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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]
Copyright of Polyhedron is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.)
Database: Engineering Source
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DbLabel: Engineering Source
An: 138889875
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  Data: Synthesis, structure, and cytotoxicity studies of oxidovanadium(IV and V) complexes bearing chelating phenolates.
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  Data: <searchLink fieldCode="JN" term="%22Polyhedron%22">Polyhedron</searchLink>. Oct2019, Vol. 171, p1-9. 9p.
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  Data: <searchLink fieldCode="DE" term="%22Benzoates%22">Benzoates</searchLink><br /><searchLink fieldCode="DE" term="%22Sulfonic+acids%22">Sulfonic acids</searchLink><br /><searchLink fieldCode="DE" term="%22Benzoic+acid%22">Benzoic acid</searchLink><br /><searchLink fieldCode="DE" term="%22Molecular+structure%22">Molecular structure</searchLink><br /><searchLink fieldCode="DE" term="%22Crystal+structure%22">Crystal structure</searchLink><br /><searchLink fieldCode="DE" term="%22Acetonitrile%22">Acetonitrile</searchLink><br /><searchLink fieldCode="DE" term="%22Phenol%22">Phenol</searchLink>
– Name: Abstract
  Label: Abstract
  Group: Ab
  Data: 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]
– Name: AbstractSuppliedCopyright
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  Data: <i>Copyright of Polyhedron is the property of Pergamon Press - An Imprint of Elsevier Science and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.)
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RecordInfo BibRecord:
  BibEntity:
    Identifiers:
      – Type: doi
        Value: 10.1016/j.poly.2019.06.051
    Languages:
      – Code: eng
        Text: English
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      Pagination:
        PageCount: 9
        StartPage: 1
    Subjects:
      – SubjectFull: Benzoates
        Type: general
      – SubjectFull: Sulfonic acids
        Type: general
      – SubjectFull: Benzoic acid
        Type: general
      – SubjectFull: Molecular structure
        Type: general
      – SubjectFull: Crystal structure
        Type: general
      – SubjectFull: Acetonitrile
        Type: general
      – SubjectFull: Phenol
        Type: general
    Titles:
      – TitleFull: Synthesis, structure, and cytotoxicity studies of oxidovanadium(IV and V) complexes bearing chelating phenolates.
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            – D: 01
              M: 10
              Text: Oct2019
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