Synthesis and antimicrobial activity of copper(II) and silver(I) complexes of hydroxynitrocoumarins: X-ray crystal structures of [Cu(hnc) 2(H2O)2] · 2H2O and [Ag(hnc)] (hncH = 4-hydroxy-3-nitro-2H-chromen-2-one)

Bernadette S. Creaven; Denise A. Egan; Kevin Kavanagh; Malachy McCann; Mary Mahon; Andy Noble; Bhumika Thati; Maureen Walsh

doi:10.1016/j.poly.2005.03.006

Synthesis and antimicrobial activity of copper(II) and silver(I) complexes of hydroxynitrocoumarins: X-ray crystal structures of [Cu(hnc) ₂(H₂O)₂] · 2H₂O and [Ag(hnc)] (hncH = 4-hydroxy-3-nitro-2H-chromen-2-one)

Bernadette S. Creaven, Denise A. Egan, Kevin Kavanagh, Malachy McCann, Mary Mahon, Andy Noble, Bhumika Thati, Maureen Walsh

Research output: Contribution to journal › Article › peer-review

Abstract

[Cu(hnc)₂(H₂O)₂] • 2H₂O (1) [hncH = 4-hydroxy-3-nitro-2H-chromen-2-one] and [Ag(hnc)] (2) were prepared by deprotonating the hydroxy group of hncH with NaOH and then adding copper(II) chloride dihydrate and silver(I) nitrate, respectively. [Ag(hmnc)] (3) was synthesised in a similar manner [hmncH = 7-hydroxy-8-nitro-3-methyl-2H-chromen- 2-one]. The mixed-ligand Ag(I) complex [Ag(phen)₂hnc] (4) was prepared by treating silver(I) nitrate with 1,10-phenanthroline (phen) (1:1) and subsequent reaction with a solution containing hncH and NaOH. Molecular structures of 1 and 2 were determined by X-ray crystallography. The asymmetric unit in 1 contains two molecules of water in addition to one molecule of the copper complex. In 2 the asymmetric unit comprises one hnc^- ligand moiety bonded in a bidentate fashion to the silver(I) ion with additional interactions from three other coumarin ligands. The geometry is best described as pentagonal bipyramidal. While none of the coumarin-based ligands or the free copper salt showed any significant anti-microbial activity, AgNO₃ and its' phen and coumarin complexes exhibited good anti-microbial activity, particularly against the clinically important methicillin-resistant Staphylococcus aureus (MRSA) bacterium and also demonstrated good activity, comparable to that of the commercial fungicides clortrimazole and ketoconazole, against a clinical isolate of the fungal pathogen Candida albicans.

Original language	English
Pages (from-to)	949-957
Number of pages	9
Journal	Polyhedron
Volume	24
Issue number	8
DOIs	https://doi.org/10.1016/j.poly.2005.03.006
Publication status	Published - 2 Jun 2005

Keywords

Anti-microbial
Candida albicans
Copper(II)
Coumarin
Silver(I)
X-ray structure

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Creaven, B. S., Egan, D. A., Kavanagh, K., McCann, M., Mahon, M., Noble, A., Thati, B., & Walsh, M. (2005). Synthesis and antimicrobial activity of copper(II) and silver(I) complexes of hydroxynitrocoumarins: X-ray crystal structures of [Cu(hnc) ₂(H₂O)₂] · 2H₂O and [Ag(hnc)] (hncH = 4-hydroxy-3-nitro-2H-chromen-2-one). Polyhedron, 24(8), 949-957. https://doi.org/10.1016/j.poly.2005.03.006

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title = "Synthesis and antimicrobial activity of copper(II) and silver(I) complexes of hydroxynitrocoumarins: X-ray crystal structures of [Cu(hnc) 2(H2O)2] · 2H2O and [Ag(hnc)] (hncH = 4-hydroxy-3-nitro-2H-chromen-2-one)",

abstract = "[Cu(hnc)2(H2O)2] • 2H2O (1) [hncH = 4-hydroxy-3-nitro-2H-chromen-2-one] and [Ag(hnc)] (2) were prepared by deprotonating the hydroxy group of hncH with NaOH and then adding copper(II) chloride dihydrate and silver(I) nitrate, respectively. [Ag(hmnc)] (3) was synthesised in a similar manner [hmncH = 7-hydroxy-8-nitro-3-methyl-2H-chromen- 2-one]. The mixed-ligand Ag(I) complex [Ag(phen)2hnc] (4) was prepared by treating silver(I) nitrate with 1,10-phenanthroline (phen) (1:1) and subsequent reaction with a solution containing hncH and NaOH. Molecular structures of 1 and 2 were determined by X-ray crystallography. The asymmetric unit in 1 contains two molecules of water in addition to one molecule of the copper complex. In 2 the asymmetric unit comprises one hnc- ligand moiety bonded in a bidentate fashion to the silver(I) ion with additional interactions from three other coumarin ligands. The geometry is best described as pentagonal bipyramidal. While none of the coumarin-based ligands or the free copper salt showed any significant anti-microbial activity, AgNO3 and its' phen and coumarin complexes exhibited good anti-microbial activity, particularly against the clinically important methicillin-resistant Staphylococcus aureus (MRSA) bacterium and also demonstrated good activity, comparable to that of the commercial fungicides clortrimazole and ketoconazole, against a clinical isolate of the fungal pathogen Candida albicans.",

keywords = "Anti-microbial, Candida albicans, Copper(II), Coumarin, Silver(I), X-ray structure",

author = "Creaven, \{Bernadette S.\} and Egan, \{Denise A.\} and Kevin Kavanagh and Malachy McCann and Mary Mahon and Andy Noble and Bhumika Thati and Maureen Walsh",

