16 research outputs found
Synthesis, Structural And Antioxidant Studies Of Some Novel Benzofuran And Phthalimide Derivatives
In this project, two series of heterocyclic analogues bearing a benzofuran (1a-
1q) and a phthalimide (2a-2g) moieties were synthesized and crystallized. All crystal
structures were revealed by single crystal X-ray crystallography technique, supported
by FT-IR and NMR spectral analysis. The molecular structures and interactions of
these compounds were studied and analysed. Besides, the antioxidant potential of all
compounds were evaluated using different antioxidant assays. In the benzofuran
series, eight of seventeen compounds are assembled in a triclini
Crystal structure and Hirshfeld surface analysis of (2E,20E)-3,30-(1,4-phenylene)bis[1-(2,4-difluorophenyl) prop-2-en-1-one]
The asymmetric unit of the title compound, C24H14F4O2, comprises of one and a
half molecules; the half-molecule is completed by crystallographic inversion
symmetry. In the crystal, molecules are linked into a three-dimensional network
by C—H� � �F and C—H� � �O hydrogen bonds. Some of the C—H� � �F links are
unusually short (< 2.20 A ° ). Hirshfeld surface analyses (dnorm surfaces and twodimensional
fingerprint plots) for the title compound are presented and
discussed
Two closely related 2-(benzofuran-2-yl)-2-oxoethyl benzoates: structural differences and C 14H...O hydrogen-bonded supramolecular assemblies
The compounds 2-(1-benzofuran-2-yl)-2-oxoethyl 2-nitrobenzoate, C17H11NO6 (I), and 2-(1-benzofuran-2-yl)-2-oxoethyl 2-aminobenzoate, C17H13NO4 (II),
were synthesized under mild conditions. Their molecular structures were
characterized by both spectroscopic and single-crystal X-ray diffraction analysis.
The molecular conformations of both title compounds are generally similar.
However, different ortho-substituted moieties at the phenyl ring of the two
compounds cause deviations in the torsion angles between the carbonyl group
and the attached phenyl ring. In compound (I), the ortho-nitrophenyl ring is
twisted away from the adjacent carbonyl group whereas in compound (II), the
ortho-aminophenyl ring is almost co-planar with the carbonyl group. In the
crystal of compound (I), two C 14
Three closely related (2E,200E)-3,300-(1,4-phenylene)- bis[1-(methoxyphenyl)prop-2-en-1-ones]: supramolecular assemblies in one dimension mediated by hydrogen bonding and C—Hp interactions
In the title compounds, (2E,20E)-3,30-(1,4-phenylene)bis[1-(2-methoxyphenyl)-
prop-2-en-1-one], C26H22O4 (I), (2E,20E)-3,30-(1,4-phenylene)bis[1-(3-methoxyphenyl)
prop-2-en-1-one], C26H22O4 (II) and (2E,20E)-3,30-(1,4-phenylene)bis[1-
(3,4-dimethoxyphenyl)prop-2-en-1-one], C28H26O6 (III), the asymmetric unit
consists of a half-molecule, completed by crystallographic inversion symmetry.
The dihedral angles between the central and terminal benzene rings are
56.98 (8), 7.74 (7) and 7.73 (7) for (I), (II) and (III), respectively. In the crystal
of (I), molecules are linked by pairs of C—H interactions into chains
running parallel to [101]. The packing for (II) and (III), features inversion
dimers linked by pairs of C—HO hydrogen bonds, forming R2
2(16) and R2
2(14)
ring motifs, respectively, as parts of [201] and [101] chains, respectively
Benzofuranyl Esters: Synthesis, Crystal Structure Determination, Antimicrobial and Antioxidant Activities
A series of five new 2‐(1‐benzofuran‐2‐yl)‐2‐oxoethyl 4-(un/substituted)benzoates
4(a–e), with the general formula of C8H5O(C=O)CH2O(C=O)C6H4X, X = H, Cl, CH3, OCH3
or NO2, was synthesized in high purity and good yield under mild conditions. The synthesized
products 4(a–e) were characterized by FTIR, 1H-, 13C- and 1H-13C HMQC NMR spectroscopic
analysis and their 3D structures were confirmed by single-crystal X-ray diffraction studies.
