
PA
Crooks