Methoxyphenyl Ring Research Articles

Spectroscopic, Docking and MD Simulation Analysis of an Adamantane Derivative with Solvation Effects in Different Solvents

3-(Adamantan-1-yl)-4-(4-fluorophenyl)-1-{[4-(2-methyoxyphenyl)piprazin-1yl]-methyl}-4,5-dihydro-1H-1,2,4-triazole-5-thione (AFT) was synthesized and spectroscopic investigations have been made experimentally and theoretically. The electrostatic potential maps and frontier orbital visualizations were used to comment of molecular polarity and stability in AFT. In AFT, thione group, methoxyphenyl ring, and triazole are the strongest repulsion and attractive reactive sites. The chemical descriptors in different solvents and NLO properties are predicted. For different solvents and gas phase, UV-vis theoretical spectra are being used to assess the electronic transition. Solvation free energy in water (hydration free energy) indicates good solubility of AFT in an aqueous medium, factor that corroborates the biological activity, in as much as that bioorganic processes occur in aqueous medium. Solvation produces a lowering of absorption in the UV-vis region. After evaluating the drug likeness properties, the title compound was examined for its analgesic activity by means of molecular docking and MD simulations. The MD simulations and docking studies suggested inhibitory activity against analgesic protein glutamate receptor.

Synthesis, structural, spectroscopic, intermolecular interactions, kinetic stability, charge transfer method with DNA bases and electronic properties of (E)-3-(2-ethoxyphenyl)-5-(3-(2-methoxyphenyl)-4methylthiazol-2(3H)-ylidene)-2-thioxothiazolidin-4-one: Computational and experimental approach

In the current paper, the new molecule (E)-3-(2-Ethoxyphenyl) -5-(3-(2methoxyphenyl) -4 methylthiazol-2(3H) -ylidene) -2-thioxothiazolidin-4-one (EMTh2) was synthesized and characterized using FT-IR, UV-vis, NMR, and X-ray diffraction experimental techniques. The experimental structure was determined from single-crystal X-ray diffraction data at low temperature (173 K). The compound crystallizes in the monoclinic system and space group P21/c with cell parameters: a=11.1100(5) Å, b=13.0597(6) Å, c=15.2343(7) Å, β=103.480(5)°, Z=4. R= 0.0512 was the final value for 4372 observed reflections. The two thiazol rings are coplanar, while the ethoxyphenyl and methoxy phenyl rings are essentially perpendicular to these rings with dihedral angle values of 107.2° for C4-N2-C8-C13 and 101.7° for C3-1-C15-C20. All theoretical calculations are performed using DFT with B3LYP functional and 6-31G(d,p) basis set. Both theoretical and experimental molecular structures were investigated and compared to one another. Furthermore, Hirshfeld surface analysis was performed to display surface contours and 2D-fingerprint plots were used to obtain contributions of the most important intermolecular interactions. The theoretical UV-vis spectrum was computed in chloroform as a solvent using the TD-DFT method. 1H and 13C-NMR chemical shifts were calculated using the GIAO approximation and the results were compared to the experimental ones. In addition, natural bond orbital (NBO), global reactivity parameters, MPA and NPA atomic charges, molecular electrostatic potential, Fukui functions were estimated using the same level of theory. The interactions between the investigated molecule and DNA bases (mainly adenine, cytosine, guanine, and thymine) were explored using the electrophilicity-based charge transfer method.

Crystal structure analysis of ethyl 6-(4-meth-oxy-phen-yl)-1-methyl-4-methyl-sulfanyl-3-phenyl-1H-pyrazolo-[3,4-b]pyridine-5-carboxyl-ate.

In the title compound, C24H23N3O3S, the dihedral angle between the fused pyrazole and pyridine rings is 1.76 (7)°. The benzene and meth-oxy phenyl rings make dihedral angles of 44.8 (5) and 63.86 (5)°, respectively, with the pyrazolo-[3,4-b] pyridine moiety. An intra-molecular short S⋯O contact [3.215 (2) Å] is observed. The crystal packing features C-H⋯π inter-actions.

