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Ethyl 23-benzyl-8,11,14-trioxa-23,28,29-triaza-penta-cyclo-[19.7.1.0(2,7).0(15,20).0(22,27)]nona-cosa-2,4,6,15(20),16,18,21,26-octa-ene-26-carboxyl-ate.

ABSTRACT: The title compound, C33H35N3O5, is the product of the multicomponent condensation of 1-benzyl-4-eth-oxy-carbonyl-piperidin-3-one with 1,5-bis-(2-formyl-phen-oxy)-3-oxapentane and ammonium acetate. The mol-ecule comprises a penta-cyclic system containing the aza-14-crown-4-ether macrocycle, tetra-hydro-pyrimidine, tetra-hydro-pyridine and two benzene rings. The aza-14-crown-4-ether ring adopts a bowl conformation with a dihedral angle of 62.37?(5)° between the benzene rings. The tetra-hydro-pyrimidine ring has an envelope conformation with the chiral C atom as the flap, whereas the tetra-hydro-pyridine ring adopts a distorted chair conformation. Two amino groups are involved in intra-molecular N-H?O hydrogen bonds. In the crystal, weak C-H?O hydrogen bonds link the mol-ecules into layers parallel to the ab plane.

SUBMITTER: Hieu TH

PROVIDER: S-EPMC3629615 | BioStudies | 2013-01-01T00:00:00Z

REPOSITORIES: biostudies

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24-Acetyl-8,11,14-trioxa-24,27-diaza-penta-cyclo-[19.5.1.1(22,26).0(2,7).0(15,20)]octa-cosa-2,4,6,15(20),16,18-hexaen-28-one.

Project description:The title compound, C(25)H(28)N(2)O(5), is a product of the Petrenko-Kritchenko condensation of N-acetyl-piperidone with 1,5-bis-(2-formyl-phen-oxy)-3-oxapentane and ammonium acetate. The mol-ecule comprises a fused penta-cyclic system containing an aza-14-crown-3-ether macrocycle, two piperidone and two benzene rings. The aza-14-crown-3-ether ring adopts a bowl conformation. The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether unit is 70.18?(4)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The conformation of the central piperidone ring is determined by two intra-molecular N-H?O hydrogen bonds. In the crystal, mol-ecules are linked by weak C-H?O inter-actions into chains along [010].

1000-01-01 | S-EPMC3393972 | BioStudies

One-pot synthesis of (1RS,21SR)-diethyl 2-[23-amino-22-eth-oxy-carbonyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.02,7.015,20]penta-cosa-2,4,6,15(20),16,18,22-heptaen-25-yl]but-2-endioate.

Project description:The title compound, C30H34N2O9 (4), is a product of the Michael reaction of aza-crown ether with dimethyl acetyl-enedi-carboxyl-ate modified by an addition of NH3 (aq.) at 298?K. The aza-14-crown-4-ether ring adopts a bowl conformation. The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 8.65?(5)°. The tetra-hydro-pyridine ring has a boat conformation. The mol-ecular conformation is supported by one N-H?O and two C-H?O intra-molecular hydrogen bonds. Both heterocyclic and amino N atoms have essentially planar configurations (sums of the bond angles are 359.35 and 358.00°). Compound 4 crystallizes as a racemate consisting of enanti-omeric pairs of the 1R,21S diastereomer. In the crystal, mol-ecules of 4 are connected by N-H?O hydrogen bonds, forming chains along [100]. According to the PASS program (computer prediction of biological activities), compound 4 may exhibit anti-allergic (72% probability) and anti-asthmatic (67%) activity, as well as be a membrane permeability inhibitor (65%).

1000-01-01 | S-EPMC6127715 | BioStudies

Crystal structure of (1RS,21SR,22RS,24SR)-28-oxo-24-propyl-8,11,14-trioxa-24,27-di-aza-penta-cyclo[19.5.1.1(22,26).0(2,7).0(15,20)]octa-cosa-2,4,6,15(20),16,18-hexa-ene acetic acid monosolvate.

