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The ten-membered ring in the title molecule, C25H29ClN2O7, adopts an approximate chair–chair conformation, whereas the five-membered furan and pyrazole rings display envelope conformations. The mean plane of the furan ring is almost perpendicular to that of the pyrazole ring, as indicated by the dihedral angle between them of 86.45 (9)°. The pyrazole ring is slightly inclined to the plane of the attached phenyl ring, subtending a dihedral angle of 16.88 (8)°. The conformation of the molecule is stabilized by six intramolecular hydrogen bonds and crystal cohesion is ensured by five C—H...O hydrogen bonds, in addition to C—H...π interactions.

The ten-membered ring in the title mol-ecule, C

The chemoselectivity and stereospecificity of the addition of the morpholine and the meta-chloroperoxybenzoic acid (m-CPBA) onto 9α-hydroxyparthenolide were studied using Density Functional Theory (DFT) calculations with the B3LYP/6-311+G(d,p) computational level within the Molecular Electron Density Theory (MEDT), to demonstrate the key role of the Global Electron Density Transfer (GEDT) and to examine the polar character of these reactions. This work is divided into two parts; the first part concerns the reaction between the morpholine and the 9α-hydroxyparthenolide. The second part deals with the epoxidation of the 9α-hydroxyparthenolide by m-CPBA followed by the addition of the morpholine to the major product resulting from the epoxidation step. The obtained results show that the reaction between the morpholine and the 9α-hydroxyparthenolide takes place on the double bond C3=C4. On the other hand, when 9α-hydroxyparthenolide is attacked by m-CPBA, the epoxidation reaction is carried out on the double bond C1=C2.

A series of novel spiropyrazoles and spiroisoxazolines was efficiently synthesized. Structural modifications were performed at the C-9 and C-13 positions of 9α- and 9β-hydroxyparthenolide, which were isolated from the aerial parts of Anvillea radiata. The structures and stereochemistry of the cycloadducts were fully established by spectroscopic methods including X-ray diffraction data.

A series of 9α-hydroxyamino-parthenolides 3-10, 9β-hydroxyamino-parthenolides 11-13 and 9α-hydroxy-1β,10α-epoxyamino-parthenolides 15-19 were efficiently synthesized starting from 9α-hydroxyparthenolide 1 and 9β-hydroxyparthenolide 2, which were isolated from Anvillea radiata. Compounds 1-13 and 15-19 were evaluated for their in vitro anticancer activity by the MTT colorimetric assay against one murine and six human cancer cell lines. This work provides new details about the structural requisites for anticancer activity.

The catalytic acid rearrangement of 9α-hydroxyparthenolide (1), the main constituent of Anvillea radiata, has been studied. Several new sesquiterpene compounds were obtained and their structures were fully elucidated. A mechanism to explain the formation of these compounds is proposed.

The title compound, C25H33BrN2O4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts ofAnvillea radiata. The molecule is built up from two fused five- and ten-membered rings with an additional epoxy ring system and a bromophenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. An intramolecular O—H...N hydrogen bond stabilizes the molecular conformation. The crystal packing features C—H...O hydrogen bonds, which link the molecules into zigzag chains running along theb-axis direction.

The title compound, C(25)H(33)FN(2)O(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The asymmetric unit contains two independent mol-ecules. In each mol-ecule, the ten-membered ring displays an approximative chair-chair conformation. Each of the piperazine rings adopts a perfect chair conformation, while both lactone rings show an envelope conformation, one with the C atom bearing the piperazin-1-ylmethyl group as the flap, the other with the junction C atom not attached to the ring O atom as the flap. The dihedral angles between the least-squares planes through the ten- and five-membered rings in the two mol-ecules are similar [19.1 (3) and 16.2 (3)°]. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation. The crystal packing is stabilized by C-H⋯O hydrogen bonds.

The title compound, C(15)H(18)O(3), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The seven-membered ring of the title compound shows a chair conformation, while the five-membered rings exibit different conformations, viz a twisted one for the lactone ring and an envelope conformation for the other five-membered ring with the C atom closest to the hydroxy group forming the flap. In the crystal, O-H⋯O hydrogen bonds connect mol-ecules into dimers that are inter-connected by C-H⋯O inter-actions, producing supramolecular chains along the b axis.

The title compound, C15H21ClO4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from fused five- and ten-membered rings. The five-membered lactone ring has an envelope conformation with the flap atom, C(H)-C-C(H), displaced by 0.2325 (15) Å from the mean plane through the remaining four atoms, whereas the ten-membered ring displays an approximate chair–chair conformation. The dihedral angle between the two rings is 66.4 (2)°. In the crystal, molecules are linked into chains propagating along the a axis by O—H...O hydrogen bonds.

The title compound, C(25)H(34)N(2)O(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule contains a fused five- and ten-membered ring system. The ten-membered ring adopts an approximate chair-chair conformation, while the five-membered ring is in an envelope conformation, with the C atom closest to the hy-droxy group forming the flap. The piperazine ring is in a chair conformation. In the crystal, O-H⋯O hydrogen bonds connect mol-ecules into chains along [100]. Weak inter-molecular C-H⋯O hydrogen bonds are also present.

The title compound, C15H20O4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The seven-membered ring has a chair conformation, while the five-membered rings display twisted conformations. The dihedral angle between the seven-membered ring and the lactone ring is 21.69 (10)°. In the crystal, molecules are linked into chains propagating along the c axis by intermolecular O—H...O hydrogen bonds; an intramolecular O—H...O link also occurs.