Crystal structure and Hirshfeld surface analysis of 3,5-bis(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

The crystal and molecular structure of a pyrazole derivative (3,5-bis(4-methoxyphenyl)-4,5,dihydro-1H-pyrazole-1-carbothioamide) is determined by the single crystal X-ray diffraction analysis at 296 K. In the title compound C18H19N3O2S (a pyrazoline derivative), the pyrazoline ring adopts an envelope conformation with the C2 atom bonded to the methoxyphenyl ring as the flap atom. The structure displays C—H…S, N—H…O intermolecular hydrogen bonding. The structure also exhibits intramolecular hydrogen bonds of N—H…N and C—H…N types which contribute to the crystal packing and a weak C—H…π interaction. Further, the Hirshfeld surface analysis reveals the nature of intermolecular contacts. The importance of molecular interactions is established from dnorm, shape index, and fingerprint plot, which provides information about the percentage contribution of individual intermolecular contacts to the surface.

Crystal Structure and Hirshfeld Surface Analysis of 3,5-Bis(4-Methoxyphenyl)-4,5-Dihydro-1H-Pyrazole-1-Carbothioamide

The crystal and molecular structure of a pyrazole derivative (3,5-bis(4-methoxyphenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide) is determined by the single crystal X-ray diffraction analysis at 296 K. In the title compound C18H19N3O2S (a pyrazoline derivative), the pyrazoline ring adopts an envelope conformation with the C2 atom bonded to the methoxyphenyl ring as the flap atom. The structure displays C-H…S, N-H…O intermolecular hydrogen bonding. The structure also exhibits intramolecular hydrogen bonds of N-H…N and C-H…N types which contribute to the crystal packing and a weak C-H…π interaction. Further, the Hirshfeld surface analysis reveals the nature of intermolecular contacts. The importance of molecular interactions is established from dnorm, shape index, and fingerprint plot, which provides information about the percentage contribution of individual intermolecular contacts to the surface.

Synthesis, molecular modelling and anticancer evaluation of new pyrrolo[1,2-b]pyridazine and pyrrolo[2,1-a]phthalazine derivatives

Two new series of heterocyclic derivatives with potential anticancer activity, in which a pyrrolo[1,2-b]pyridazine or a pyrrolo[2,1-a]phthalazine moiety was introduced in place of the 3′-hydroxy-4′-methoxyphenyl ring of phenstatin have been synthesised and their structure-activity relationship (SAR) was studied. Fourteen of the new compounds were evaluated for their in vitro cytotoxic activity by National Cancer Institute (NCI) against 60 human tumour cell lines panel. The best five compounds in terms of in vitro growth inhibition were screened in the second stage five dose-response studies, three of them showing a very good antiproliferative activity with GI50<100 nM on several cell lines including colon, ovarian, renal, prostate, brain and breast cancer, melanoma and leukemia. Docking experiments on the biologically active compounds showed a good compatibility with the colchicine binding site of tubulin.

Crystal structures of 3-meth-oxy-4-{[5-(4-meth-oxy-phen-yl)-1,3,4-oxa-diazol-2-yl]meth-oxy}benzo-nitrile and N-(4-{[5-(4-chloro-phen-yl)-1,3,4-oxa-diazol-2-yl]meth-oxy}phen-yl)acetamide.

The title compounds, C18H15N3O4 and C17H14ClN3O3, are heterocyclic 1,3,4-oxa-diazole derivatives which differ from each other in the groups attached to the carbon atoms: a meth-oxy-phenyl ring and a benzo-nitrile group in (I) and a chloro-phenyl ring and an acetamide group in (II). Short intra-molecular C-H⋯O hydrogen bonds occur in both mol-ecules. The crystal structure of (I) features C-H⋯N hydrogen bonds, while in the crystal structure of (II), N-H⋯N, C-H⋯N and C-H⋯O hydrogen bonds are observed.

The Crystal Structure of N-[(2E)-3-(4-Chlorophenyl)prop-2-en-1-yl]-4-methoxy-N-methylbenzenesulfonamide

The title compound C17H18ClNO3S crystallizes in the monoclinic P21/c space group with unit cell parameters a = 15.040 (3) A, b = 9.151 (6) A, c = 13.868 (7) A, β = 116.38 (5)°. Chlorophenyl and methoxyphenyl ring planes are approximately perpendicular and the two moieties form an angle of 82.2°. The crystal packing is stabilized by π–π and Cl–π interactions, which occur between parallel methoxyphenyl and chlorophenyl moieties. Dipolar intermolecular contacts, mainly involving the oxygen atoms and C–H, also contribute to the crystal network. The title compound is formed in the synthetic route for the production of potent inhibitors of calmodulin. Its crystal structure shows the chlorophenyl and methoxyphenyl moieties forming an angle of 82.2°. The crystal packing is stabilized by π–π, Cl–π and dipolar intermolecular contacts.

