Synthesis and structural characterization of a zinc(II) complex of the mycobactericidal drug isoniazid – Toxicity against Artemia salina

Freitas, Maria Clara Ramalho; António, Joseneide M.S.; Ziolli, Roberta Lourênço; Yoshida, María Irene; Rey, Nicolás A.; Diniz, Renata

doi:10.1016/j.poly.2011.04.027

Cited by 28 publications

(22 citation statements)

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“…The angle between hydrazide and pyridine is 21.3(3)°with Zn-Zn distance of 9.1833(8) Å. The literature [11] reports that when INH is coordinated in similar way, this angle decreases with increasing Zn-Zn distance, 44.7(1)°with distance of 9.105(2) Å and 36.7(1)°with distance of 9.161(2) Å. This angle in the INH2 molecules in 1 is in agreement with this tendency, despite the different conformations observed in comparison to the structure already reported [11].…”

Section: Resultsmentioning

confidence: 92%

“…The literature [11] reports that when INH is coordinated in similar way, this angle decreases with increasing Zn-Zn distance, 44.7(1)°with distance of 9.105(2) Å and 36.7(1)°with distance of 9.161(2) Å. This angle in the INH2 molecules in 1 is in agreement with this tendency, despite the different conformations observed in comparison to the structure already reported [11]. There are also some hydrogen bonds that help to stabilize its conformation, highlighted in figure S5 (N2-H2C⋅⋅⋅O23, N2-H2D⋅⋅⋅O9, and N1-H1A⋅⋅⋅O25).…”

Section: Resultsmentioning

confidence: 99%

“…There are also some reported structures with INH coordinated to transition metal ions [9][10][11][12]; the hydrogen bond networks are different to those observed in the INH structure, mainly due to coordination and the presence of counter ions which contain acceptor atoms for hydrogen bonds, like ClO 4 , and/or water molecules in the structure. Another difference occurs because the nitrogen of pyridine is coordinated and does not form hydrogen bonds like in free INH.…”

Section: Introductionmentioning

confidence: 95%

“…In the other one, INH coordinates also by pyridine forming a distorted tetrahedral coordination geometry [10]. When INH coordinates to zinc [11], both hydrazide and pyridine groups are coordinated, changing the INH conformation. This change is related to the angle between hydrazide and pyridine group which may increase with a decrease in zinc-zinc distance [11] coordinated at both groups.…”

Section: Introductionmentioning

confidence: 99%

“…When INH coordinates to zinc [11], both hydrazide and pyridine groups are coordinated, changing the INH conformation. This change is related to the angle between hydrazide and pyridine group which may increase with a decrease in zinc-zinc distance [11] coordinated at both groups. The zinc ion presents a distorted octahedral geometry; this geometry will also be expected in the compound formed and described in this work.…”

Section: Introductionmentioning

confidence: 99%

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Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺

Almeida

Silva

Abreu

et al. 2015

Journal of Coordination Chemistry

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2015) Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn 2+ and MnAn anti-tuberculosis drug, isonicotinohydrazide (INH), is studied concerning its conformation in different crystalline environments. In the present work, compounds with zinc (1) and manganese (2) ions are reported where INH has different conformations, caused by hydrogen bonds with 1,4-benzenedicarboxylic acid (H 2 BDC) and water molecules and by coordination bonds involving its functional groups. In 1, INH is coordinated to two zinc ions, where H 2 BDC and crystallization water molecules form several hydrogen bonds giving rise to a complex three-dimensional (3-D) network. In 2, both INH and H 2 BDC molecules are coordinated to manganese as well as four water molecules. The complex formed interacts by hydrogen bonds forming a 2-D arrangement. A 3-D network extension arises from other hydrogen bonds generated by crystallization water. In these two compounds, the presence of BDC ion and water molecules is very important in the stabilization of the complexes and in INH conformation. This work is focused on the structural description of formed compounds.