year = "2005",

month = jun,

day = "2",

doi = "10.1016/j.poly.2005.03.006",

language = "English",

volume = "24",

pages = "949--957",

journal = "Polyhedron",

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}

Creaven, BS, Egan, DA, Kavanagh, K, McCann, M, Mahon, M, Noble, A, Thati, B & Walsh, M 2005, 'Synthesis and antimicrobial activity of copper(II) and silver(I) complexes of hydroxynitrocoumarins: X-ray crystal structures of [Cu(hnc) ₂(H₂O)₂] · 2H₂O and [Ag(hnc)] (hncH = 4-hydroxy-3-nitro-2H-chromen-2-one)', Polyhedron, vol. 24, no. 8, pp. 949-957. https://doi.org/10.1016/j.poly.2005.03.006

Synthesis and antimicrobial activity of copper(II) and silver(I) complexes of hydroxynitrocoumarins: X-ray crystal structures of [Cu(hnc) ₂(H₂O)₂] · 2H₂O and [Ag(hnc)] (hncH = 4-hydroxy-3-nitro-2H-chromen-2-one). / Creaven, Bernadette S.; Egan, Denise A.; Kavanagh, Kevin et al.
In: Polyhedron, Vol. 24, No. 8, 02.06.2005, p. 949-957.

Research output: Contribution to journal › Article › peer-review

TY - JOUR

T1 - Synthesis and antimicrobial activity of copper(II) and silver(I) complexes of hydroxynitrocoumarins

T2 - X-ray crystal structures of [Cu(hnc) 2(H2O)2] · 2H2O and [Ag(hnc)] (hncH = 4-hydroxy-3-nitro-2H-chromen-2-one)

AU - Creaven, Bernadette S.

AU - Egan, Denise A.

AU - Kavanagh, Kevin

AU - McCann, Malachy

AU - Mahon, Mary

AU - Noble, Andy

AU - Thati, Bhumika

AU - Walsh, Maureen

PY - 2005/6/2

Y1 - 2005/6/2

N2 - [Cu(hnc)2(H2O)2] • 2H2O (1) [hncH = 4-hydroxy-3-nitro-2H-chromen-2-one] and [Ag(hnc)] (2) were prepared by deprotonating the hydroxy group of hncH with NaOH and then adding copper(II) chloride dihydrate and silver(I) nitrate, respectively. [Ag(hmnc)] (3) was synthesised in a similar manner [hmncH = 7-hydroxy-8-nitro-3-methyl-2H-chromen- 2-one]. The mixed-ligand Ag(I) complex [Ag(phen)2hnc] (4) was prepared by treating silver(I) nitrate with 1,10-phenanthroline (phen) (1:1) and subsequent reaction with a solution containing hncH and NaOH. Molecular structures of 1 and 2 were determined by X-ray crystallography. The asymmetric unit in 1 contains two molecules of water in addition to one molecule of the copper complex. In 2 the asymmetric unit comprises one hnc- ligand moiety bonded in a bidentate fashion to the silver(I) ion with additional interactions from three other coumarin ligands. The geometry is best described as pentagonal bipyramidal. While none of the coumarin-based ligands or the free copper salt showed any significant anti-microbial activity, AgNO3 and its' phen and coumarin complexes exhibited good anti-microbial activity, particularly against the clinically important methicillin-resistant Staphylococcus aureus (MRSA) bacterium and also demonstrated good activity, comparable to that of the commercial fungicides clortrimazole and ketoconazole, against a clinical isolate of the fungal pathogen Candida albicans.

AB - [Cu(hnc)2(H2O)2] • 2H2O (1) [hncH = 4-hydroxy-3-nitro-2H-chromen-2-one] and [Ag(hnc)] (2) were prepared by deprotonating the hydroxy group of hncH with NaOH and then adding copper(II) chloride dihydrate and silver(I) nitrate, respectively. [Ag(hmnc)] (3) was synthesised in a similar manner [hmncH = 7-hydroxy-8-nitro-3-methyl-2H-chromen- 2-one]. The mixed-ligand Ag(I) complex [Ag(phen)2hnc] (4) was prepared by treating silver(I) nitrate with 1,10-phenanthroline (phen) (1:1) and subsequent reaction with a solution containing hncH and NaOH. Molecular structures of 1 and 2 were determined by X-ray crystallography. The asymmetric unit in 1 contains two molecules of water in addition to one molecule of the copper complex. In 2 the asymmetric unit comprises one hnc- ligand moiety bonded in a bidentate fashion to the silver(I) ion with additional interactions from three other coumarin ligands. The geometry is best described as pentagonal bipyramidal. While none of the coumarin-based ligands or the free copper salt showed any significant anti-microbial activity, AgNO3 and its' phen and coumarin complexes exhibited good anti-microbial activity, particularly against the clinically important methicillin-resistant Staphylococcus aureus (MRSA) bacterium and also demonstrated good activity, comparable to that of the commercial fungicides clortrimazole and ketoconazole, against a clinical isolate of the fungal pathogen Candida albicans.

KW - Anti-microbial

KW - Candida albicans

KW - Copper(II)

KW - Coumarin

KW - Silver(I)

KW - X-ray structure

UR - https://www.scopus.com/pages/publications/18844441696

U2 - 10.1016/j.poly.2005.03.006

DO - 10.1016/j.poly.2005.03.006

M3 - Article

AN - SCOPUS:18844441696

SN - 0277-5387

VL - 24

SP - 949

EP - 957

JO - Polyhedron

JF - Polyhedron

IS - 8

ER -