(3E)-3-[(2E)-3-(4-Methoxyphenyl)prop-2-enylidene]-2,3-dihydro-4H-chromen-4-one

In the title compound, C19H16O3, the dihedral angle between the chromanone moiety and the methoxy phenyl ring is 16.47 (1)°. In the crystal, the molecules are linked by pairs of C—H...O hydrogen bonds, generating R 2 2(14) inversion dimers; further C—H...O hydrogen bonds connect the dimers into [100] double chains.

Tert-Butyl 4-{3-[6-(4-methoxyphenyl)-2-methylpyrimidin-4-yl]quinolin-2-yl}piperazine-1-carboxylate

The asymmetric unit of the title compound, C30H33N5O3, contains two independent molecules,AandB. In moleculeA, thetert-butyl 4-methylpiperazine-1-carboxylate group was refined as disordered over two sets of sites with an occupancy ratio of 0.821 (4):0.179 (4). The piperazine ring adopts a chair conformation in both molecules. The dihedral angles between the pyrimidine ring and methoxyphenyl ring are 20.27 (14) and 8.72 (11)° for moleculesAandB, respectively. The quinoline ring system makes dihedral angles of 30.68 (11) and 37.76 (10)° with the pyrimidine ring in moleculesAandB, respectively. In the crystal, C—H...O hydrogen bonds link the molecules into chains along [100].

3-[6-(4-Methoxyphenyl)-2-methylpyrimidin-4-yl]-2-(4-methylpiperazin-1-yl)quinoline

In the title compound, C26H27N5O, the piperazine ring adopts a chair conformation. The pyrimidine ring makes a dihedral angle of 1.5 (1)° with the methoxyphenyl ring and 33.1 (1)° with the quinoline ring system. In the crystal, molecules are consolidated in the crystal packing by weak C—H...π interactions and π–π stacking interactions.

6-Bromo-2-(4-methoxyphenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

In the title compound, C14H12BrN3O, the dihedral angle between the mean planes of the imidazo[4,5-b]pyridine ring system and the methoxyphenyl ring is 41.53 (12)°. In the crystal, weak C—H...N hydrogen bonds link the molecules into chains along the c-axis direction. Weak π–π stacking interactions involving the imidazole and the methoxyphenyl rings further stabilize the crystal packing.

Synthesis, single crystal structure and spectroscopic aspects of chalcone 2(2E)-1-(4′-bromobiphenyl-4-yl)-3-(2, 3-dimethoxybenzaldhyde) prop-2-ene-1-one

Abstract The title compound, (2E)-1-(4′-bromobiphenyl-4-yl)-3-(3,4-dichlorophenyl)-3-hydroxypropan-1-one (BDCP) was synthesized, spectrally characterized (IR, UV, FT-IR, 1H NMR, and FT-Raman), and its three- dimensional structure was confirmed by single crystal diffraction studies. In addition, Second Harmonic Generation (SHG) efficiency of the crystal, thermogravimetric analysis (TGA), and powder XRD were performed. The bromo phenyl ring makes a dihedral angle of 50.8 (2)0 and 34.5 (2)° with the methoxy phenyl ring and central phenyl moiety. The dihedral angle between the methoxy phenyl ring and the central phenyl moiety is 17.1(2)0. The short contacts C9—O1…Cg1 and C3—H3…Cg3 are involved in crystal structure stabilization. The SHG conversion of the BDCP is found to be 1.33 times that of Urea.

Ethyl 2-(4-methoxyphenyl)-1-methyl-1H-benzimidazole-5-carboxylate

In the title benzimidazole derivative, C18H18N2O3, the methoxyphenyl ring is twisted with respect to the benzimidazole ring system, making a dihedral angle of 28.81 (5)°. The pendant ethyl chain has an extended conformation. Within the imidazole ring, the C—N single bonds have a partial double-bond character. In the crystal, molecules are linked by weak C—H...π interactions and π–π stacking [the centroid-to-centroid distances being 3.6468 (7), 3.7279 (7) and 3.7481 (7) Å].

(Z)-2-(4-Methoxyanilino)-1,4-diphenylbut-2-ene-1,4-dione

In the molecule of the title compound, C23H19NO3, the mean plane of the methoxyphenyl ring makes dihedral angles of 51.63 (8) and 50.86 (8)° with the terminal phenyl rings. An intramolecular N—H...O hydrogen bond occurs. The crystal structure features C—H...O hydrogen bonds.

