Abstract
Reaction of 2,3-dihydroxy benzaldehyde with 2-({2-amino phenyl}diazenyl)phenol afforded the ligand 3-(2-(2-hydroxyphenyl)diazenyl)-4-alkylphenyliminomethyl)benzene-1,2-diol. Reaction of H2L with VOSO4. 5H2O gave the oxido-vanadium(IV) complexes [(L)VO], which exhibited a quasi-reversible oxidative cyclic voltammetric response in a V(IV)/V(V) oxidative process. The complexes act as catalysts in the oxidation of organic thioethers and bromination of phenol. Their cytotoxic properties were examined for three cancer cell lines.
References
1.
Sickerman N.S.
,
Hu Y.
and
Ribbe M.W.
, Chem. An Asian J. , 2017 , 12 , 1985 .
2.
Lodhi M.A.
,
Ashiq U.
,
Jamal R.A.
and
Khan K.M.
, J. Chem. Soc. Pakistan , 2015 , 37 , 549 .
3.
Costa Pessoa J.
,
Garribba E.
,
Santos M.F.A.
and
Santos-Silva T.
, Coord. Chem. Rev. , 2015 , 301–302 , 49 .
4.
Wever R.
,
Van D.H.
and
Michael A.
, Dalton Trans. , 2013 , 42 , 11778 .
5.
Prodanovic R.
,
Ostafe R.
,
Blanusa M.
and
Schwaneberg U.
, Anal. Bioanal. Chem. , 2012 , 404 , 1439 .
6.
Michibata H.
(ed.), Vanadium: biochemical and molecular biological approaches , Springer Science+Business Media , Dordrecht , 2012 .
7.
Majumder S.
,
Pasayat S.
,
Roy S.
,
Dash S.P.
,
Dhaka S.
,
Maurya M.R.
,
Reichelt M.
,
Reuter H.
,
Brzezinski K.
and
Dinda R.
, Inorg. Chim. Acta , 2018 , 469 , 366 .
8.
Tarakhovskaya E.R.
,
Bilova T.E.
and
Maslov Y.I.
, Phycologia , 2015 , 54 , 417 .
9.
Zampella G.
,
Bertini L.
and
De Gioia L.
, Chem. Comm. , 2014 , 50 , 304 .
10.
Saha U.
,
Si T.K.
,
Nandi P.K.
and
Mukherjea K.K.
, Inorg. Chem. Comm. , 2013 , 38 , 43 .
11.
Kaysser L.
,
Bernhardt P.
,
Nam S-J.
,
Loesgen S.
,
Ruby J.G.
,
Skewes-Cox P.
,
Jensen P.R.
,
Fenical W.
and
Moore B.S.
, J. Am. Chem. Soc. , 2012 , 134 , 11988 .
12.
Nicolai M.
,
Goncalves G.
,
Natalio F.
and
Humanes M.
, J. Inorg. Biochem. , 2011 , 105 , 887 .
13.
Cao Y-Z.
,
Wei D-M.
,
Ren D-X.
,
Chen C.
,
Xing Y-H.
and
Shi Z.
, Acta Phys. – Chim. Sin. , 2011 , 27 , 539 .
14.
Molinari J.E.
and
Wachs I.E.
, J. Am. Chem. Soc. , 2010 , 132 , 12559 .
15.
Da Silva J.A.L.
,
Frausto da Silva J.L.R.
and
Pombeiro A.J.L.
, Coord. Chem. Rev. , 2013 , 257 , 2388 .
16.
Aureliano M.
,
Henao F.
,
Tiago T.
,
Duarte R.O.
,
Baruah Moura B.
and
Crans D.C.
, Inorg. Chem. , 2008 , 47 , 5677 .
17.
Kirillova M.V.
,
Da Silva J.A.L.
,
Jose A.L.
,
Da Silva J.J.R.F.
,
Palavra A.F.
and
Pombeiro A.J.L.
, Adv. Synth. Cat. , 2007 , 349 , 1765 .
18.
Kazemi Z.
,
Amiri Rudbari H.
,
Mirkhani V.
,
Sahihi M.
,
Moghadam M.
,
Tangestaninejad S.
,
Mohammadpoor-Baltork I.
,
Kajani A.A.
and
Azimi G.
, Euro. J. Med. Chem. , 2017 , 135 , 230 .
19.
Kowalski S.
,
Hac S.
,
Wyrzykowski D.
,
Zauszkiewicz-Pawlak A.
and
Inkielewicz-Stepniak I.
, Oncotarget , 2017 , 8 , 60324 .
20.
Scalese G.
,
Correia I.
,
Benítez J.
,
Rostán S.
,
Marques F.
,
Mendes F.
,
Matos A.P.
,
Costa Pessoa J.
and
Gambino D.
, J. Inorg. Biochem. , 2017 , 166 , 162 .
21.
Mal S.K.
,
Chattopadhyay T.
,
Fathima A.
,
Purohit C.S.
,
Kiran M.S.
,
Nair B.U.
and
Ghosh R.
, Polyhedron , 2017 , 126 , 23 .
22.
Lovisari M.
,
Volpi G.
,
Marabello D.
,
Cadamuro S.
,
Deagostino A.
,
Diana E.
,
Barge A.
,
Gallicchio M.
,
Boscaro V.
and
Ghibaudi E.
, J. Inorg. Biochem. , 2017 , 170 , 55 .
23.
Nahari G.
,
Reytman L.
