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Synthesis, structure, and cytotoxicity studies of oxidovanadium(IV and V) complexes bearing chelating phenolates.

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Title:	Synthesis, structure, and cytotoxicity studies of oxidovanadium(IV and V) complexes bearing chelating phenolates.
Authors:	Miller-Shakesby, David M.¹ (AUTHOR), Nigam, Shubhanchi¹ (AUTHOR), Brookfield, Adam¹ (AUTHOR), McInnes, Eric J.L.¹ (AUTHOR), Prior, Timothy J.¹ (AUTHOR), Archibald, Stephen J.¹ (AUTHOR) s.j.archibald@hull.ac.uk, Redshaw, Carl¹ (AUTHOR) c.redshaw@hull.ac.uk
Source:	Polyhedron. Oct2019, Vol. 171, p1-9. 9p.
Subjects:	Benzoates, Sulfonic acids, Benzoic acid, Molecular structure, Crystal structure, Acetonitrile, Phenol
Abstract:	The synthesis, characterization and crystal structures of oxidovanadium(IV and V) complexes with chelate phenoxide ligation derived from the compounds 2,6-bis(hydroxymethyl)-4-methylphenol, 6,6′-methylenebis(4- tert -butyl-2-(hydroxymethyl)phenol), 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid or 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzosulfonic acid are reported. The compounds were found to be of low toxicity using in vitro cell assays with 50% cytotoxicity values (CC50) values in the range 56–126 μM. The interaction of [VO(acac) 2 ] with 2,6-bis(hydroxymethyl)-4-methylphenol (L1 H 3) or 6,6′-methylenebis(4- tert -butyl-2-(hydroxymethyl)phenol) (L2 H 4) in refluxing toluene afforded, following work-up in ethanol, the complexes [VO L1 ] 2 (1) and {[VO(acac)(HOEt)](VO) L2 ]} 2 (2), respectively. Use of 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid (L3 H 2) or 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzosulfonic acid (L4 H 2) with [VOCl 3 ] in refluxing acetonitrile, followed by methanol and THF work-up, afforded the complexes [Et 3 NH][VO(OMe) L3 ] 2 (3) and [Et 3 NH][VO(OMe) L4 ] 2 (4), respectively. The interaction of [VOSO 4 ] and L3 H 2 in refluxing acetonitrile afforded, with extraction into methanol, the complex [VO(OMe) L3 ] 2 (5). The molecular structures of 2 , 3 and 5 have been determined; the structure of 1 has been reported previously. The complexes in this study have been determined to be of low toxicity using in vitro cell assays with 50% cytotoxicity values (CC 50) values in the range 56–126 µM. [ABSTRACT FROM AUTHOR]
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Database:	Engineering Source

Description
Abstract:	The synthesis, characterization and crystal structures of oxidovanadium(IV and V) complexes with chelate phenoxide ligation derived from the compounds 2,6-bis(hydroxymethyl)-4-methylphenol, 6,6′-methylenebis(4- tert -butyl-2-(hydroxymethyl)phenol), 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid or 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzosulfonic acid are reported. The compounds were found to be of low toxicity using in vitro cell assays with 50% cytotoxicity values (CC50) values in the range 56–126 μM. The interaction of [VO(acac) 2 ] with 2,6-bis(hydroxymethyl)-4-methylphenol (L1 H 3) or 6,6′-methylenebis(4- tert -butyl-2-(hydroxymethyl)phenol) (L2 H 4) in refluxing toluene afforded, following work-up in ethanol, the complexes [VO L1 ] 2 (1) and {[VO(acac)(HOEt)](VO) L2 ]} 2 (2), respectively. Use of 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzoic acid (L3 H 2) or 4-[3,5-bis(2-hydroxyphenyl)-1,2,4-triazol-1-yl]benzosulfonic acid (L4 H 2) with [VOCl 3 ] in refluxing acetonitrile, followed by methanol and THF work-up, afforded the complexes [Et 3 NH][VO(OMe) L3 ] 2 (3) and [Et 3 NH][VO(OMe) L4 ] 2 (4), respectively. The interaction of [VOSO 4 ] and L3 H 2 in refluxing acetonitrile afforded, with extraction into methanol, the complex [VO(OMe) L3 ] 2 (5). The molecular structures of 2 , 3 and 5 have been determined; the structure of 1 has been reported previously. The complexes in this study have been determined to be of low toxicity using in vitro cell assays with 50% cytotoxicity values (CC 50) values in the range 56–126 µM. [ABSTRACT FROM AUTHOR]
ISSN:	02775387
DOI:	10.1016/j.poly.2019.06.051