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Bischelated complexes of a dithiocarbazate N,S Schiff base ligand: synthesis, characterization and antimicrobial activities

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Abstract

The N,S bidentate proligand S-hexyl-β-N-(4-methoxybenzylidene)dithiocarbazate (HL), obtained by condensation of S-hexyldithiocarbazate with 4-methoxybenzaldehyde, has been used to synthesize six metal complexes, namely NiL2, CuL2, ZnL2, CdL2, PdL2 and PbL2, which have been characterized by physicochemical techniques and spectroscopic methods. Single crystal structural analyses for NiL2, CuL2 and PdL2 show that these are square-planar complexes with each metal bischelated by the Schiff base in its deprotonated monoanionic form. In all three cases, the ligands show a trans configuration, although they crystallize in different space groups. All the metal complexes with the exception of the nickel derivative show a significant decrease in fluorescence intensity with respect to the free proligand HL. Free HL and all six complexes were tested for antibacterial activity against three pathogenic gram-negative organisms. The metal complexes show moderate although diverse activities; however, free HL as well as the copper(II) complex did not reveal any antibacterial activity against the tested organisms.

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References

  1. Hogarth G (2005) Transition metal dithiocarbamates: 1978–2003. In: Karlin KD (ed) Progress in inorganic chemistry, vol 53. Wiley, Hoboken

    Google Scholar 

  2. Qiu X-Y, Zhang C, Li S-Z, Cao G-X, Qu P, Zhang F-Q, Ma J-G, Zhai B (2014) Inorg Chem Commun 46:202–206

    Article  CAS  Google Scholar 

  3. How FN-F, Crouse KA, Tahir MIM, Tarafder MTH, Cowley AR (2008) Polyhedron 27:3325–3329

    Article  CAS  Google Scholar 

  4. Biswal D, Pramanik NR, Chakrabarti S, Drew MGB, Mitra P, Acharya K, Biswas S, Mondal TK (2015) New J Chem 39:8681–8694

    Article  CAS  Google Scholar 

  5. Low ML, Maigre L, Tahir MIM, Tiekink ERT, Dorlet P, Guillot R, Ravoof TB, Rosli R, Pages J-M, Policar C, Delsuc N, Crouse KA (2016) Eur J Med Chem 120:1–12

    Article  CAS  Google Scholar 

  6. Low ML, Maigre L, Dorlet P, Guillot R, Pagès J-M, Crouse KA, Policar C, Delsuc N (2014) Bioconjug Chem 25:2269–2284

    Article  CAS  Google Scholar 

  7. Low ML, Paulus G, Dorlet P, Guillot R, Rosli R, Delsuc N, Crouse KA, Policar C (2015) Biometals 28:553–566

    Article  CAS  Google Scholar 

  8. Md Yusof EN, Ravoof TBSA, Tiekink ERT, Veerakumarasivam A, Crouse KA, Tahir MIM, Ahmad H (2015) Int J Mol Sci 16:11034–11054

    Article  Google Scholar 

  9. Kundu S, Mondal D, Bhattacharya K, Endo A, Sanna D, Garribba E, Chaudhury M (2015) Inorg Chem 54:6203–6215

    Article  CAS  Google Scholar 

  10. Qiu X-Y, Li S-Z, Shi A-R, Li Q-Q, Zhai B (2012) Chin J Struct Chem 31:555–561

    CAS  Google Scholar 

  11. Bharti N, Maurya MR, Naqvi F, Azam A (2000) Bioorg Med Chem Lett 10:2243–2245

    Article  CAS  Google Scholar 

  12. Bharti N, Maurya MR, Naqvi F, Bhattacharya A, Bhattacharya S, Azam A (2000) Eur J Med Chem 35:481–486

    Article  Google Scholar 

  13. Maurya MR, Khurana S, Azam A, Zhang W, Rehder D (2003) Eur J Inorg Chem 1966–1973

  14. Pramanik NR, Chakraborty M, Biswal D, Mandal SS, Ghosh S, Chakrabarti S, Sheldrick WS, Drew MGB, Mondal TK, Sarkar D (2015) Polyhedron 85:196–207

