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Crystal structure of (Z)-7,8-di-chloro-4-(2-oxo-propyl-idene)-4,5-di-hydro-1H-1,5-benzodiazepin-2(3H)-one.

ABSTRACT: In the title compound, C12H10Cl2N2O2, the seven-membered heterocycle displays a half-chair conformation. The mean plane through the oxo-propyl-idene group makes a dihedral angle of 36.44 (9)° with the fused benzene ring. An intra-molecular N-H⋯O hydrogen bond to close an S(6) loop is noted. An important feature of the mol-ecular packing are N-H⋯O hydrogen bonds that lead to the formation of helical supra-molecular chains along the b axis.

SUBMITTER: Lahmidi S

PROVIDER: S-EPMC4719978 | biostudies-literature |

REPOSITORIES: biostudies-literature

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(E)-3-[(Di-methyl-amino)-methyl-idene]-4-phenyl-1H-1,5-benzodiazepin-2(3H)-one.

Project description:The asymmetric unit of the title compound, C18H17N3O, consists of two independent mol-ecules, each having an E conformation with respect to the C=C bond between the benzodiazepinone and di-methyl-amine groups. In the crystal, the two independent mol-ecules are linked into a dimer by a pair of N-H⋯O hydrogen bonds.

| S-EPMC3998293 | biostudies-literature

(E)-3-[(Di-methyl-amino)-methyl-idene]-4-phenyl-1-(prop-2-yn-yl)-1H-1,5-benzodiazepin-2(3H)-one.

Project description:The title compound, C21H19N3O, exhibits an E configuration with respect to the C=C bond between the benzodiazepine and tri-methyl-amine groups. The seven-membered diazepine ring displays a boat conformation. In the crystal, mol-ecules are linked by a C-H?O hydrogen bond, forming a chain along [110].

| S-EPMC3914077 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (4<i>Z</i>)-1-butyl-4-(2-oxo-propyl-idene)-2,3,4,5-tetra-hydro-1<i>H</i>-1,5-benzodiazepin-2-one.

Project description:The asymmetric unit of the title compound, C16H20N2O2, consists of two independent mol-ecules differing slightly in the conformations of the seven-membered rings and the butyl substituents, where the benzene rings are oriented at a dihedral angle of 34.56 (3)°. In the crystal, pairwise inter-molecular C-H⋯O and complementary intra-molecular C-H⋯O hydrogen bonds form twisted strips extending parallel to (012). These strips are connected into layers parallel to (111) by additional inter-molecular C-H⋯O hydrogen bonds. The layers are further joined by C-H⋯π inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H⋯H (65.5%), H⋯C/C⋯H (16.0%) and H⋯O/O⋯H (15.8%) inter-actions.

| S-EPMC6218913 | biostudies-literature

5-Acetyl-3-hy-droxy-4-phenyl-4,5-dihydro-1H-1,5-benzodiazepin-2(3H)-one.

Project description:In the title compound, C(17)H(16)N(2)O(3), the seven-membered diazepine ring adopts a boat conformation with the hy-droxy-substituted C atom at the prow and fused benzene ring C atoms at the stern. The phenyl substituent occupies an equatorial position. The amino group of the ring system is a hydrogen-bond donor to the oxo O atom of an inversion-related mol-ecule, and the hy-droxy group is a hydrogen-bond donor to the acetyl O atom of another inversion-related mol-ecule. The two hydrogen bonds generate a ribbon motif parallel to [10[Formula: see text]] in the crystal structure.

| S-EPMC3238984 | biostudies-literature

4-Phenyl-1H-1,5-benzodiazepin-2(3H)-one.

Project description:In the title compound, C15H12N2O, the phenyl ring makes a dihedral angle of 32.45 (9)° with the benzene ring of the 1,5-benzodiazepin-2-one unit. The seven-membered ring adopts a boat conformation with the methyl-ene group as the prow and the fused benzene-ring C atoms as the stern. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R2(2)(8) loops. The dimers are further linked by C-H⋯O hydrogen bonds, so forming a column along the a-axis direction.

| S-EPMC3588955 | biostudies-literature

Carbamo-yl(di-amino-methyl-idene)aza-nium 3-nitro-5-oxo-4,5-di-hydro-1H-1,2,4-triazol-4-ide.

Project description:In the anion of the title salt, C2H7N4O(+)·C2HN4O3 (-), the negative charge resides formally on the N(3) atom of the triazole ring. In the crystal, the N(3) and exocyclic O atoms are hydrogen-bond acceptors with respect to the formally double-bond iminium and amido N atoms of the cation. The cation and anion are almost planar (r.m.s. deviations = 0.012 and 0.051?Å, respectively), but they are slightly bent with respect to each other [dihedral angle = 12.6?(1)°]. In the crystal, adjacent anions and cations are linked by extensive N-H?N and N-H?O hydrogen bonds, generating a ribbon running along the b-axis direction.

| S-EPMC3770364 | biostudies-literature

2-(4-Phenyl-3H-1,5-benzodiazepin-2-yl)phenol.

