Abstract
The title compound, C21H25NO3 [systematic name: (1aR,4E,7aS,8E,10aS,10bR)-8-(2-amino-benzyl-idene)-1a,5-dimethyl-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-9(1aH)-one], was synthesized by the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bS,E)-1a,5-dimethyl-8-methyl-ene-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclo-deca-[1,2-b]furan-9(1aH)-one] with 2-iodo-aniline via Heck reaction conditions. The mol-ecule is composed of fused ten-, five- (lactone), and three-membered (epoxide) rings. The lactone ring shows a flattened envelope-type conformation (r.m.s. deviation from planarity = 0.0477 Å), and bears a 2-amino-benzyl-idene substituent that is disordered over two conformations [occupancy factors 0.901 (4) and 0.099 (4)]. The ten-membered ring has an approximate chair-chair conformation. The dihedral angle between the 2-amino-benzyl-idine moiety (major component) and the lactone ring (mean plane) is 59.93 (7)°. There are no conventional hydrogen bonds, but there are a number of weaker C-H⋯O-type inter-actions.
Highlights
Y, Àz) stacking of lactone groups parallel to the b axis (Fig. 2)
There are no conventional hydrogen bonds, but there are a number of weaker C—HÁ Á ÁO-type interactions
Sesquiterpene lactones (SLs) are a large family of natural products that have been widely investigated for their anticancer activity
Summary
Sesquiterpene lactones (SLs) are a large family of natural products that have been widely investigated for their anticancer activity. Previous work from our laboratory (Nasim & Crooks, 2008) reported the amino analogues of PTL as anti-leukemic agents, and a water-soluble analogue of PTL, dimethylaminoparthenolide (DMAPT), has advanced into clinical studies (Ghantous et al, 2010). Kempema et al (2015) have reported C1 to C10-modified PTL analogues as anti-leukemic agents. Han et al (2009) have reported Heck products of PTL as anti-cancer agents. In continuing efforts from our group, Penthala et al (2014a) reported Heck products of PTL and Melampomagnolide B as anti-cancer agents. The distance between planes of adjacent lactone rings is half the b-axis length
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