Synthesis of nonperipherally tetra-[5-(diethylamino)-2-formylphenoxy] substituted metallophthalocyanines and their electrochemistry.

3-[5-(diethylamino)-2-formylphenoxy]phthalonitrile ( n-TY-CN ), metallophthalocyanines n-TY-Co , n-TY-Cu , and n-TY-Mn bearing [5-(diethylamino)-2-formylphenoxy] groups at nonperipheral positions were prepared for the first time. These compounds were characterized with IR, NMR (only for n-TY-CN ), mass and UV-vis (except n-TY-CN ) spectroscopy. Voltammetric characterizations of n-TY-Co , n-TY-Cu , and n-TY-Mn revealed that while n-TY-Co , n-TY-Cu , and n-TY-Mn showed characteristic Pc ring and/or metal-based reduction reaction, n-TY-Co , n-TY-Cu , and n-TY-Mn were coated on the working electrode during the oxidation processes owing to the cationic electropolymerizations of the [5-(diethylamino)-2-formylphenoxy] substituents.

Bis benzothiophene Schiff bases: synthesis and in silico-guided biological activity studies.

Since benzo [ b ] thiophene scaffold is one of the privileged structures in drug discovery as this core exhibitsactivities for different biological problems, in this study bis (benzo[ b ]thiophene-2-yl) alkyl methanimine derivatives (1-9) were synthesized by reacting benzo[ b ]thiophene-2-carbaldehyde with diamines. All newly compounds were characterized by IR, 1H NMR and 13C NMR spectroscopic methods. Synthesized compounds were investigated using binary QSARbased models on therapeutic activity prediction of synthesized compounds and they showed high predicted activities in following diseases: bacterial, angina, allergy, depression and obesity. Thus, they were then tested for their antimicrobial and antileishmanial activities as a result of this theoretical study. Compound 1(N, N'- (propane-1,3-diyl) bis (1-(benzo [ b ] thiophene-2-yl)) methanimine) was found the most active compound in both diseases. Thus, its molecular docking studies were also carried out.

Synthesis of Novel Symmetrical 1,4-Disubstituted 1,2,3-Bistriazole Derivatives via 'Click Chemistry' and Their Biological Evaluation.

A series of symmetric bis-1,2,3-triazole compounds 2-5(a-f) were synthesized as potential antioxidant agents via click chemistry. Their structures were confirmed by ¹H-NMR and (13)C-NMR. All of the synthesized compounds were subjected to antioxidant and antimicrobial assays. The antioxidant activity of these compounds (AChE inhibition, DPPH and SOD activities) was evaluated. Compound 2f was found to show the highest AChE inhibition activity of all compounds, while compound 3b showed a strong inhibitory effect on DPPH radical and compound 2a was the most effective of all compounds for SOD activity. All synthesized compounds were found to possess moderate antibacterial activity against the bacteria E. coli and Y.pseudotuberculosis.

Synthesis and biological properties of novel triazole-thiol and thiadiazole derivatives of the 1,2,4-Triazole-3(5)-one class.

2,2'-(4,4'(Butane-1,4-diyl/hexane-1,6-diyl)bis(3-methyl-5-oxo-4,5-dihydro-1,2,4- triazole-4,1-diyl)) diacetohydrazides 3a,b were obtained via the formation of diethyl 2,2'-(4,4'(butane-1,4-diyl/hexane-1,6-diyl)bis(3-methyl-5-oxo-4,5-dihydro-1,2,4-triazole-4,1- diyl))diacetates 2a,b, obtained starting from di-[3(methyl-2-yl-methyl)-4,5-dihydro-1H-[1,2,4]-triazole-5-one-4yl]-n-alkanes 1a,b in two steps. The synthesis of the compounds 7a,b-9a,b incorporating the 1,3,4-thiadiazole, and 10a,b-11a,b with a 1,2,4-triazole-thiol nucleus as the second heterocycle, was performed by the acidic or basic treatment of compounds 4a,b-6a,b which were obtained from the reaction of 3a,b with several isothiocyanates. Newly synthesized compounds were screened for antimicrobial activities and their antioxidant properties by the 1,1-diphenyl-2-picryl hydrazyl (DPPH) radical scavenging method. Compounds 4a,b, 5a,b, and 6a,b were found to possess good antioxidant properties. Almost all compounds have significant antimicrobial activities.

Synthesis, structural characterization and comparison of experimental and theoretical results by DFT level of molecular structure of 4-(4-methoxyphenethyl)-3,5-dimethyl-4H-1,2,4-triazole.

