RESUMEN
We report the synthesis of two novel halogenated nitro-arylhimachalene derivatives: 2-bromo-3,5,5,9-tetramethyl-1-nitro-6,7,8,9-tetrahydro-5H-benzo[7]annulene (bromo-nitro-arylhimachalene) and 2-chloro-3,5,5,9-tetramethyl-1,4-dinitro-6,7,8,9-tetrahydro-5H-benzo[7]annulene (chloro-dinitro-arylhimachalene). These compounds were derived from arylhimachalene, an important sesquiterpene component of Atlas cedar essential oil, via a two-step halogenation and nitration process. Characterization was performed using 1H and 13C NMR spectrometry, complemented by X-ray structural analysis. Quantum chemical calculations employing density functional theory (DFT) with the Becke3-Lee-Yang-parr (B3LYP) functional and a 6-31++G(d,p) basis set were conducted. The optimized geometries of the synthesized compounds were consistent with X-ray structure data. Frontier molecular orbitals and molecular electrostatic potential (MEP) profiles were identified and discussed. DFT reactivity indices provided insights into the compounds' behaviors. Moreover, Hirshfeld surface and 2D fingerprint analyses revealed significant intermolecular interactions within the crystal structures, predominantly H-H and H-O contacts. Molecular docking studies demonstrate strong binding affinities of the synthesized compounds to the active site of protein 7B2W, suggesting potential therapeutic applications against various isolated smooth muscles and neurotransmitters.
RESUMEN
The title compound, C16H24Br2O, was synthesized from the reaction of ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from Atlas cedar (Cedrus atlantica). The asymmetric unit contains two independent mol-ecules with similar conformations. Each mol-ecule is built up from two fused seven-membered rings and an additional three-membered ring. In both mol-ecules, one of the seven-membered rings has a chair conformation, whereas the other displays a screw-boat conformation.
RESUMEN
The title compound, C16H24Br2O, was synthesized by three steps from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from essential oil of the Atlas cedar cedrus atlantica. The asymmetric unit contains two independent mol-ecules with almost identical conformations. Each mol-ecule is built up from two fused six-membered rings, one having a chair conformation and the other a boat conformation, and an additional three-membered ring arising from the reaction of himachalene with di-bromo-carbene. In the crystal, there are no significant intermolecular interactions present. The absolute structure of the title compound was confirmed by resonance scattering.
RESUMEN
The title compound, C25H33BrN2O4, was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3,14-dioxa-tri-cyclo-[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 an additional ep-oxy ring system and a bromo-phenyl-piperazine 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 hy-droxy group forming the flap. An intra-molecular O-Hâ¯N hydrogen bond stabilizes the mol-ecular conformation. The crystal packing features C-Hâ¯O hydrogen bonds, which link the mol-ecules into zigzag chains running along the b-axis direction.
RESUMEN
The title compound, C25H34N2O5, was synthesized from 9α-hy-droxy-parthenolide (9α-hy-droxy-4,8-dimethyl-12-methylen-3, 14-dioxa-tri-cyclo-[9.3.0.0(2,4)]tetra-dec-7-en-13-one), which in turn was isolated from the chloro-form extract of the aerial parts of Anvillea radiata. The mol-ecule comprises a ten-membered ring fused to a five-membered ring with an additional ep-oxy ring system fused to the ten-membered ring. The five-membered ring also carries a 4-hy-droxy-phenyl-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 hy-droxy 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 0.53â (5):0.47â (5). An intra-molecular O-Hâ¯N hydrogen-bond stabilizes the mol-ecular conformation. In the crystal, C-Hâ¯O hydrogen bonds link the mol-ecules into zigzag chains running along the a-axis direction.
RESUMEN
The title compound, C15H26O2, was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the Atlas cedar (cedrus atlantica). The mol-ecule is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The seven- and six-membered rings each have a twist-boat conformation. In the crystal, O-Hâ¯O hydrogen bonds link the mol-ecules into zigzag chains running along the b-axis direction.
RESUMEN
The title compound, C16H24Br2O was synthesized by three steps from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from essential oil of the Atlas cedar (Cedrus atlantica). The mol-ecule is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The six-membered ring shows a chair conformation. One C atom in the seven-membered ring and two methyl groups attached to the ring are disordered over two sets of sites, with an occupancy ratio of 0.658â (7):0.342â (7).
RESUMEN
The title compound, C(17)H(24)Cl(4), was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings and two three-membered rings from the reaction of ß-himachalene with dichloro-carbene. The six-membered ring shows a chair conformation, whereas the seven-membered ring displays a boat conformation.
RESUMEN
The title compound, C17H26Cl2, was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The asymmetric unit contains two independent mol-ecules with similar conformations. Each mol-ecule is built up from fused six- and seven-membered rings and two three-membered rings from the reaction of ß-himachalene with di-chloro-carbene. In both mol-ecules, the six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. The absolute configuration was established from anomalous dispersion effects.
