Investigation of the Fluorescence Turn-off Mechanism, Genome, Molecular Docking In Silico and In Vitro Studies of 2-Acetyl-3H-benzo[f]chromen-3-one
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ABSTRACT:
SUBMITTER: Koppal V
PROVIDER: S-EPMC9280945 | biostudies-literature |
REPOSITORIES: biostudies-literature
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Project description:The title compound, C15H9FO3, was obtained in a one-pot synthesis by Suzuki-Miyaura cross-coupling and nucleophilic substitution reaction of 4'-chloro-2',5'-di-fluoro-aceto-phenone with o-(meth-oxy-carbon-yl)phenyl-boronic acid. The asymmetric unit contains two crystallographically independent mol-ecules related by a non-crystallographic inversion centre. There are face-to-face stacking inter-actions between the aromatic rings of the benzoate and aceto-phenone units of the symmetry-independent mol-ecules [centroid-centroid distances = 3.870?(3) and 3.986?(3)?Å]. In the crystal, mol-ecules are further assembled via stacking inter-actions along the a-axis direction. One of the mol-ecules inter-acts with its inversion equivalent [centroid-centroid distance between the aromatic rings of the benzoate and aceto-phenone units = 3.932?(3)?Å], and the other inter-acts with its twofold axis equivalent [centroid-centroid distance between the aromatic rings of aceto-phenone units = 3.634?(3)?Å].
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Project description:In the title compound, C(9)H(8)O(2), a benzo-annulated heterocyclic ketone, the non-aromatic six-membered ring adopts an E(2) conformation. In the crystal, C-H?O contacts connect the mol-ecules into double sheets perpendicular to the crystallographic a axis. The centroid-centroid distance for two ?-systems is 3.7699?(6)?Å.
| S-EPMC3089272 | biostudies-literature
Project description:BackgroundThe persistent appearance of viral strains that causes a resistant viral infection has led to continuous trials for the design and development of novel antiviral compounds. Benzoquinazoline compounds have been reported to exhibit an interesting antiviral activity. This work aims to study and evaluate the antiviral activity of a newly prepared 2-thioxo-benzo[g]quinazolin-4(3H)-one series against herpes simplex (HSV-1 & 2) and coxsackievirus (CVB4).MethodsThe antiviral activity was performed using the MTT assay, in which Vero cells (obtained from the American Type Culture Collection, ATCC) were propagated in fresh Dulbecco's Modified Eagle's Medium (DMEM) and challenged with 10(4) doses of the virus. Thereafter, the cultures were treated simultaneously with two-fold serial dilutions of the tested compound and incubated at 37 °C for 48 h. Molecular docking studies were done on the CVB4 2A proteinase enzyme using Molegro Virtual Docker software.ResultsThe cytotoxicity (CC50), effective concentration (EC50) and the selectivity index (SI) values were determined. Based on their EC50 values, a number of the investigated compounds demonstrated weak to moderate activity relative to their parents. Accordingly, compounds 5-9, 11, 15-18, 21, 22, 24, 25, 27 and 28 were active against CVB4, and compounds 5 and 24 were active against HSV-1 and 2 in comparison to ribavirin and acyclovir, which were used as reference drugs.ConclusionThe obtained results gave us some useful insights about the characteristic requirements for future trials to build up and design more active and selective antiviral 2-thioxo-benzo[g]quinazolin-4(3H)-one agents.Graphical abstractCompound 24 superimposed with Ribavirin in CV B4 2A Proteinase enzyme (PDB: 1Z8R) active site.
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Project description:In the crystal structure of the title compound, C(15)H(11)FO(2), mol-ecules form inversion dimers through pairs of weak C-H⋯O hydrogen bonds. Dimers oriented in parallel, linked by C-H⋯π contacts, are arranged in columns along the b axis. The fluoro-phenyl ring and the benzene ring of the 2H-chromen-4(3H)-one unit are inclined to one another by 70.41 (16)°. They are respectively parallel in a given column or almost perpendicular [oriented at an angle of 87.8 (1)°] in neighbouring (inversely oriented) columns, forming a herringbone pattern.
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Project description:In the title compound, C(20)H(19)N O(2)S(2),the 3Hbenzo-chromene ring system is nearly planar, with a maximum deviation of 0.036?(2)?Å, and the piperidine ring adopts a chair conformation: the bond-angle sum for its N atom is 358.7°. The dihedral angle between the 3H-benzo[f]chromene ring and the piperidine ring is 89.07?(8)°. In the crystal, C-H?O hydrogen bonds lead to [010] C(6) chains and weak aromatic ?-? inter-actions between the fused pyran ring and fused benzene ring of benzochromene [centroid-centroid distance = 3.652?(1)?Å] are also observed.
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Project description:In the title compound, C11H8O3, the fused-ring system is almost planar (r.m.s. deviation = 0.020 Å), with the largest deviation from the least-squares plane [0.0462 (17) Å] being for a pyran C atom. The dihedral angle between the plane of the fused-ring system and acetyl plane is 5.149 (16)°. In the crystal, the fused rings are linked by aromatic π-π stacking inter-actions [centroid-centroid distance between the benzene and pyran rings = 3.643 (6) Å] and C-H⋯O hydrogen bonds, generating a three-dimensional network.
| S-EPMC4518922 | biostudies-literature
Project description:In the title compound, C(17)H(15)NO(2)S(2), the 3H-benzo[f]chromene ring system is distinctly twisted; the dihedral angle between the pyran ring and its opposite benzene ring is 9.11?(8)°. The N,N-dimethyl-carbamodithio-ate residue lies almost perpendicular to the pyran ring [dihedral angle = 85.15?(7)°]. In the crystal, weak C-H?O hydrogen bonds link the mol-ecules into C(10) chains propagating in [001].
| S-EPMC3470360 | biostudies-literature
Project description:In the title compound, C(19)H(30)N(2)O, the fused ring system is essentially planar, the maximum deviation from the mean plane being 0.013?(2)?Å for the N atom bearing the dodecyl chain. The 1-dodecyl group is almost perpendicular to the 1H-benzo[d]imidazol-2(3H)-one plane as indicated by the dihedral angle of 82.9?(2)°between planes through the fused ring system and the first three C atoms of the chain. The C-C-C-C torsion angles (about ±179°) of the dodecyl group indicate an anti-periplanar conformation. In the crystal, inversion dimers are formed by pairs of N-H?O hydrogen bonds.
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Project description:In the title coumarin derivative, C(13)H(12)O(4), the 2H-chromene ring system is essentially planar [maximum deviation = 0.047?(1)?Å]. An intra-molecular hydrogen bond is observed between the hy-droxy and the ketonic O atoms. In the crystal, pairs of inter-molecular C-H?O hydrogen bonds link inversion-related mol-ecules into dimers. Additional inter-molecular C-H?O hydrogen bonds further inter-connect these dimers into two-dimensional arrays incorporating R(2) (2)(9) ring motifs.
| S-EPMC3011552 | biostudies-literature
Project description:In the mol-ecule of the title compound, C(14)H(9)Cl(2)NO(2), the essentially planar phthalide group is oriented at a dihedral angle of 63.23?(5)° with respect to the substituted aromatic ring. In the crystal structure, inter-molecular C-H?O and N-H?O hydrogen bonds link the mol-ecules, generating R(4) (4)(21) ring motifs to form a three-dimensional network.
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