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Issue 26, 2020
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New silver (thio)semicarbazide derivatives: synthesis, structural features, and antimicrobial activity

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Abstract

Two novel semicarbazide [HL1, 1, 1-((4-nitrophenyl)(phenyl)methylene)semicarbazide] and thiosemicarbazide [HL2, 2, 1-((4-nitrophenyl)(phenyl)methylene)thiosemicarbazide] ligands were generated from 4-nitrobenzophenone and the corresponding (thio)semicarbazide precursors. Compounds 1 and 2 were fully characterized and their X-ray crystal structures were established. These organic derivatives were further applied as bioactive building blocks for the self-assembly synthesis of silver(I) coordination compounds. The reactions of silver(I) nitrate with HL1/HL2 in the presence of aqueous NH4OH resulted in new silver(I) coordination compounds formulated as [Ag(HL1)(NO3)]·H2O (3) and [Ag63-L2)6] (4). These complexes were characterized by standard methods (FT-IR, NMR, ESI-MS, and elemental analysis) as well as single-crystal X-ray diffraction. The structure of 3 features a two-coordinate silver(I) center with a distorted linear {AgNO} geometry, wherein an unusual coordination of HL1 through the nitrogen atom of the amine group is realized. The structure of 4 reveals a discrete Ag6 cluster composed of two joined trisilver(I) rings, wherein the three-coordinate Ag(I) centers adopt an {AgNS2} environment. The antimicrobial activity of 1–4 was screened against Gram-positive (S. epidermidis and S. aureus) and Gram-negative (P. aeruginosa and E. coli) bacteria. Compound 4 presented antimicrobial activity against Gram-positive bacteria, including the ability to impair biofilm formation. This study thus contributes to a still limited research area on the development of new silver coordination compounds with potential antibiofilm activity.

Graphical abstract: New silver (thio)semicarbazide derivatives: synthesis, structural features, and antimicrobial activity

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Article information


Submitted
21 Apr 2020
Accepted
26 May 2020
First published
27 May 2020

New J. Chem., 2020,44, 10924-10932
Article type
Paper

New silver (thio)semicarbazide derivatives: synthesis, structural features, and antimicrobial activity

T. A. Fernandes, V. André, A. S. Arol, Â. França, S. Mikhalyonok, N. Cerca and A. M. Kirillov, New J. Chem., 2020, 44, 10924
DOI: 10.1039/D0NJ02013C

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