4-(4-Methoxyphenethyl)-3,5-dimethyl-4H-1,2,4-triazole (3) was synthesized from the reaction of ethyl N'-acetylacetohydrazonate (1) with 2-(4-methoxyphenyl)ethanamine (2). The structure of the title compound 3 has been inferred through IR, (1)H/(13)C NMR, mass spectrometry, elemental analyses and combination of X-ray crystallography and theoretical methods. In addition to the molecular geometry from X-ray determination, the molecular geometry and vibrational frequencies of the title compound 3 in the ground state, were calculated using the density functional method (B3LYP) with the 6-31G(d) basis set. The calculated results show that the optimized geometry can well reproduce the crystal structure and the theoretical vibrational frequencies show good agreement with experimental values. The nonlinear optical properties are also addressed theoretically. The predicted nonlinear optical properties of 3 are greater than ones of urea. In addition, DFT calculations of molecular electrostatic potentials and frontier molecular orbitals of the title compound were carried out at the B3LYP/6-31G(d) level of theory.

4-[2-(4-Hy-droxy-phen-yl)eth-yl]-3-propyl-1H-1,2,4-triazol-5(4H)-one.

The asymmetric unit of the title compound, C(13)H(17)N(3)O(2), contains eight crystallographically independent mol-ecules. The planes of the benzene and triazole rings in the eight mol-ecules make dihedral angles of 5.53 (13), 9.33 (13), 19.28 (11), 17.36 (8), 12.84 (12), 8.03 (8), 19.97 (11), and 7.98 (8)°. The eight mol-ecules in the asymmetric unit are linked by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds, forming a three-dimensional network.

4-(4-Meth-oxy-pheneth-yl)-3,5-diphenyl-4H-1,2,4-triazole.

In the title compound, C(23)H(21)N(3)O, the dihedral angles formed by the mean plane of the triazole ring [maximum deviation = 0.007 (1) Å] and the three phenyl rings are 51.13 (8), 52.84 (8) and 47.04 (8)°. In the crystal, mol-ecules are linked by weak C-H⋯N inter-actions, forming infinite chains propagating along the b-axis direction.

4-[2-(4-Meth-oxy-phen-yl)eth-yl]-3-(thio-phen-2-ylmeth-yl)-1H-1,2,4-triazol-5(4H)-one monohydrate.

In the title compound, C(16)H(17)N(3)O(2)S·H(2)O, the triazole ring makes a dihedral angle of 34.63 (6)° with the benzene ring. The thio-phene ring is disordered over two orientations [occupancy ratio = 0.634 (4):0.366 (4)] which make dihedral angles of 54.61 (16) and 54.57 (31)° with the triazole ring. Inter-molecular N-H⋯O and O-H⋯O hydrogen bonds stabilize the crystal structure.

Ethyl 4-(3-ethyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)benzoate.

In the title compound, C(13)H(15)N(3)O(3), the dihedral angle between the two aromatic ring is 51.06 (1)°. In the crystal, mol-ecules are connected by pairs of N-H⋯O hydrogen bonds into centrosymmetric dimers.

3,3'-Dimethyl-4,4'-(hexane-1,6-di-yl)bis-[1H-1,2,4-triazol-5(4H)-one].

The title compound, C(12)H(20)N(6)O(2), has a centre of symmetry. The mol-ecule consists of two triazole rings joined by an aliphatic -(CH(2))(6)- chain. The crystal structure is stabilized by inter-molecular N-H⋯O hydrogen bonds and by π-π stacking inter-actions between the triazole rings of inversion-related mol-ecules [centroid-centroid distance = 3.277 (8) Å].

4-(4-Meth-oxy-pheneth-yl)-3-methyl-1H-1,2,4-triazol-5(4H)-one.

The dihedral angle between the two rings in the title compound, C(12)H(15)N(3)O(2), is 49.03 (1)°. The crystal structure is stabilized by inter-molecular N-H⋯O and C-H⋯O hydrogen bonds and π-π stacking inter-actions between the triazole rings with a centroid-centroid distance of 3.394 Å.

3-Ethyl-4-[3-(1H-imidazol-1-yl)prop-yl]-5-phenyl-4H-1,2,4-triazole dihydrate.

In the title compound, C(16)H(19)N(5)·2H(2)O, the triazole ring makes dihedral angles of 70.61 (6) and 41.89 (8)°, respectively, with the imidazole and benzene rings. The water mol-ecules are involved in inter-molecular O-H⋯N and O-H⋯O hydrogen bonds, which stabilize the crystal packing.

4-[3-(1H-Imidazol-1-yl)prop-yl]-3-methyl-5-(thio-phen-2-ylmeth-yl)-4H-1,2,4-triazole monohydrate.

In the title compound, C(14)H(17)N(5)S·H(2)O, the triazole ring makes dihedral angles of 48.15 (8) and 84.92 (8)° with the imidazole and thio-phenyl rings, respectively. The water mol-ecule is involved in inter-molecular O-H⋯N hydrogen bonding.