    Article  CAS  Google Scholar 

  15. Bharati P, Bharti A, Chaudhari UK, Bharty MK, Kashyap S, Singh UP, Singh NK (2015) Inorg Chim Acta 425:100–107

    Article  CAS  Google Scholar 

  16. Begum MS, Howlader MBH, Miyatake R, Zangrando E, Sheikh MC (2015) Acta Cryst E71:o199

    Google Scholar 

  17. Rigaku (2010). Crystal structure. Version 4.0. Rigaku Corporation, Tokyo

  18. Sheldrick GM (2008) Acta Cryst A64:112–122

    Article  Google Scholar 

  19. Rigaku (1995) ABSCOR. Rigaku Corporation, Tokyo

    Google Scholar 

  20. Watkin DM, Pearce L, Prout CK (1993) CAMERON.Chemical Crystallography Laboratory. University of Oxford, Oxford

    Google Scholar 

  21. Farrugia LJ (1999) J Appl Crystallogr 32:837–838

    Article  CAS  Google Scholar 

  22. Zangrando E, Begum MS, Howlader MBH, Sheikh MC, Miyatake R (2016) IUCrData 1:x160521

    Article  Google Scholar 

  23. Gülcan M, Sönmez M, Berber İ (2012) Turk J Chem 36:189–200

    Google Scholar 

  24. Valgas C, de Souza SM, Smânia EFA, Smânia A Jr (2007) Braz J Microbiol 38:369–380

    Article  Google Scholar 

  25. Tarafder MTH, Khoo T-J, Crouse KA, Ali AM, Yamin BM, Fun H-K (2002) Polyhedron 21:2691–2698

    Article  CAS  Google Scholar 

  26. Takjoo R, Takjoo R, Yazdanbakhsh M, Kaju AA, Yaguang C (2010) Chin J Chem 28:221–228

    Article  CAS  Google Scholar 

  27. Singh RV, Mitharwal P, Singh R, Mital SP (2014) Am Chem Sci J 4:117–137

    Article  Google Scholar 

  28. Shaker SA, Mohammed HA, Salih AA (2010) Aust J Basic Appl Sci 4:5178–5183

    CAS  Google Scholar 

  29. da Maia PIS, de Fernandes AGA, Silva JJN, Andricopulo AD, Lemos SS, Lang ES, Abram U, Deflon VM (2010) J Inorg Biochem 104:1276–1282

    Article  CAS  Google Scholar 

  30. Roy S, Mandal TN, Barik AK, Gupta S, Butcher RJ, Nethaji M, Kar SK (2008) Polyhedron 27:593–601

    Article  CAS  Google Scholar 

  31. Takjoo R, Centore R, Ramasami LRP (2012) J Coord Chem 65:1569–1579

    Article  CAS  Google Scholar 

  32. Pramanik NR, Ghosh S, Raychaudhuri TK, Ray S, Butcher RJ, Mandal SS (2004) Polyhedron 23:1595–1603

    Article  CAS  Google Scholar 

  33. Roy S, Mandal TN, Barik AK, Pal S, Gupta S, Hazra A, Butcher RJ, Hunter AD, Zeller M, Kar SK (2008) Polyhedron 26:2603–2611

