320408-75-1

Usage

Class

Organic compounds, specifically pyridinecarboxamides

Structure

Symmetric, with two diethylaminothioxomethyl groups attached to the N2 and N6 positions of the pyridine ring

Uses

Commonly used in pharmaceutical research and drug discovery as a potential inhibitor or substrate of enzymes, and as a building block in the synthesis of more complex chemical compounds

Biological and chemical properties

Still being studied and explored for potential applications in various fields.

Upstream product

• 58328-36-2 N,N-diethyl-N'-benzoyl-thiourea 
• 3739-94-4 2,6-Pyridinedicarbonyl dichloride 
• 7204-46-8 1,1-diethylthiourea 
• 499-83-2 Pyridine-2,6-dicarboxylic acid 
• 109-89-7 diethylamine 
• 109069-62-7 pyridine-2,6-dicarbonyl diisothiocyanate 

Relevant academic research and scientific papers

Trinuclear CoIILnIIICoII Complexes (Ln = La, Ce, Nd, Sm, Gd, Dy, Er, and Yb) with 2,6-Dipicolinoylbis(N, N-diethylthiourea): Synthesis, Structures, and Magnetism

One-pot reactions of 2,6-dipicolinoylbis(N,N-diethylthiourea) (H2L) with Co(CH3COO)2·4H2O and LnCl3, where Ln = La, Ce, Nd, Sm, Gd, Dy, Er, and Yb, in warm methanol in the presence of Et3N,

Synthesis, characterization and biological applications of bismuth(III) complexes with aroylthiourea ligands

This work describes the synthesis, structural characterization and biological applications of three new bismuth(III) complexes with aroylthiourea-based ligands: [Bi(La)3(HLa)] (1), [Bi2(Lb)4(μ-Lb)2]?2(C3H6O) (2), and [Bi6(μ-Lc)6(μ3-NO3)2(μ6-NO3)](NO3)3?4H2O (3), where HLa = N-benzoyl(N′,N′-diethylthiourea), HLb = N-benzoyl(morpholinylthiourea), and H2Lc = N2,N6-bis(diethylcarbamothioyl)pyridine-2,6-dicarboxamide. The ligands HLa and HLb were considered as monopodal, while H2Lc as bipodal. All compounds were characterized by melting point determination, Fourier-transform infrared spectroscopy (FTIR), proton proton and carbon-13 nuclear magnetic resonance spectroscopy (NMR), mass spectrometry (MS), elemental analysis (EA) and single-crystal X-ray diffraction (SC-XRD). Structural analysis showed that compound 1 was a mononuclear heptacoordinate complex, while compound 2 presented a dinuclear structure and compound 3 was built up by a hexanuclear framework. The proligands, the new complexes, and Bi(NO3)3?5H2O had their antibacterial activities evaluated against E. coli (ATCC 25922), S. aureus (ATCC 25923), and P. aeruginosa (ATCC 27853). The in vitro disk-diffusion (DD) method showed the ability of compound 2 to inhibit two types of bacteria (P. aeruginosa and S. aureus). In the results of minimum inhibitory concentration (MIC), all complexes showed significant activity against the tested microorganisms except for compound 1. The inorganic salt used for comparison showed antibacterial activity only against P. aeruginosa and the ligands showed no apparent activity. Compound 2 presented the best antibacterial activity among the tested substances, and its performance was remarkable even when compared to other similar compounds found in the literature, attesting the importance of targeting bismuth(III) aroylthioureas for further research on new drugs development.

Enthalpies of combustion of two bis(N,N-diethylthioureas)

The standard (p{ring operator} = 0.1 MPa) molar energies of combustion in oxygen, at T = 298.15 K, of two crystalline bis(N,N-diethylthioureas) R(CONHCSNEt2)2: pyridine-2,6-dicarbonyl-bis(N,N-diethylthiourea), R = pyridyl, abbreviated as (bis-py-DETU), and adipoyl-dicarbonyl-bis(N,N-diethylthiourea), R = (CH2)4, abbreviated as (bis-ad-DETU), were measured by rotating bomb calorimetry so, the standard molar enthalpies of formation of both compounds, in their crystalline phase, were derived. {A table is presented}Furthermore, the energetics of the title compounds were studied by means of density functional theory calculations at the B3LYP/ 6-311G(dp) level of theory.