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Section: Resultsmentioning

confidence: 92%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺

Almeida

Silva

Abreu

et al. 2015

Journal of Coordination Chemistry

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Transition metal complexes of a hydrazone–oxime ligand containing the isonicotinoyl moiety: Synthesis, characterization and microbicide activities

Shakdofa

El‐Saied

Rasras

et al. 2018

Applied Organom Chemis

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Complexes of VO2+, Mn2+, Co2+, Ni2+, Cu2+, Zn2+, Ru3+ and UO22+ with (3‐(hydroxyimino)butan‐2‐ylidene)isonicotinohydrazide were synthesized and characterized using physical and spectral methods. Analytical data revealed that the complexes formed in 1:1 or 1:2 metal–ligand ratios. Spectral studies showed that the ligand bonded to the metal ion in neutral tridentate, monobasic tridentate or monobasic bidentate fashion through azomethine nitrogen atom, protonated/deprotonated imine oxime group and/or ketonic/enolic carbonyl group. From the electronic spectral data together with magnetic susceptibility values a square planar, tetrahedral or distorted octahedral structure can be proposed for all complexes. Electron spin resonance spectra for Cu2+ complexes (2–4) revealed axial symmetry with g|| > g⊥ > ge, indicating distorted octahedral or square planar structures and the unpaired electron exists in a dx2−y2 orbital with marked covalent bond feature. The prepared complexes showed good to excellent biological activity, and the most active complexes against Aspergillus niger were 4 and 9 with zone of inhibition of 25 and 23 mm, respectively. Complexes 10 and 11 showed interesting activity against Escherichia coli with zone of inhibition of 44 and 32 mm, respectively.

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Structural and Topological Study of Two Coordination Polymers Formed by 1,2,4,5 – Benzenetetracarboxylic Acid, Isonicotinylhydrazine and Metallic Ions Co²⁺ and Zn²⁺

et al. 2016

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In this work it is highlighted the structural and topological study of two coordination polymers formed by 1,2,4,5-Benzenetetracarboxylic acid (H 4 BTC), Isonicotinylhydrazine (INH) and metallic ions Co 2 + and Zn 2 + . Even formed by the same ligands, these coordination polymers are very different. The polymer formed by ligands and Co 2 + (compound 1), forms as a 3D coordination polymer and it crystalline stability is due to its coordination bonds. On the other hand, the compound formed by ligands and Zn 2 + (compound 2), forms a 1D coordination polymer and it is mainly stabilized by hydrogen bonds. Due to these facts, their structures present different and interesting topologies. Other interesting difference is related to coordination mode of H 4 BTC ligand. In compound 1, the H 4 BTC ligand is coordinated by carboxylate groups to cobalt ion by a monodentate way and by a bidentate bridge way. However, in compound 2 the H 4 BTC coordinates to zinc ion in a bidentate way by two different carboxylate groups. In both compounds the INH ligand coordinates in the same way to the metallic sites.

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Synthesis and structural characterization of a zinc(II) complex of the mycobactericidal drug isoniazid – Toxicity against Artemia salina

Cited by 28 publications

References 20 publications

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺

Transition metal complexes of a hydrazone–oxime ligand containing the isonicotinoyl moiety: Synthesis, characterization and microbicide activities

Structural and Topological Study of Two Coordination Polymers Formed by 1,2,4,5 – Benzenetetracarboxylic Acid, Isonicotinylhydrazine and Metallic Ions Co²⁺ and Zn²⁺

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Synthesis and structural characterization of a zinc(II) complex of the mycobactericidal drug isoniazid – Toxicity against Artemia salina

Cited by 28 publications

References 20 publications

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn2+ and Mn2+

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn2+ and Mn2+

Transition metal complexes of a hydrazone–oxime ligand containing the isonicotinoyl moiety: Synthesis, characterization and microbicide activities

Structural and Topological Study of Two Coordination Polymers Formed by 1,2,4,5 – Benzenetetracarboxylic Acid, Isonicotinylhydrazine and Metallic Ions Co2+ and Zn2+

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Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺

Isonicotinohydrazide conformation in a supramolecular system with 1,4-benzenedicarboxylic acid and Zn²⁺ and Mn²⁺

Structural and Topological Study of Two Coordination Polymers Formed by 1,2,4,5 – Benzenetetracarboxylic Acid, Isonicotinylhydrazine and Metallic Ions Co²⁺ and Zn²⁺