Abstract
The title compound, C19H22N2O3, {systematic name (1aR,4E,7aS,8E,10aS,10bR)-1a,5-dimethyl-8-[(pyrimidin-5-yl)-methylid-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} was obtained from the reaction of parthenolide [systematic name (1aR,7aS,10aS,10bR,E)-1a,5-dimethyl-8-methyl-ene-2,3,6,7,7a,8,10a,10b-octa-hydro-oxireno[2',3':9,10]cyclodeca-[1,2-b]furan-9(1aH)-one] with 5-bromo-pyrimidine under Heck reaction conditions, and was identified as an E isomer. The mol-ecule possesses ten-, five- (lactone) and three-membered (epoxide) rings with a pyrimidine group as a substituent. The ten-membered ring displays an approximate chair-chair conformation, while the lactone ring shows a flattened envelope-type conformation. The dihedral angle between the pyrimidine moiety and the lactone ring system is 29.43 (7)°.
Highlights
Parthenolide (PTL) is a sesquiterpene lactone known to significantly target cancer stem cells, which are the putative roots of all types of cancer (Gopal et al, 2007)
PTL was discovered to be capable of inducing robust apoptosis in primary acute myelogenous leukemia (AML) cells (Guzman et al, 2007), proving to be effective among all subpopulations within primary AML specimens, including leukemia stem cells (LSCs)
There are a few C—HÁ Á ÁN and C—HÁ Á ÁO short contacts, but none that have the right geometry to be considered as non-classical hydrogen bonds
Summary
Parthenolide (PTL) is a sesquiterpene lactone known to significantly target cancer stem cells, which are the putative roots of all types of cancer (Gopal et al, 2007). PTL exhibits a wide range of biological activities, such as anti-inflammatory, anti-bacterial, antifungal, and cytotoxic properties (Picman, 1986). Han et al (2009) reported on bioactive derivatives of Heck products of PTL. Penthala et al (2014a) reported the anti-cancer activity of PTL–Heck products. We (Penthala et al, 2014b) reported the crystal structure of 13-{4-[Z–2-cyano-2-(3,4,5trimethoxyphenyl)ethenyl]phenyl} parthenolide, an analog of PTL, which was found to have the E configuration at C-13. The interesting biological properties of PTL directed our attention to design and synthesize additional bioactive derivatives. E71, 1536–1538 research communications bond, a single crystal X-ray structure determination has been carried out
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