RESUMEN
A series of 9α-hydroxyamino-parthenolides 3-10, 9ß-hydroxyamino-parthenolides 11-13 and 9α-hydroxy-1ß,10α-epoxyamino-parthenolides 15-19 were efficiently synthesized starting from 9α-hydroxyparthenolide 1 and 9ß-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.
Asunto(s)
Aminas/farmacología , Antineoplásicos/farmacología , Sesquiterpenos/farmacología , Aminas/química , Animales , Antineoplásicos/síntesis química , Antineoplásicos/química , Línea Celular Tumoral , Proliferación Celular/efectos de los fármacos , Relación Dosis-Respuesta a Droga , Ensayos de Selección de Medicamentos Antitumorales , Humanos , Células MCF-7 , Ratones , Conformación Molecular , Sesquiterpenos/química , Relación Estructura-ActividadRESUMEN
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 0.343â (3)â Å. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 18.12â (14)°. An intra-molecular O-Hâ¯N hydrogen bond occurs. The crystal structure features weak C-Hâ¯O inter-actions.
RESUMEN
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-Hâ¯N hydrogen bond between the hy-droxy group and a piperazine N atom. The crystal structure is built up by weak C-Hâ¯O inter-actions.
RESUMEN
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 [19.1â (3) and 16.2â (3)°]. An intra-molecular O-Hâ¯N hydrogen bond stabilizes the mol-ecular conformation. The crystal packing is stabilized by C-Hâ¯O hydrogen bonds.
RESUMEN
The title compound, C(19)H(29)NO(6), 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. In the crystal, weak C-Hâ¯O hydrogen bonds connect the mol-ecules into layers parallel to (001). An intra-molecular O-Hâ¯N hydrogen bond is also present.
RESUMEN
The title compound, C(25)H(34)N(2)O(6), 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 ten-membered ring adopts an approximate chair-chair conformation, while the piperazine ring displays a near regular chair conformation and the five-membered ring an envelope conformation with the C atom closest to the hy-droxy group forming the flap. The mol-ecular conformation is stabilized by an O-Hâ¯N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C-Hâ¯O inter-actions.
RESUMEN
The title compound, C(25)H(33)ClN(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 is built up from fused five- and ten-membered rings with two additional ep-oxy ring systems and a chloro-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 stabilized by an intra-molecular O-Hâ¯N hydrogen bond between the hy-droxy group and a piperazine N atom. The crystal structure is stabilized by weak C-Hâ¯O inter-actions.
RESUMEN
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-Hâ¯O hydrogen bonds connect mol-ecules into dimers that are inter-connected by C-Hâ¯O inter-actions, producing supramolecular chains along the b axis.
RESUMEN
The title compound, C(20)H(31)NO(4), 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 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 21.7â (4)°. The mol-ecular conformation is stabilized by an O-Hâ¯N hydrogen bond and the crystal structure is stabilized by weak inter-molecular C-Hâ¯O inter-actions.
RESUMEN
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-Hâ¯O hydrogen bonds connect mol-ecules into chains along [100]. Weak inter-molecular C-Hâ¯O hydrogen bonds are also present.
RESUMEN
The title compound, C(20)H(31)NO(5), 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 the pipyridin-1-yl-methyl group as a substituent. The ten-membered ring adopts an approximate chair-chair conformation, while the six- and five-membered rings display chair and envelope conformations, respectively. The dihedral angle between the mean planes of the ten-membered ring and the lactone ring is 20.8â (3)°. An intra-molecular O-Hâ¯N hydrogen-bond occurs. The crystal structure is stabilized by weak inter-molecular C-Hâ¯O hydrogen bonds.
RESUMEN
The title compound, C(19)H(29)NO(5), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-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 (morpholin-4-yl)methyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and the morpholine rings display approximate chair-chair and chair conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 27.93â (6)°. The crystal structure is stabilized by weak inter-molecular C-Hâ¯O hydrogen-bond inter-actions. An intra-molecular O-Hâ¯N hydrogen bond also occurs.
RESUMEN
The title compound, C(15)H(20)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 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 21.69â (10)°. In the crystal, mol-ecules are linked into chains propagating along the c axis by inter-molecular O-Hâ¯O hydrogen bonds; an intra-molecular O-Hâ¯O link also occurs.
RESUMEN
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 21.81â (9)°. An intra-molecular O-Hâ¯N hydrogen bond stabilizes the mol-ecular conformation. In the crystal, inter-molecular C-Hâ¯O inter-actions link the mol-ecules into chains parallel to the c axis.
RESUMEN
The title compound, C(15)H(18)O(3), 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 five-membered lactone ring has a twisted conformation, while the six- and five-membered rings display chair and envelope conformations, respectively. The dihedral angle between the two five-membered rings is 50.57â (11)°.
RESUMEN
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 0.443â (2) and 0.553â (2)â Å. The dihedral angle between the least-squares planes through the ten- and five-membered rings in the two mol-ecules are similar [22.54â (17) and 23.39â (14)°]. In the crystal, mol-ecules are linked by O-Hâ¯O, O-Hâ¯N and N-Hâ¯O hydrogen bonds.
RESUMEN
The title compound, C(19)H(29)O(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-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-1-ylmethyl group as a substituent. The five-membered lactone ring has an envelope conformation, whereas the ten-membered and pyrrolidine rings display approximate chair-chair and twisted conformations, respectively. The dihedral angle between the ten-membered ring and the lactone ring is 18.01â (19)°. An intra-molecular O-Hâ¯N hydrogen bond occurs. The crystal structure is stabilized by weak inter-molecular C-Hâ¯O hydrogen-bonding inter-actions.
RESUMEN
The title compound, C(15)H(21)ClO(4), was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-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 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 0.2325â (15)â 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 66.4â (2)°. In the crystal, mol-ecules are linked into chains propagating along the a axis by O-Hâ¯O hydrogen bonds.
RESUMEN
The title compound, C(18)H(20)O(3), a hemisynthetic product, was obtained by the reaction of benzoyl chloride and p-methoxy-thymol. The structure comprises two benzene rings bridged by a carboxyl group; the dihedral angle between the rings is 73.54â (8)°.
RESUMEN
The title compound, C(15)H(20)O(5) (systematic name: 5-hydroxy-1a,4a-dimethyl-7-methyleneperhydrodioxireno[5,6:9,10]cyclo-deca[1,2-b]furan-8-one), was obtained by the reaction of 3-chloro-perbenzoic acid with 9ß-hy-droxy-parthenolide. The five-membered ring adopts a twist conformation, whereas the ten-membered ring displays an approximate chair-chair conformation. In the crystal structure, mol-ecules are linked into chains propagating along the b axis by inter-molecular O-Hâ¯O hydrogen bonds.