SÍNTESE, ESTRUTURAS DE TRIAZENO 1-ÓXIDO E COMPLEXO DE K+, E AVALIAÇÃO DA ATIVIDADE BIOLÓGICA DE 1-METILTRIAZENOS 1-ÓXIDO E 1,3-BIS(ARIL)TRIAZENOS / SYNTHESIS, STRUCTURE OF TRIAZENE 1-OXIDE AND COMPLEX OF K+, AND EVALUTION OF BIOLOGICAL ACTIVITY OF 1-METILTRIAZENES 1-OXIDE AND 1,3-BIS(ARIL)TRIAZENES

AUTOR(ES)
DATA DE PUBLICAÇÃO

2005

RESUMO

This work is associated with the crystal and molecular structure analysis of two free triazene 1-oxide molecules and a complex with K+ involving a p-carboxyfenil-substituted single protonated triazene 1-oxide ligand. 1-metil-3-(p-carboxyphenyl)triazene 1-oxide (1) crystallizes in the monoclinic system, space group C2/c, with cell parameters a = 27.2046(8) Å, b = 5.0218(1) Å, c = 14.4503(5) Å, β= 113.13(1), V = 1815.47(9)Å3, Z = 8, R1 = 0.0325, wR2 = 0.0977. The crystal structure demonstrate that the molecule deviate slightly from planarity (r.m.s. 0.0192 Å). The molecules are associated in form of a bidimensional supramolecular array in the [100] and [001] crystallographic directions via classic hydrogen bonds, NHO e OHO. 1,3-bis(4-carboxyphenyl)triazene (2) crystallizes in the monoclinic system, space group P21/c, with cell parameters a = 23.168(2) Å, b = 3.7398(4) Å, c = 19.751(2) Å, β= 100.912(6), V = 1680.3(3)Å3, Z = 4, R1 = 0.0764, wR2 = 0.2425. The crystal structure show that the molecule deviates significantly from planarity (r.m.s. 0.2071 Å). Also in this case, the molecules (2) are associated in form of a bidimensional supramolecular array constituted by helix chains including classic hydrogen bonds with water molecules, operated by a 21 axial screw-axis along the [010] crystallographic direction, and a c axial glide-plane in the [001] crystallographic direction. The complex 3-(4-carboxyphenyl)-1-metiltriazene 1-oxide of potassium tetrahydratade (4) crystallizes in the monoclinic system, space group P21/c, with cell parameters a = 12.695 Å, b = 8.123 Å, c = 13.520 Å, β = 106.71, V = 1335.3Å3, Z = 4, R1 = 0.0554, wR2 = 0.1705. The single crystal structure analysis demonstrate that the coordination sphere of the K+ ion include eight oxygen atoms belonging to the carboxyphenyl deprotonated triazene ligand, and seven water molecules. The coordination geometry identified correspond an S8 molecule with a distorted boat conformation. Additionally, molecule (1) were characterized by melting point and spectroscopic methods (IR, UV/VIS and multinuclear NMR), molecule (2) by melting point and complex (4) by melting point and spectroscopic methods (IR and UV/VIS). In connection with biological activity, molecule (1) demonstrate bacteriostatic activity (concentration of 16μg/mL), and acts as bactericide (concentration of 32μg/mL) in relation to the bacterium S. agalactiae. 1-(4-etoxyphenyl)-3-(4-carboxyphenyl)triazene (3) (concentration of 1,25mM) demonstrate 17,03% cleavage ability in relation to the plasmidial DNA pUC18.

ASSUNTO(S)

complex of k+ triazene 1-oxide atividade biológica triazeno 1-óxido biological activity complexo de k+ quimica

ACESSO AO ARTIGO

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