The title compound, C25H34N2O5, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one), which in turn was isolated from the chloroform extract of the aerial parts ofAnvillea radiata. The molecule comprises a ten-membered ring fused to a five-membered ring with an additional epoxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hydroxyphenyl-piperazin-1-ylmethyl substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. Two C atoms in the phenyl ring and the O atom of the hydroxyl group are disordered over two sites, with an occupancy ratio of 0.53 (5):0.47 (5). An intramolecular O—H...N hydrogen-bond stabilizes the molecular conformation. In the crystal, C—H...O hydrogen bonds link the molecules into zigzag chains running along thea-axis direction.

The title compound, C25H33ClN2O5, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts ofAnvillea radiata. The molecule is built up from fused five- and ten-membered rings with two additional epoxy ring systems and a chlorophenylpiperazine group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hydroxy group forming the flap. The molecular conformation is stabilized by an intramolecular O—H...N hydrogen bond between the hydroxy group and a piperazine N atom. The crystal structure is stabilized by weak C—H...O interactions.

The title compound, C(26)H(36)N(2)O(6), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five- and ten-membered rings with two additional ep-oxy ring systems and a meth-oxy-phenyl-piperazine group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring shows an envelope conformation with the C atom closest to the hy-droxy group forming the flap. The mol-ecular conformation is determined by an O-H⋯N hydrogen bond between the hy-droxy group and a piperazine N atom. The crystal structure is built up by weak C-H⋯O inter-actions.

The title compound, C(26)H(36)N(2)O(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), wich was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from fused five- and ten-membered rings with the meth-oxy-phenyl-piperazine group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the piperazine ring displays a chair conformation and the five-membered ring a flattened envelope conformation; the C(H)-C-C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.343 (3) Å. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 18.12 (14)°. An intra-molecular O-H⋯N hydrogen bond occurs. The crystal structure features weak C-H⋯O inter-actions.

The title compound, C(19)H(29)NO(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methyl-ene-3,14-dioxatricyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule is built up from two fused five- and ten-membered rings with the (pyrrolidin-4-yl)methyl group as a substituent. The two five-membered ring display the same envelope conformations, whereas the ten-membered ring adopts an approximate chair-chair conformation. The dihedral angle between the ten-membered ring and the lactone ring is 21.81 (9)°. An intra-molecular O-H⋯N hydrogen bond stabilizes the mol-ecular conformation. In the crystal, inter-molecular C-H⋯O inter-actions link the mol-ecules into chains parallel to the c axis.

The title compound, C25H34N2O5, was synthesized from 9α-hy­droxy­parthenolide (9α-hy­droxy-4,8-dimethyl-12-methyl­ene-3,14-dioxatricyclo­[9.3.0.02,4]tetra­dec-7-en-13-one), which was isolated from the chloro­form extract of the aerial parts of Anvillea radiata. The mol­ecule contains a fused five- and ten-membered ring system. The ten-membered ring adopts an approximate chair–chair conformation, while the five-membered ring is in an envelope conformation, with the C atom closest to the hy­droxy group forming the flap. The piperazine ring is in a chair conformation. In the crystal, O—H⋯O hydrogen bonds connect mol­ecules into chains along [100]. Weak inter­molecular C—H⋯O hydrogen bonds are also present.

The title compound, C20H31NO4, was synthesized from 9α-hydroxyparthenolide (9α-hydroxy-4,8-dimethyl-12-methylen-3,14-dioxa-tricyclo[9.3.0.02,4]tetradec-7-en-13-one), which was isolated from the chloroform extract of the aerial parts of Anvillea radiata. The molecule is built up from fused five-and ten-membered rings with the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair–chair conformation, while the six-membered ring display a chair conformation and the five-membered ring an envelope conformation with the C(H)–C–C(H) atom at the flap. The dihedral angle between the ten-membered ring and the lactone ring is 21.7 (4)°. The molecular conformation is stabilized by an O—H...N hydrogen bond and the crystal structure is stabilized by weak intermolecular C—H...O interactions.

The title compound, C(21)H(27)NO(4), was synthesized from 9α-hy-droxy-parthenolide, which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The asymmetric unit contains two independent mol-ecules. In each, the ten-membered ring displays an approximative chair-chair conformation. Each of the five-membered rings adopts a flattened envelope conformation, the C(H)-C-C(H) atoms representing the flap lie out of the mean plane through the remaining four atoms by 0.443 (2) and 0.553 (2) Å. The dihedral angle between the least-squares planes through the ten- and five-membered rings in the two mol-ecules are similar [22.54 (17) and 23.39 (14)°]. In the crystal, mol-ecules are linked by O-H⋯O, O-H⋯N and N-H⋯O hydrogen bonds.

The title compound, C(17)H(22)O(6), was semi-synthesized from 9-hy-droxy-arthenolide, which was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule contains fused five- and ten-membered rings: the five-membered lactone ring has a twisted conformation, whereas the ten-membered ring displays an approximate chair-chair conformation. The dihedral angle between the rings is 24.76 (9)°.

The title compound, C18H20O3, a hemisynthetic product, was obtained by the reaction of benzoyl chloride and p-methoxythymol. The structure comprises two benzene rings bridged by a carboxyl group; the dihedral angle between the rings is 73.54 (8)°.