,
Vendier L.
,
Tshuva E.Y.
and
Lorber C.
, Euro. J. Inorg. Chem. , 2017 , 2017 , 1807 .
24.
Hong X-L.
,
Zeng M-H.
,
Liu L-J.
,
Ye X-L.
and
Yi D-S.
, J. Coord. Chem. , 2017 , 70 , 1438 .
25.
Kazemi Z.
,
Amiri Rudbari H.
,
Mirkhani V.
,
Sahihi M.
,
Moghadam M.
,
Tangestaninejad S.
,
Mohammadpoor-Baltork I.
,
Kajani A.A.
and
Azimi G.
, Euro. J. Med. Chem. , 2017 , 135 , 230 .
26.
Abdel-Rahman L.H.
,
Abu-Dief A.M.
,
Aboelez M.O.
,
Hassan A.M.
and
Azza A.
, J. Photochem. Photobio. B: Biology , 2017 , 170 , 271 .
27.
León I.E.
,
Díez P.
,
Baran E.J.
,
Etcheverry S.B.
,
Susana B.
and
Fuentes M.
, Metallomics , 2017 , 9 , 891 .
28.
Kowalski S.
,
Hac S.
,
Wyrzykowski D.
,
Zauszkiewicz-Pawlak A.
and
Inkielewicz-Stepniak I.
, Oncotarget , 2017 , 8 , 60324 .
29.
Doucette K.A.
,
Hassell K.N.
and
Crans D.C.
, J. Inorg. Biochem. , 2016 , 165 , 56 .
30.
Galani A.
,
Tsitsias V.
,
Stellas D.
,
Psycharis V.
,
Raptopoulou C.P.
and
Karaliota A.
, J. Inorg. Biochem. , 2015 , 142 , 109 .
31.
Ying P.
,
Zeng P.
,
Lu J.
,
Chen H.
,
Liao X.
and
Yang N.
, Chem. Biol. Drug Des. , 2015 , 86 , 926 .
32.
Kioseoglou E.
,
Petanidis S.
,
Gabriel C.
and
Salifoglou A.
, Coord. Chem. Rev. , 2015 , 301 , 87 .
33.
Pattanayak P.
,
Pratihar J.L.
,
Patra D.
,
Mitra S.
,
Bhattacharyya A.
,
Lee H.M.
and
Chattopadhyay S.
, Dalton Trans. , 2009 , 6220 .
34.
Pattanayak P.
,
Parua S.P.
,
Patra D.
,
Lai C.K.
,
Brandão P.
,
Felix V.
and
Chattopadhyay S.
, Inorg. Chim. Acta , 2015 , 429 122 .
35.
Pattanayak P.
,
Patra D.
,
Pratihar J.L.
,
Burrows A.
,
Mahon M.F.
and
Chattopadhyay S.
, Inorg. Chim. Acta , 2010 , 363 , 2865 .
36.
Pattanayak P.
,
Pratihar J.L.
,
Patra D.
,
Puranik V.G.
and
Chattopadhyay S.
, Polyhedron , 2008 , 27 , 2209 .
37.
Das U.
,
Pattanayak P.
,
Patra D.
,
Brandão P.
,
Felix V.
and
Chattopadhyay S.
, Polyhedron , 2016 , 110 , 165 .
38.
Pattanayak P.
,
Pratihar J.L.
,
Patra D.
,
Burrows A.
,
Mohan M.
and
Chattopadhyay S.
, Eur. J. Inorg. Chem. 2007 , 4263 .
39.
Palmajumder E.
,
Patra S.
,
Drew M.G.B.
and
Mukherjea K.K.
, New J. Chem. , 2016 , 40 , 8696 .
40.
Andersson M.
,
Conte V.
,
Furia F.D.
and
Moro S.
, Tet. Lett. , 1995 , 36 , 2675 .
41.
Das C.
,
Adak P.
,
Mondal S.
,
Sekiya R.
,
Kuroda R.
,
Gorelsky S.I.
and
Chattopadhyay S.K.
, Inorg. Chem. , 2014 , 53 , 11426 .
42.
Wang Y.
,
Lin X-M.
,
Bai F-Y.
and
Sun L-X.
, J. Mol. Struc. , 2017 , 1149 , 379 .
43.
Perrin D.D.
and
Armarego W.L.F.
, Purification of laboratory chemicals , 3rd edn, Pergamon , New York , 1988 .
44.
Allal C.
,
Favre G.
,
Couderc B.
,
Salicio S.
,
Sixou S.
,
Hamilton A.D.
,
Sebti S.M.
45.
Lajoie-Mazenc I.
and
Pradines A.
, J. Biol. Chem. , 2000 , 275 , 31001 .
46.
Ren G.
,
Doshi M.
,
Hack B.K.
,
Alexander J.J.
and
Quigg R.J.
, J. Biol. Chem. , 2002 , 277 , 48351 .
47.
Wagner B.K.
,
Kitami T.
,
Gilbert T.J.
,
Peck D.
,
Ramanathan A.
,
Schreiber S.L.
,
Golub T.R.
and
Mootha V.K.
, Nat. Biotechnol. , 2008 , 26 , 343 .
48.
Sheldrick G.M.
, Acta Crystallogr. , 2008 , A 64 , 112 .
49.
Sheldrick G.M.
, SHELXL-97, University of Göttingen , Göttingen, Germany , Program for the Refinement of Crystal Structures from Diffraction Data, 1997 .
