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10?-Hy-droxy-13-{[4-(2-hy-droxy-phen-yl)piperazin-1-yl]meth-yl}-4,9-dimethyl-3,8,15-trioxatetra-cyclo-[10.3.0.0(2,4).0(7,9)]penta-decan-14-one.

ABSTRACT: The title compound, C(25)H(34)N(2)O(6), was synthesized from 9?-hy-droxy-parthenolide (9?-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-H?N hydrogen bond, which generates an S(7) loop, and the crystal structure features weak C-H?O inter-actions.

SUBMITTER: Moumou M

PROVIDER: S-EPMC3344453 | biostudies-literature | 2012 May

REPOSITORIES: biostudies-literature

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10α-Hy-droxy-13-{[4-(2-hy-droxy-phen-yl)piperazin-1-yl]meth-yl}-4,9-dimethyl-3,8,15-trioxatetra-cyclo-[10.3.0.0(2,4).0(7,9)]penta-decan-14-one.

Moumou Mohamed M Benharref Ahmed A El Ammari Lahcen L Adil Mina M Berraho Moha M

Acta crystallographica. Section E, Structure reports online 20120406 Pt 5

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-dro ...[more]

PMID: 22590215

Similar Datasets

10?-Hy-droxy-4,9-dimethyl-13-[(4-phenyl-piperazin-1-yl)meth-yl]-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]tetra-decan-14-one.

Project description:The title compound, C(25)H(34)N(2)O(5), was synthesized from 9?-hy-droxy-parthenolide (9?-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.

| S-EPMC3247384 | biostudies-literature

10?-Hy-droxy-4,9-dimethyl-13-(morph-o-lin-4-ylmeth-yl)-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]penta-decan-14-one.

Project description:The title compound, C(19)H(29)NO(6), was synthesized from 9?-hy-droxy-parthenolide (9?-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-H?O hydrogen bonds connect the mol-ecules into layers parallel to (001). An intra-molecular O-H?N hydrogen bond is also present.

| S-EPMC3254508 | biostudies-literature

(1S,2R,3R,6R,7S,8R,10S,11S)-13-{[4-(4-Chloro-phen-yl)piperazin-1-yl]meth-yl}-10-hy-droxy-4,9-dimethyl-3,8,15-trioxatetra-cyclo-[10.3.0.0(2,4).0(7,9)]penta-decan-14-one.

Project description: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-H⋯N hydrogen bond between the hy-droxy group and a piperazine N atom. The crystal structure is stabilized by weak C-H⋯O inter-actions.

| S-EPMC3344091 | biostudies-literature

10?-Hy-droxy-13-{[4-(4-meth-oxy-phen-yl)piperazin-1-yl]meth-yl}-4,9-dimethyl-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]penta-decan-14-one.

Project description:The title compound, C(26)H(36)N(2)O(6), was synthesized from 9?-hy-droxy-parthenolide (9?-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.

| S-EPMC3295488 | biostudies-other

10?-Hy-droxy-4,9-dimethyl-13-[(pyrrol-idin-1-yl)meth-yl]-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]penta-decan-14-one.

Project description:The title compound, C(19)H(29)NO(5), was synthesized from 9?-hy-droxy-parthenolide (9?-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.

| S-EPMC3151905 | biostudies-other

10?-Hy-droxy-4,9-dimethyl-13-(pipyridin-1-ylmethyl)-3,8,15-trioxatetra-cyclo-[10.3.0.0.0]tetra-decan-14-one.

Project description:The title compound, C(20)H(31)NO(5), was synthesized from 9?-hy-droxy-parthenolide (9?-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 20.8?(3)°. An intra-molecular O-H?N hydrogen-bond occurs. The crystal structure is stabilized by weak inter-molecular C-H?O hydrogen bonds.

| S-EPMC3247403 | biostudies-literature

1-[4-(4-Hy-droxy-phen-yl)piperazin-1-yl]ethanone.

Project description:In the title compound, C12H16N2O2, the piperazine ring has a chair conformation. The dihedral angle between the mean planes of the benzene ring and the acetyl group is 48.7?(1)°. In the crystal, mol-ecules are linked via O-H?O hydrogen bonds, forming chains propagating along [010].

| S-EPMC3884329 | biostudies-literature

N-{2-[4-(2-Hy-droxy-eth-yl)piperazin-1-yl]eth-yl}phthalimide.

Project description:In the title compound, C(16)H(21)N(3)O(3), the piperazine ring adopts a chair conformation, with its N-C bonds in pseudo-equatorial orientations. In the crystal, mol-ecules are linked by O-H?N hydrogen bonds, generating C(5) chains propagating in [101]. Weak aromatic ?-? stacking inter-actions also occur [centroid-centroid separation = 3.899?(1)?Å].

| S-EPMC3254512 | biostudies-literature

7,9-Bis(hy-droxy-meth-yl)-7H-purine-2,6,8(1H,3H,9H)trione.

Project description:The structure of the title uric acid derivative, C(7)H(8)N(4)O(5), from human kidney stones, is characterized by the C and O atoms of one of the two hy-droxy-methyl groups being disordered nearly equally over three different sites. In the crystal, mol-ecules are connected by a three-dimensional hydrogen-bonding scheme though they look stacked in planes nearly parallel to ([Formula: see text]04).

| S-EPMC3120625 | biostudies-literature

(2Z,4E)-1-(5-Fluoro-2-hy-droxy-phen-yl)-5-(4-fluoro-phen-yl)-3-hy-droxy-penta-2,4-dien-1-one.

Project description:In the title mol-ecule, C17H12F2O3, the dihedral angle between the benzene rings is 8.6?(2)°. In the crystal, two pairs of O-H?O hydrogen bonds connect the mol-ecules into inversion dimers. In addition, weak C-H?F hydrogen bonds link the dimers into a two-dimensional network parallel to (10-4). The carbonyl O atom is an acceptor for two weak intra-molecular hydrogen bonds.

| S-EPMC3914111 | biostudies-literature

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