Project description:The title compound, C26H32N2O4(M)·C2H4O2, (I), is the product of the Petrenko-Kritchenko condensation of N-propyl-piperidinone with 1,5-bis-(2-formyl-phen-oxy)-3-oxa-pentane and ammonium acetate. In M, the aza-14-crown-3-ether ring adopts a bowl conformation, with the configuration of the C-O-C-C -O-C-C-O-C polyether chain being t-g ((-))-t-t-g ((+))-t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the planes of the benzene rings fused to the aza-14-crown-4-ether moiety is 62.75?(5)°. The central piperidinone ring has a boat conformation, whereas the terminal piperidinone ring adopts a chair conformation. The boat conformation of the central piperidinone ring is supported by the bifurcated intra-molecular N-H?O hydrogen bond. In the crystal, each solvent mol-ecule is linked to mol-ecule M via strong O-H?N hydrogen bonding, forming hydrogen-bonded pairs of mol-ecules, which further inter-act through weak C-H?O hydrogen bonds, forming layers parallel to the ac plane.

1000-01-01 | S-EPMC4908554 | BioStudies

Dimethyl 2-[24-acetyl-28-oxo-8,11,14-trioxa-24,27-diaza-penta-cyclo-[19.5.1.1(22,26).0(2,7).0(15,20)]octa-cosa-2,4,6,15(20),16,18-hexaen-27-yl]but-2-enedioate.

Project description:The title compound, C(31)H(34)N(2)O(9), is a product of the Michael addition of the cyclic secondary amine subunit of the (bis-pidino)aza-14-crown-4 ether to dimethyl acetyl-ene-dicarboxyl-ate. The mol-ecule comprises a tricyclic system containing the aza-14-crown-3 ether macrocycle and two six-membered piperidinone rings. The aza-14-crown-3-ether ring adopts a bowl conformation with a dihedral angle between the planes of the fused benzene rings of 51.14?(5)°. The central piperidone ring has a boat conformation, whereas the terminal piperidone ring adopts a chair conformation. The dimethyl ethyl-enedicarboxyl-ate fragment has a cis configuration with a dihedral angle of 56.56?(7)° between the two carboxyl-ate groups. The crystal packing is stabilized by weak C-H?O hydrogen bonds.

1000-01-01 | S-EPMC3414347 | BioStudies

Crystal structure of 22,24,25-trimethyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.02,7.015,20]penta-cosa-2,4,6,15(20),16,18-hexaen-23-one.

Project description:The title compound, C24H29NO4, is the product of a Petrenko-Kritchenko condensation of 1,5-bis-(2-formyl-phen-oxy)-3-oxa-pentane, pentan-3-one and methyl-ammonium acetate in ethanol. The mol-ecule has mirror symmetry. The aza-14-crown-3 ether ring adopts a bowl conformation stabilized by a weak intra-molecular C-H?O hydrogen bond. The conformation of the C-O-C-C-O-C-C-O-C polyether chain is t-g+-t-t-g--t (t = trans, 180°; g = gauche, ±60°). The dihedral angle between the benzene rings fused to the aza-14-crown-4-ether moiety is 72.68?(4)°. The piperidinone ring adopts a chair conformation. The nitro-gen atom has a trigonal-pyramidal geometry, the sum of the bond angles being 335.9°. In the crystal, the mol-ecules are linked by weak C-H?O inter-actions, forming zigzag chains propagating along the [100] direction.

1000-01-01 | S-EPMC5290547 | BioStudies

meso-(1S*,21R*)-25-Methyl-8,11,14-trioxa-22,24,25-triaza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexa-ene-23-thione chloro-form monosolvate.

Project description:The title compound crystallizes as a chloro-form solvate, C(20)H(23)N(3)O(3)S·CHCl(3), with two crystallographically independent units. The independent units have distinctly different inter-action patterns between the aza-crown macrocycle and the chloro-form solvent mol-ecule. In one of them, the chloro-form mol-ecule forms C-H?N and Cl?H-C hydrogen bonds with the aza-crown macrocycle (as a proton donor and an acceptor, respectively), whereas in the other, one of the chloro-form mol-ecules is bound to the aza-crown macrocycle by an attractive Cl?O [3.080?(3)?Å] inter-action. The aza-crown macrocycles of different units are structurally similar; the aza-14-crown-3-ether ring adopts a bowl conformation with dihedral angles between the planes of the fused benzene rings of 60.7?(1) and 68.0?(1)°. The triazinane-thione ring in both cases has a sofa conformation. The crystal packing is characterized by N-H?S, N-H?O, C-H?Cl and C-H?S hydrogen bonds.