Synthesis, Crystal Structure, DFT Study of m-Methoxy-N′-(3-Methoxybenzoyl)-N-Phenylbenzohydrazide

The crystal structure of m-methoxy-N′-(m-anisoyl)-N-phenylbenzohydrazide has been determined by means of single-crystal X-ray diffraction. The title compound crystallizes in the monoclinic space group P 21/c with unit cell parameters: a = 8.7338(1), b = 24.5602(3), c = 9.6929(1) Å, β = 113.186(2)°, V = 1911.23(4) Å3, Z = 4. The dihedral angles between the mean plane of the central benzene ring and two terminal aromatic rings are 72.44(4)° and 89.90(4)°, respectively. The two methoxyphenyl rings are orthogonal with a dihedral angle of 89.74(4)°. The crystal packing is stabilized by a combination of N–H…O intermolecular hydrogen bonding and weak intermolecular C–H…O interactions. The X-ray structure was compared with the optimized counterpart calculated by the B3LYP/6-311G basis set and the results showed that the optimized geometry can reproduce the crystal structure parameters well.

Ethyl 1-benzyl-2-(4-methoxyphenyl)-1H-benzimidazole-5-carboxylate

The title benzimidazole derivative, C24H22N2O3, is T-shaped with the methoxyphenyl and benzyl rings inclined to the imidazole ring system (r.m.s. deviation = 0.009 Å) by 46.73 (10) and 88.88 (15)°, respectively. The phenyl ring and methoxyphenyl rings are inclined at an angle of 82.14 (16)°. In the crystal, weak C—H...O hydrogen bonds link the molecules into [101]C(14) chains.

Ethyl 1-(4-fluorobenzyl)-2-(4-methoxyphenyl)-1H-benzo[d]imidazole-5-carboxylate

The title benzoimidazole derivative, C24H21FN2O3, is T-shaped, with the methoxyphenyl and fluorobenzyl rings inclined to the benzoimidazole ring system by 40.91 (8) and 86.04 (8)°, respectively, indicating that the fluorobenzyl ring system is nearly orthogonal to the benzoimidazole ring system. The fluorobenzyl and methoxyphenyl rings are inclined to one another by 78.90 (10)°. In the crystal, molecules are linkedviatwo pairs of C—H...O hydrogen bonds, forming inversion dimers withR22(28) andR22(22) ring motifs. As a result of these hydrogen bonds, ribbons propagating along [010] are formed.

Synthesis, Spectroscopic Characterization and X-ray Structure Analysis of 6-(2,5-Dichlorothiophen-3-yl)-2-methoxy-4-(4-methoxyphenyl)pyridine-3-carbonitrile

The title compound was prepared by the condensation of an equimolar mixture of 1-(2,5-dichlorothiophen-3-yl)-3-(4-methoxyphenyl)prop-2-en-1-one, malononitrile and sodium hydroxide. The molecular structure was fully characterized using different spectroscopic methods. Mass ESI–HRMS measurements were performed. The HRESIMS analysis revealed the molecular formula, C18H12Cl2N2O2SNa, with [M + Na]+ and [M + Na + 2]+ and [M + Na + 4]+ isotopic clusters characteristic for a dichlorinated compound. The compound was also thoroughly characterized by 1H, 13C, NMR spectra and 2D NMR spectra (COSY, HSQC and HMBC). The molecular structure was confirmed by X-ray single crystal analysis. The new compound crystallizes in the orthorhombic, Pbcn space group with unit cell dimensions: a = 31.901(7) A, b = 15.412(4) A, c = 7.3655(14) A, V = 3621.3(13) A3 and Z = 8. In the title compound, the central pyridine ring carries four substituents, a thiophene ring, a methoxyphenyl ring, a carbonitrile group and a methoxy group. The dihedral angles between the planes of the pyridine ring, the thiophene ring and the methoxyphenyl ring are 36.66 and 40.18°, respectively. Intermolecular C–H···O/N, π···π and anion···π [Cl···π] interactions are found in the crystal structure. All interactions consolidate a three dimensional network. Synthesis, characterization, crystal, molecular structure, and crystal supramolecularity of 6-(2,5-dichlorothiophen-3-yl)-2-methoxy-4-(4-methoxyphenyl)pyridine-3-carbonitrile are reported.

2-[4-(4-Methoxyphenyl)-1,3-thiazol-2-yl]-2,3-dihydro-1H-isoindole-1,3-dione

In the title isoindole, C18H12N2O3S, the methoxyphenyl ring is oriented at an angle of 9.5 (1)° with respect to the thiazole ring. In the crystal, molecules are linkedviaC—H...O interactions, which formC(7) chains propagating along [010]. In addition to this, weak π–π interactions are also observed.