These compounds were screened for their antimicrobial and antioxidant activities. The
tested compounds showed antimicrobial ability in the order of 4b < 4a < 4c < 4d < 4e and
the highest potency with minimum inhibition concentration (MIC) value of 125 μg/mL was
observed for 4e. The results of antioxidant activities revealed the highest activity for
compound 4e (32.62% ± 1.34%) in diphenyl-2-picrylhydrazyl (DPPH) radical scavenging,
4d (31.01% ± 4.35%) in ferric reducing antioxidant power (FRAP) assay and 4a (27.11% ±
1.06%) in metal chelating (MC) activity
Crystal structure and Hirshfeld surface analysis of (2E,2′E)-3,3′-(1,4-phenylene)bis[1-(2,4-difluorophenyl)prop-2-en-1-one]
The asymmetric unit of the title compound, C24H14F4O2, comprises of one and a half molecules; the half-molecule is completed by crystallographic inversion symmetry. In the crystal, molecules are linked into a three-dimensional network by C—H...F and C—H...O hydrogen bonds. Some of the C—H...F links are unusually short (< 2.20 Å). Hirshfeld surface analyses (dnorm surfaces and two-dimensional fingerprint plots) for the title compound are presented and discussed
Radical scavenging potency of 2-(benzofuran-2-yl)-2-oxoethyl 3-(methyl/amino)benzoate: synthesis, crystal structure and Hirshfeld surface analysis
Two novel 2-(benzofuran-2-yl)-2-oxoethyl 3-(methyl/amino)benzoates 2(a–b), were synthesized under mild conditions and characterized by spectroscopic analysis. The three-dimensional (3D) crystal structures of these compounds were further determined using single crystal X-ray diffraction technique and revealed that both compounds tend to twist away with respect to their attached carbonyl groups at the C(=O)–C–O–C(=O) connecting bridge, exhibiting a nearly perpendicular conformation with torsion angle in a range of 75–94°. In both compounds, each of the benzofuran and substituted phenyl rings are individually planar while almost perpendicular to each other. Their molecular conformation are comparable with related structures from the Cambridge Structural Database (CSD). Furthermore, the intermolecular interactions in these crystal structures were quantified and analyzed using Hirshfeld surfaces computational method. The quantitative data on the percentage contributions of overall interactions on the molecules 2a and 2b (A & B) is calculated by the 2-D fingerprint plots from the HS analysis. These structures were evaluated for their antioxidant properties by diphenyl-2-picrylhydrazyl (DPPH) radical scavenging, ferrous ion chelating (FIC) and hydrogen peroxide radical scavenging assays (H2O2). Noteworthy, compound 2b with an amino substituent attached to the phenyl ring exhibited an IC50 value of 45.37 μg/mL in H2O2 scavenging assay, which showed better scavenging effect than the standard drug, ascorbic acid (IC50=81.02 μg/mL)
Two closely related 2-(benzofuran-2-yl)-2-oxoethyl benzoates: structural differences and C—H...O hydrogen-bonded supramolecular assemblies
The compounds 2-(1-benzofuran-2-yl)-2-oxoethyl 2-nitrobenzoate, C17H11NO6 (I), and 2-(1-benzofuran-2-yl)-2-oxoethyl 2-aminobenzoate, C17H13NO4 (II), were synthesized under mild conditions. Their molecular structures were characterized by both spectroscopic and single-crystal X-ray diffraction analysis. The molecular conformations of both title compounds are generally similar. However, different ortho-substituted moieties at the phenyl ring of the two compounds cause deviations in the torsion angles between the carbonyl group and the attached phenyl ring. In compound (I), the ortho-nitrophenyl ring is twisted away from the adjacent carbonyl group whereas in compound (II), the ortho-aminophenyl ring is almost co-planar with the carbonyl group. In the crystal of compound (I), two C—H...O hydrogen bonds link the molecules into chains propagating along the c-axis direction and the chains are interdigitated, forming sheets parallel to [20-1]. Conversely, pairs of N—H...O hydrogen bonds in compound (II) link inversion-related molecules into dimers, which are further extended by C—H...O hydrogen bonds into dimer chains. These chains are interconnected by π–π interactions involving the furan rings, forming sheets parallel to the ac plane
Three closely related (2E,2′E)-3,3′-(1,4-phenylene)bis[1-(methoxyphenyl)prop-2-en-1-ones]: supramolecular assemblies in one dimension mediated by hydrogen bonding and C—H...π interactions
In the title compounds, (2E,2′E)-3,3′-(1,4-phenylene)bis[1-(2-methoxyphenyl)prop-2-en-1-one], C26H22O4 (I), (2E,2′E)-3,3′-(1,4-phenylene)bis[1-(3-methoxyphenyl)prop-2-en-1-one], C26H22O4 (II) and (2E,2′E)-3,3′-(1,4-phenylene)bis[1-(3,4-dimethoxyphenyl)prop-2-en-1-one], C28H26O6 (III), the asymmetric unit consists of a half-molecule, completed by crystallographic inversion symmetry. The dihedral angles between the central and terminal benzene rings are 56.98 (8), 7.74 (7) and 7.73 (7)° for (I), (II) and (III), respectively. In the crystal of (I), molecules are linked by pairs of C—H...π interactions into chains running parallel to [101]. The packing for (II) and (III), features inversion dimers linked by pairs of C—H...O hydrogen bonds, forming R22(16) and R22(14) ring motifs, respectively, as parts of [201] and [101] chains, respectively