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Synthesis, characterization and antimicrobial studies of cadmium(II) complexes with a tetraazamacrocycle (\(\hbox {L}_{\mathrm{B}}\)) and its cyanoethyl N-pendent derivative \((\hbox {L}_{\mathrm{BX}}\))

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Abstract

An isomeric ligand, \(\hbox {L}_{\mathrm{B}}\) of 3,10-C-meso-\(\hbox {Me}_{8}\)[14]ane on alkylation reaction with excess acrylonitrile resulted in a stereoselective product trans-(3S,5S,10R,12R)-N1,N8-bis(2-cyanoethyl)-C-meso-derivative, \(\hbox {L}_{\mathrm{BX}}\). Reaction of \(\hbox {L}_{\mathrm{B}}\) with Cd(\(\hbox {ClO}_{4})_{2}\cdot 4\hbox {H}_{2}\hbox {O}\) in methanol gave the octahedral complex, [Cd(\(\hbox {L}_{\mathrm{B}})\)(\(\hbox {ClO}_{4})_{2}\)] whereas interaction of the ligand \(\hbox {L}_{\mathrm{BX}}\) with Cd(\(\hbox {NO}_{3})_{2}\cdot 4\hbox {H}_{2}\hbox {O}\) in methanol yielded a square pyramidal mononitratocadmium(II) nitrate complex, [Cd(\(\hbox {L}_{\mathrm{BX}})\)(\(\hbox {NO}_{3})\)](\(\hbox {NO}_{3})\) and an octahedral dinitratocadmium(II) complex, [Cd(\(\hbox {L}_{\mathrm{BX}})\)(\(\hbox {NO}_{3})_{2}\)]. The complexes, [Cd(\(\hbox {L}_{\mathrm{B}})\)(\(\hbox {ClO}_{4})_{2}\)] and [Cd(\(\hbox {L}_{\mathrm{BX}})\)(\(\hbox {NO}_{3})_{2}\)] underwent axial substitution reactions with KCNS and KBr to produce octahedral diisothiocyanatocadmium(II) complexes, [Cd(\(\hbox {L}_{\mathrm{B}})\)(NCS)\(_{2}\)] and [Cd(\(\hbox {L}_{\mathrm{BX}})\)(NCS)\(_{2}\)] and octahedral dibromidocadmium(II) complexes, [Cd(\(\hbox {L}_{\mathrm{B}})\hbox {(Br)}_{2}\)] and [Cd(\(\hbox {L}_{\mathrm{BX}})\hbox {(Br)}_{2}\)], respectively; whereas, [Cd(\(\hbox {L}_{\mathrm{BX}})\)(\(\hbox {NO}_{3})\)](\(\hbox {NO}_{3})\) underwent axial addition with KCl, simultaneous axial substitution and anion exchange with KCNS and simultaneous axial addition, substitution and anion exchange with \(\hbox {NaClO}_{4}\cdot 6\hbox {H}_{2}\hbox {O}\) to produce octahedral [Cd(\(\hbox {L}_{\mathrm{BX}})\)(\(\hbox {NO}_{3})\)Cl], square planar octahedral [Cd(\(\hbox {L}_{\mathrm{BX}})\)(\(\hbox {H}_{2}\hbox {O}\))\(_{2}\)](\(\hbox {ClO}_{4})_{2}\), respectively. The newly prepared compounds have been characterized by different analytical and spectroscopic methods. The antibacterial activities of the ligands, metal salts and complexes have been tested against two selected gram positive bacteria and two gram negative bacteria.

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References

  1. Rzuezek S G, Pilch D S, Liu A, Liu L, LaVoie E J and Rice J E MacrocyclicPyridylPolyoxazoles: Selective RNA and DNA G-Quadruplex Ligands as Antitumor Agents 2010 J. Med. Chem. 53 3632

  2. EI-Boraey H A and EL-Gammal O A 2015 New 15-membered tetraaza (N4) macrocyclic ligand and its transition metal complexes: Spectral, magnetic, thermal and anticancer activity Spectrochim. Acta A 138 553

    Article  Google Scholar 

  3. Shankarwar S G, Nagolkar B B, Shelke V A and Chondhekar T K 2015 Synthesis, spectral, thermal and antimicrobial studies of transition metal complexes of 14-membered tetraaza[N4] macrocyclic ligand Spectrochim. Acta A 145 188

    Article  CAS  Google Scholar 

  4. Gull P, Dar O A, Malik M A and Hashmi A A 2016 Design, synthesis, characterization and antimicrobial/antioxidant activities of 1,4-dicarbonyl-phenyl dihydrazide based macrocyclic ligand and its Cu(II), Co(II) and Ni(II) complexes Microb. Pathog. 237