Uranyl Complexes with Aroylbis(N, N-dialkylthioureas)

The reaction of isophthaloylbis(N,N-diethylthiourea), H2L1, with UO2(CH3COO)2·2H2O and NEt3 as a supporting base gives a tetranuclear, anionic complex of the composition [{UO2(L1)}4(OAc)2]2-, in which the uranyl ions are S,O-chelate bonded. Each two of them are additionally linked by an acetato ligand. Similar reactions of various uranyl starting materials (uranyl acetate, uranyl nitrate, (NBu4)2[UO2Cl4]) with corresponding pyridine-centered ligands (pyridine-2,6-dicarbonylbis(N,N-dialkylthioureas), H2L2) yield mononuclear, neutral compounds, in which the thiourea derivatives are coordinated as S,N,N,N,S-five-dentate chelators. The equatorial coordination spheres of the formed hexagonal bipyramidal complexes [UO2(L2)(solv)] are completed by solvent ligands (H2O, MeOH, or DMF). Attempted reactions without a supporting base result in decomposition of the organic ligands and the formation of hexanuclear uranyl complexes with pyridine-2,6-dicarboxylato ligands, while the use of an excess of base results in condensation and the formation of dinuclear [{UO2(L2)(μ-OMe)}2]2- complexes. A stable complex of the composition [UO2(L3)] results from reactions of common uranyl starting materials with 2,2′-bipyridine-6,6′-dicarbonylbis(N,N-diethylthiourea) (H2L3). The equatorial coordination sphere of the neutral, hexagonal bipyramidal complex is occupied by an SN4S donor atom set, which is provided by the hexadentate organic ligand. While the uranium complexes with {L1}2- and {L2}2- are labile and rapidly decompose in acidic solutions, [UO2(L3)] is stable over a wide pH range, and the ligand readily extracts uranyl ions from aqueous solutions into organic solvents.

Iron(III) Metallacryptand and Metallacryptate Assemblies Derived from Aroylbis(N,N-diethylthioureas)

The reaction of isophthaloylbis(N,N-diethylthiourea), H2L1, with FeCl3·6H2O gives the dinuclear tris-complex [Fe2(L1)3] (5), possessing a cryptand-like structure. A similar reaction with the ligand 2,6-dipicolinoylbis(N,N-diethylthiourea), H2L2, however, results in the formation of the anionic, mononuclear Fe(III) complex [Fe(L2)2]- (6), which could be isolated as its "Tl+ salt" by the subsequent addition of Tl(NO3). A tighter view to the solid state structure of the obtained product, however, characterizes compound 6 as a one-dimensional coordination polymer, in which four-coordinate Tl+ ions connect the {[Fe(L2)2]-} units to infinite chains. When Fe3+ ions and Tl+ ions are added to H2L2 simultaneously in a one-pot reaction, a different product is obtained: a cationic trinuclear complex of the composition {M?[Fe2(L2)3]}+. It has been isolated as a PF6- salt and represents a {2}-metallacryptate with a nine-coordinate Tl+ ion in the central void. Structurally related products of the compositions {M?[Fe2(L2)3]}(PF6) (M = Na+, K+, Rb+) (8(PF6)) could be isolated from analogous reactions with alkaline salts instead of Tl(NO3). {2}-Metallacryptates with larger central voids were synthesized with the ether-spaced aroylbis(N,N-diethylthiourea) H2L3. The compounds {M?[Fe2(L3)3]}(PF6) (M = K+, Rb+, Tl+ or Cs+) (9(PF6)) were prepared by a similar protocol like those with H2L2 with the simultaneous addition of the metal ions to a solution of H2L3. Due to the larger spacer between the aroylthiourea units, the coordination number of the central M+ ions is 12 by six carbonyl and six ether oxygen atoms. All products were characterized by elemental analysis, IR spectroscopy, and X-ray structure analysis. Cyclic voltammetric studies were carried out with the three representative complexes [Fe2(L1)3], {K?[Fe2(L2)3]}(PF6), and {K?[Fe2(L3)3]}(PF6). The obtained voltammograms indicate the dependence of the redox properties of the oligonuclear systems on the conjugation in the organic backbones of the ligands.