    Article  Google Scholar 

  34. Khaledi H, Ali HM, Olmstead MM (2011) Inorg Chim Acta 366:233–240

    Article  CAS  Google Scholar 

  35. Islam MAAAA, Sheikh MC, Alam MS, Zangrando E, Alam MA, Tarafder MTH, Miyatake R (2014) Transit Met Chem 39:141–149

    Article  CAS  Google Scholar 

  36. Islam MAAAA, Tarafder MTH, Sheikh MC, Alam MA, Zangrando E (2011) Transit Met Chem 36:531–537

    Article  CAS  Google Scholar 

  37. Yazdanbakhsh M, Takjoo R, Frank W, Kaju AA (2009) J Coord Chem 62:3651–3660

  38. Ravoof TBSA, Crouse KA, Tahir MIM, How FNF, Rosli R, Watkins DJ (2010) Transit Met Chem 35:871–876

    Article  CAS  Google Scholar 

  39. Jang YJ, Lee UK, Kweon B (2011) Bull Korean Chem Soc 26:925–929

    Google Scholar 

  40. Kumaran JS, Priya S, Jayachandramoni N, Mahalakshmi S (2013) J Chem, Article ID 260358:1–10

  41. Singh K, Kushawaha SK, Bharty MK, Dulare R, Butcher RJ (2009) J Mol Struc 936:257–263

    Article  CAS  Google Scholar 

  42. Ali MA, Tan AL, Mirza AH, Santos JH, Abdullah AHBH (2012) Transit Met Chem 37:651–659

    Article  CAS  Google Scholar 

  43. Jorge FE, Autschbach J, Ziegler T (2003) Inorg Chem 42:8902–8910

    Article  CAS  Google Scholar 

  44. Majumder A, Rosair GM, Mallick A, Chattopadhyay N, Mitra S (2006) Polyhedron 25:1753–1762

    Article  CAS  Google Scholar 

  45. Önal Z, Zengin H, Sönmez M (2011) Turk J Chem 35:905–914

    Google Scholar 

  46. Aazam ES, Husseiny AFEL, Al-Amri HM (2012) Arab J Chem 5:45–53

    Article  CAS  Google Scholar 

  47. Anitha C, Sheela CD, Tharmaraj P, Shanmugakala R (2013) Int J Inorg Chem, Article ID 436275:1–10

  48. Das D, Chand BG, Sarker KK, Dinda J, Sinha C (2006) Polyhedron 25:2333–2340

    Article  CAS  Google Scholar 

  49. Zangrando E, Begum MS, Sheikh MC, Miyatake R, Hossain MM, Alam MM, Hasnat MA, Halim MA, Ahmed S, Rahman MN, Ghosh A (2017) Arab J Chem 10:172–184

    Article  CAS  Google Scholar 

  50. Zangrando E, Islam MT, Islam MAAAA, Sheikh MC, Tarafder MTH, Miyatake R, Zahan R, Hossain MA (2015) Inorg Chim Acta 427:278–284

    Article  CAS  Google Scholar 

  51. Dronskowski R (2005) Computational chemistry of solid state materials. WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

    Book  Google Scholar 

  52. Hummel W, Huml K, Burgi H-B (1988) Helv Chim Acta 71:1291–1302

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The author M. S. Begum thanks the Department of Chemistry, Shahjalal University of Science and Technology, Sylhet-3114, Bangladesh, for laboratory facilities, and MCS thanks the Department of Applied Chemistry, Faculty of Engineering, University of Toyama, Japan, for analytical facilities.

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Authors and Affiliations

  1. Department of Chemistry, Shahjalal University of Science and Technology, Sylhet, 3114, Bangladesh

    M. S. Begum

  2. Department of Chemical and Pharmaceutical Sciences, Via L. Giorgieri 1, 34127, Trieste, Italy

    E. Zangrando

  3. Department of Applied Chemistry, Faculty of Engineering, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan

    M. C. Sheikh

  4. Center for Environmental Conservation and Research Safety, University of Toyama, 3190 Gofuku, Toyama, 930-8555, Japan

    R. Miyatake

  5. Department of Chemistry, Rajshahi University, Rajshahi, 6205, Bangladesh

    M. B. H. Howlader

  6. Department of Biochemistry and Molecular Biology, Shahjalal University of Science and Technology, Sylhet, 3114, Bangladesh

    M. N. Rahman & A. Ghosh

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  1. M. S. Begum
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  2. E. Zangrando
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  3. M. C. Sheikh
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  7. A. Ghosh
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Correspondence to M. S. Begum.

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Begum, M.S., Zangrando, E., Sheikh, M.C. et al. Bischelated complexes of a dithiocarbazate N,S Schiff base ligand: synthesis, characterization and antimicrobial activities. Transit Met Chem 42, 553–563 (2017). https://doi.org/10.1007/s11243-017-0160-x

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