Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide
For the first time, a thiosemicarbazone-type ligand containing a paracetamol structural unit was synthesized. Five new coordination compounds based on copper(II) salts: [Cu(L)CH<sub>3</sub>COO] (<b>1</b>), [{Cu(L)Cl}<sub>2</sub>]·H<sub>2</sub>O (<b&...
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MDPI AG
2023-10-01
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| Series: | Inorganics |
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| Online Access: | https://www.mdpi.com/2304-6740/11/10/408 |
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| author | Roman Rusnac Olga Garbuz Yurii Chumakov Victor Tsapkov Christelle Hureau Dorin Istrati Aurelian Gulea |
| author_facet | Roman Rusnac Olga Garbuz Yurii Chumakov Victor Tsapkov Christelle Hureau Dorin Istrati Aurelian Gulea |
| author_sort | Roman Rusnac |
| collection | DOAJ |
| description | For the first time, a thiosemicarbazone-type ligand containing a paracetamol structural unit was synthesized. Five new coordination compounds based on copper(II) salts: [Cu(L)CH<sub>3</sub>COO] (<b>1</b>), [{Cu(L)Cl}<sub>2</sub>]·H<sub>2</sub>O (<b>2</b>), [Cu(L)H<sub>2</sub>O·DMF]NO<sub>3</sub> (<b>3</b>), [Cu(L)Br] (<b>4</b>), [Cu(L)H<sub>2</sub>O]ClO<sub>4</sub> (<b>5</b>), were obtained, where <b>HL</b> is <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide. The new <b>HL</b> was characterized by NMR, FTIR, spectroscopy, and X-ray crystallography. All copper(II) coordination compounds were characterized by elemental analysis, FTIR, EPR spectroscopy, and molar electrical conductivity. Furthermore, single crystal X-ray diffraction analysis elucidated the structures of thiosemicarbazone <b>HL</b> as well as complexes <b>1–3</b>. All compounds were tested for antimicrobial, antifungal, and antioxidant activities, and their toxicity to <i>Daphnia magna</i> was studied. Biological evaluation has revealed that most of the synthesized compounds demonstrate promising antibacterial, antifungal, and antioxidant activities. In many cases, their antibacterial/antifungal activity is comparable to that of certain drugs used in medicine for these purposes, and in some cases, even surpasses them. <b>HL</b> and complexes <b>2–5</b> exhibit antioxidant activity that surpasses that of Trolox. Furthermore, <b>HL</b> and complex <b>2</b> display virtually no toxicity to <i>D. magna.</i> |
| first_indexed | 2024-03-10T21:10:57Z |
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| institution | Directory Open Access Journal |
| issn | 2304-6740 |
| language | English |
| last_indexed | 2024-03-10T21:10:57Z |
| publishDate | 2023-10-01 |
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| series | Inorganics |
| spelling | doaj.art-8fcb9a23e02d484592571f72aa65868e2023-11-19T16:49:15ZengMDPI AGInorganics2304-67402023-10-01111040810.3390/inorganics11100408Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamideRoman Rusnac0Olga Garbuz1Yurii Chumakov2Victor Tsapkov3Christelle Hureau4Dorin Istrati5Aurelian Gulea6Laboratory of Advanced Materials in Biopharmaceutics and Technics, Moldova State University, 60 Mateevici Street, MD-2009 Chisinau, MoldovaLaboratory of Advanced Materials in Biopharmaceutics and Technics, Moldova State University, 60 Mateevici Street, MD-2009 Chisinau, MoldovaLaboratory of Physical Methods of Solid State Investigation “Tadeusz Malinowski”, Institute of Applied Physics, MD-2028 Chisinau, MoldovaLaboratory of Advanced Materials in Biopharmaceutics and Technics, Moldova State University, 60 Mateevici Street, MD-2009 Chisinau, MoldovaLaboratoire de Chimie de Coordination UPR 8241, Centre National de la Recherche Scientifique, 31400 Toulouse, FranceDepartment of Dentistry, University of Medicine and Pharmacy “Nicolae Testemitanu”, 165 Stefan cel Mare si Sfant Bd., MD-2004 Chisinau, MoldovaBiological Invasions Research Center, Institute of Zoology, Moldova State University, 1 Academiei Street, MD-2028 Chisinau, MoldovaFor the first time, a thiosemicarbazone-type ligand containing a paracetamol structural unit was synthesized. Five new coordination compounds based on copper(II) salts: [Cu(L)CH<sub>3</sub>COO] (<b>1</b>), [{Cu(L)Cl}<sub>2</sub>]·H<sub>2</sub>O (<b>2</b>), [Cu(L)H<sub>2</sub>O·DMF]NO<sub>3</sub> (<b>3</b>), [Cu(L)Br] (<b>4</b>), [Cu(L)H<sub>2</sub>O]ClO<sub>4</sub> (<b>5</b>), were obtained, where <b>HL</b> is <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide. The new <b>HL</b> was characterized by NMR, FTIR, spectroscopy, and X-ray crystallography. All copper(II) coordination compounds were characterized by elemental analysis, FTIR, EPR spectroscopy, and molar electrical conductivity. Furthermore, single crystal X-ray diffraction analysis elucidated the structures of thiosemicarbazone <b>HL</b> as well as complexes <b>1–3</b>. All compounds were tested for antimicrobial, antifungal, and antioxidant activities, and their toxicity to <i>Daphnia magna</i> was studied. Biological evaluation has revealed that most of the synthesized compounds demonstrate promising antibacterial, antifungal, and antioxidant activities. In many cases, their antibacterial/antifungal activity is comparable to that of certain drugs used in medicine for these purposes, and in some cases, even surpasses them. <b>HL</b> and complexes <b>2–5</b> exhibit antioxidant activity that surpasses that of Trolox. Furthermore, <b>HL</b> and complex <b>2</b> display virtually no toxicity to <i>D. magna.</i>https://www.mdpi.com/2304-6740/11/10/408coordination compoundthiosemicarbazonecrystal structureantioxidant activityantimicrobial activityantifungal activity |
| spellingShingle | Roman Rusnac Olga Garbuz Yurii Chumakov Victor Tsapkov Christelle Hureau Dorin Istrati Aurelian Gulea Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide Inorganics coordination compound thiosemicarbazone crystal structure antioxidant activity antimicrobial activity antifungal activity |
| title | Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide |
| title_full | Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide |
| title_fullStr | Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide |
| title_full_unstemmed | Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide |
| title_short | Synthesis, Characterization, and Biological Properties of the Copper(II) Complexes with Novel Ligand: <i>N</i>-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide |
| title_sort | synthesis characterization and biological properties of the copper ii complexes with novel ligand i n i 4 2 1 pyridin 2 yl ethylidene hydrazinecarbothioyl amino phenyl acetamide |
| topic | coordination compound thiosemicarbazone crystal structure antioxidant activity antimicrobial activity antifungal activity |
| url | https://www.mdpi.com/2304-6740/11/10/408 |
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