RESUMEN
The title compound, C17H24Br2Cl2, was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule contains fused six-, seven- and two three-membered rings. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a boat conformation. The absolute structure was unambiguously established from anomalous dispersion effects. The crystal packing exhibits no short inter-molecular contacts.
RESUMEN
The title compound, C17H24Br2Cl2, was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The asymmetric unit contains two independent mol-ecules. Each mol-ecule is built up from fused six-, seven- and two three-membered rings. In both mol-ecules, the six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. No specific inter-molecular inter-actions are noted in the crystal packing.
RESUMEN
The title compound, C16H22Cl2O, was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with di-chloro-carbene. The six-membered ring has an envelope conformation, with the C atom belonging to the three-membered ring forming the flap, whereas the seven-membered ring displays a screw-boat conformation; the dihedral angle between the rings (all atoms) is 59.65â (14)°.
RESUMEN
The title compound, C16H24Cl2O, was synthesized in three steps from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from essential oil of the Atlas cedar (cedrus atlantica). The asymmetric unit contains two independent mol-ecules with similar conformations. Each mol-ecule is built up from two fused seven-membered rings and an additional three-membered ring arising from the reaction of himachalene with di-chloro-carbene. The dihedral angles between the mean planes of the two seven-membered rings are 75.03â (9) and 75.02â (9)° in the two independent mol-ecules.
RESUMEN
The title compound, C17H26Br2, was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The asymmetric unit contains two independent mol-ecules with similar conformations. Each mol-ecule is built up from fused six- and seven-membered rings and two appended three-membered rings. In both mol-ecules, the six-membered ring has a screw boat conformation, whereas the seven-membered ring displays a boat conformation. No specific inter-molecular inter-actions were discerned in the crystal packing.
RESUMEN
The title compound, C16H22Br2Cl2, was synthesized from ß-him-achalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings and an appended three-membered ring. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a chair conformation. The dihedral angle between the two best plane through each ring is 59.5â (2)°. No specific inter-molecular inter-actions were discerned in the crystal packing.
RESUMEN
The title compound, C17H21NO2, was synthesized by the reaction of (1R)-(+)-3-benzyl-camphor and hydroxyl-amine. The oxazole ring makes a dihedral angle of 23.42â (16)° with the phenyl ring. The six-membered ring of the norboryl group adopts a boat conformation, whereas each of the five-membered rings of the norboryl group displays a flattened envelope conformation, with the C atom carrying the methyl groups representing the flap for both rings. In the crystal, mol-ecules are linked into zigzag chains propagating along the b axis by O-Hâ¯N hydrogen bonds.
RESUMEN
The title compound, C16H28O, was synthesized by three steps from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The mol-ecule is built up from fused six- and seven-membered rings and an appended three-membered ring. The six-membered ring has twist-boat conformation, whereas the seven-membered ring displays a chair conformation. In the crystal, mol-ecules are linked into chains propagating along the a-axis direction by O-Hâ¯O hydrogen bonds.
RESUMEN
The title compound, C16H24Br2O, was synthesized from the reaction of ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from Atlas cedar (Cedrus atlantica) essential oil, after reaction with di-bromo-carbene. The asymmetric unit contains two independent mol-ecules with similar conformations. Each mol-ecule is built up from fused six-and seven-membered rings and two three-membered rings. In both mol-ecules, the six-membered ring has an envelope conformation with the flap provided by the C atom of the ep-oxy ring, whereas the seven-membered ring displays a chair conformation. The crystal packing is governed only by van der Waals inter-actions. The absolute configuration was established from anomalous dispersion effects.
RESUMEN
The title compound, C16H24Br2O, was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The mol-ecule contains fused six- and seven-membered rings, each linked to a three-membered ring. The six-membered ring has a half-chair conformation, while the seven-membered ring displays a chair conformation. The dihedral angle between the mean planes through the six- and seven-membered rings is 39.55â (12)°. The two three-membered rings, linked to the six- and seven-membered rings, are nearly perpendicular to the six-membered ring, making dihedral angles of 78.6â (2) and 80.5â (2)°, respectively. The absolute structure was established unambiguously from anomalous dispersion effects. In the crystal, each mol-ecule is linked to its symmetry-equivalent partner by C-Hâ¯O hydrogen bonds, forming zigzag chains parallel to [100].
RESUMEN
The title compound, C16H25Cl2N, was synthesized from ß-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzocyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus Atlantica). The mol-ecule is built up from fused six- and seven-membered rings linked to two three-membered rings. The six-membered ring shows a half-chair conformation, whereas the seven-membered ring displays a boat conformation. The dihedral angle between the mean planes through the six- and seven-membered rings is 59.8â (2)°. The two three-membered rings lie to one side and each is nearly perpendicular to the six-membered ring, forming dihedral angles of 83.2â (2) and 86.0â (2)°. The absolute structure was established unambiguously from anomalous dispersion effects. No specific inter-molecular inter-actions are noted in the crystal structure.