Project description:In the title compound, C(21)H(16)N(2)O, the dihedral angle between the pendant aromatic rings is 74.2-(1)°.. The conformation is stabilized by an intramolecular O-H⋯N hydrogen bond.

| S-EPMC2960137 | biostudies-literature

1,5-Benzodiazepin-2(3H)-ones: In Vitro Evaluation as Antiparkinsonian Agents.

Project description:A new series of twenty-three 1,5-benzodiazepin-2(3H)-ones were synthesized and evaluated in the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid (ABTS), ferric reducing antioxidant power (FRAP), and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays as a new chemotype with antioxidant and good drug-like properties. All of the derivatives showed low cytotoxicity in comparison to curcumin against the human neuroblastoma SH-SY5Y and the human hepatoma HepG2 cell lines. Experimental solubility in bio-relevant media showed a good relationship with melting points in this series. Five compounds with the best antioxidant properties showed neuroprotectant activity against H2O2-induced oxidative stress in the SH-SY5Y cell line. From them, derivatives 4-phenyl-1H-1,5-benzodiazepin-2(3H)-one (18) and 4-(3,4,5-trimethoxyphenyl)-1H-1,5-benzodiazepin-2(3H)-one (20) yielded good neuroprotection activity in the same neuronal cell line under 6-OHD and MPP+ insults as in vitro models of mitochondrial dysfunction and oxidative stress in Parkinson's disease (PD). Both compounds also demonstrated a significant reduction of intracellular Reactive Oxygen Species (ROS) and superoxide levels, in parallel with a good improvement of the Mitochondrial Membrane Potential (ΔΨm). Compared with curcumin, compound 18 better reduced lipid peroxidation levels, malondialdehyde (MDA), in SH-SY5Y cells under oxidative stress pressure and recovered intracellular glutathione synthetase (GSH) levels. Apoptosis and caspase-3 levels of SH-SY5Y under H2O2 pressure were also reduced after treatment with 18. Neuroprotection in neuron-like differentiated SH-SY5Y cells was also achieved with 18. In summary, this family of 1,5-benzodiazepin-2-ones with an interesting antioxidant and drug-like profile, with low cytotoxic and good neuroprotectant activity, constitutes a new promising chemical class with high potential for the development of new therapeutic agents against PD.

| S-EPMC8533176 | biostudies-literature

Crystal structures of methyl 3-phenyl-4,5-di-hydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl-ate and methyl 1-methyl-3-phenyl-4,5-di-hydro-1H,3H-benzo[4,5]imidazo[2,1-c][1,4]oxazepine-4-carboxyl-ate.

Project description:The title compounds, C19H18N2O3, (I), and C20H20N2O3, (II), differ only by a methyl substituent on the seven-membered oxazepine ring in (II). In both compounds, these rings have a twist-chair conformation. The phenyl ring makes a dihedral angle of 73.42?(10)° with the benzimidazole ring system mean plane (r.m.s. deviation = 0.015?Å) in (I) and 83.07?(7)° in (II) (r.m.s. deviation = 0.026?Å). The methyl carboxyl-ate groups are planar to within 0.031?(2) in (I) and 0.003?(2)?Å in (II). They are inclined to the phenyl and benzimidazole ring system by 33.78?(16) and 87.56?(14)°, respectively, in (I) and by 53.04?(12) and 60.22?(11)°, respectively, in (II). In the crystal of (I), mol-ecules stack in a herringbone fashion and are linked by C-H?O hydrogen bonds, forming chains along [100]. In the crystal of (II), there are no significant inter-molecular inter-actions present.

| S-EPMC4257324 | biostudies-literature

N'-[(4Z)-1-(3-Methyl-5-oxo-1-phenyl-4,5-di-hydro-1H-pyrazol-4-yl-idene)hex-yl]benzene-sulfono-hydrazide.

Project description:In the title compound, C22H26N4O3S, the dihedral angle between the pyrazoloneand phenyl rings is 21.73?(4)°. The benzensulfono-hydrazide group adopts a gauche conformation about the N-N vector. The C-N-N-S torsion angle is -109.88?(13)°. The mol-ecule exists as the enamine tautomeric form (C=C-NH). An intra-molecular N-H?O=C hydrogen bond occurs. In the crystal, mol-ecules are linked by pairs of N-H?O=C hydrogen bonds, forming centrosymmetric dimers.

| S-EPMC4051048 | biostudies-literature

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