2012-01-01 | S-EPMC3470208 | BioStudies

(1'S,12'R,13'S,17'S)-15',15'-Dimethyl-1,2-dihydro-11',14',16',18'-tetra-oxa-7'-aza-spiro-[indole-3,8'-penta-cyclo-[10.6.0.0(2,9).0(3,7).0(13,17)]octa-deca-ne]-2,10'-dione.

Project description:In the title compound, C22H24N2O6, the indole ring has a twist conformation and the tetra-hydro-2H-pyran-2-one ring a half-chair conformation. One of the pyrrolidine rings adopts an envelope conformation on the N atom, while the other has a twist conformation; the 'butterfly' angle between their mean planes is 62.98?(11)°. The dioxolane ring adopts a twist conformation and the tetra-hydro-furan ring has an envelope conformation on the C atom in the fused tetra-hydro-2H-pyran-2-one ring adjacent to the O atom of the tetra-hydro-furan ring. The 'butterfly' angle between the mean planes of these two five-membered rings is 69.14?(10)°. In the crystal, mol-ecules are linked by N-H?O hydrogen bonds, forming chains along the a axis.

1000-01-01 | S-EPMC3629507 | BioStudies

Ethyl 4-(4-chloro-phen-yl)-6-methyl-2-thioxo-1,2,3,4-tetra-hydro-pyrimidine-5-carboxyl-ate.

Project description:In the title compound, C(14)H(15)ClN(2)O(2)S, the tetra-hydro-pyrimidine ring adopts a twisted boat conformation with the carbonyl group in an s-trans conformation with respect to the C=C double bond of the six-membered tetra-hydro-pyrimidine ring. The mol-ecular conformation is determined by an intra-molecular C-H?? inter-action. The crystal structure is further stabilized by inter-molecular N-H?O mol-ecular chains and centrosymmetric N-H?S dimers.

2009-01-01 | S-EPMC2970428 | BioStudies

(1R*,21S*,22R*,24S*)-Methyl ethyl 2-[23-hy-droxy-22,24-diphenyl-8,11,14-trioxa-25-aza-tetra-cyclo-[19.3.1.0(2,7).0(15,20)]penta-cosa-2,4,6,15(20),16,18-hexaen-25-yl]but-2-enedioate.

Project description:The title compound, C40H41NO8, is a product of the reduction of the cyclic carbonyl group of the ?-piperidone subunit of the aza-14-crown-4 ether with subsequent re-esterification of its dimethyl butenoate substituent into a monoethyl monomethyl group. The aza-crown macrocycle exhibits a bowl conformation with a dihedral angle of 70.82?(5)° between the benzene rings fused to it. The piperidine ring adopts a chair conformation and the methyl ethyl ethyl-enedi-carboxyl-ate fragment has a cis conformation, with a dihedral angle of 66.51?(7)° between the two carboxyl-ate groups. The ethyl group is disordered over two sites with occupancies of 0.70?(1):0.30?(1). In the crystal, mol-ecules form inversion dimers, via pairs of O-H?O hydrogen bonds, that stack along the a axis.

1000-01-01 | S-EPMC3772461 | BioStudies

Crystal structure of 26-(4-methyl-phen-yl)-8,11,14,17-tetra-oxa-28-aza-tetra-cyclo[22.3.1.0(2,7).0(18,23)]hexa-cosa-2,4,6,18(23),19,21,24(1),25,27-nona-ene.

Project description:The title compound, C30H29NO4, is a tetra-cyclic system containing a 4-aryl-pyridine fragment, two benzene rings and an aza-17-crown-5 ether moiety, in a bowl-like arrangement. The pyridine ring is inclined to the 4-methyl-phenyl ring by 26.64?(6)°, and by 57.43?(6) and 56.81?(6)° to the benzene rings. The benzene rings are inclined to one another by 88.32?(6)°. In the crystal, mol-ecules are linked by pairs of C-H?N hydrogen bonds, forming inversion dimers with an R 2 (2)(14) ring motif. The dimers are linked via a number of C-H?? inter-actions, forming a three-dimensional architecture.

1000-01-01 | S-EPMC4908512 | BioStudies

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