  5. Nath B C, Suarez S, Doctorovich F, Roy T G and Baggio R 2013 Two solvatomorphic forms of a copper complex formulated as Cu(L)(\(\text{ ClO }_{4})_{2}\).2(\(\text{ H }_{2}\text{ O }\))(I) and Cu(L)(\(\text{ ClO }_{4})_{2}\)(II), where L is 3,10-Cmeso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane, \(\text{ C }_{18}\text{ H }_{40}\text{ N }_{4}\) Acta Cryst. C69 689

    Google Scholar 

  6. Roy T G, Hazari S K S, Dey B K, Sutradhar R, Dey L, Anowar N and Tiekink E R T 2006 Axial ligand substitution in diastereoisomeric trans-[Co(\(\text{ Me }_{8}\)[14]ane)\(\text{ Cl }_{2}\)]\(^{+}\)Complexes and their antifungal activities J. Coord. Chem. 59 351

    Article  CAS  Google Scholar 

  7. Roy T G, Hazari S K S, Dey B K, Nath B C, Dutta A, Olbrich F and Rehder D 2011 Syntheses, electrolytic behaviour and antifungal activities of Zn(II) complexes of isomers of 3,10-C-meso- 3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane (L). Crystal and molecular structure of [\(\text{ ZnL }_{{\rm B}}\)(\(\text{ NO }_{3})\)]\(\text{ NO }_{3}\)(\(\text{ L }_{{\rm B}}=a,e,a,e\)-L) Inorg. Chim. Acta 371 63

    Article  CAS  Google Scholar 

  8. Roy T G, Hazari S K S, Dey B K, Nath A, Kim D I and Park Y C 2007 Synthesis of some octahedral nickel(II) complexes of one isomer of isomeric Me8[14]anes: X-ray structure of diisothiocyanato (3,10-C-meso3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane, \(\text{ L }_{{\rm C}})\) nickel(II), [\(\text{ NiL }_{{\rm C}}\)(NCS)\(_{2}\)] J. Incl. Phen. Mac. Chem. 58 249

    Article  CAS  Google Scholar 

  9. Roy T G, Hazari S K S, Dey B K, Meah H A, Rahman M S, Kim D I and Park Y C 2007 Synthesis,electrolytic behaviour and antimicrobial activities of cadmium Complexes of isomers of 3,10-Cmeso- 3,5,7,7,10,12,14,14-octamethyl-1,4,8,11- tetraazacyclotetradecane J. Coord. Chem. 40 1567 1

    Google Scholar 

  10. Roy T G, Hazari S K S, Meah H A, Gupta S K D, Roy P G, Behrens U and Rehder D 2014 Synthesis and antimicrobial activities of copper(II) complexes of N(4),N(11)-dimethyl (\(\text{ L }_{{\rm BZ}}\) & \(\text{ L }_{{\rm CZ}})\) and N(4)-monomethyl(\(\text{ L }_{{\rm CZ1}}\)(-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane. Crystal and molecular structure of [\(\text{ CuL }_{{\rm CZ1}}\)](\(\text{ ClO }_{4})_{2}\) Inorg. Chim. Acta 415 124

    Article  CAS  Google Scholar 

  11. Roy T G, Hazari S K S, Dey B K, Meah H A, Bader C and Rehder D 2004 Copper(II) and nickel(II) complexes of N,N-bis(2-hydroxyethyl)-octamethyl-1,4,8,11-tetraaza-cyclotetradecane Eur. J. Inorg. Chem. 4115

  12. Miah H A 2005 Synthesis, characterization and antimicrobial activities of some new tetraazamacrocyclic ligands and their transition metal complexes (Ph.D. Thesis, Department of Chemistry, University of Chittagong, Bangladesh)

  13. Roy T G, Hazari S K S, Dey B K, Miah H A and Tiekink E R T 2001 Trans- (3S,5S,10R,12R)-1,8- bis (2-cyanoethyl)-C-meso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane Acta Cryst. E57 0524

    Google Scholar 

  14. Sengupta S K, Sahni S K and Kapoor R N 1983 Zinc(ii), cadmium(ii) and mercury(ii) complexes of macrocyclic ligands derived from 2,6-diacetylpyridine J. Coord. Chem. 12 113

    Article  CAS  Google Scholar 

  15. Beynek N, Uluçam G, Tüylü B A, Zeytinoğlu H and Benkli K. 2007 Synthesis and characterization of a new macrocyclic ligand and its copper (II), cadmium (II), and lead (II) complexes: genotoxic activity of these complexes in cultured human lymphocytes Drug Chem. Toxicol. 30 399

    Article  CAS  Google Scholar 

  16. Curtis N F, Swann S A, Waters T N and Maxwell I E 1969 Isomerism of some octamethyl-1,5,8,12-tetraazacyclotetradecadiene complexes of nickel(II) and copper(II) J. Am. Chem. Soc. 91 4588

    Article  CAS  Google Scholar 

  17. Bembi R, Sondhi S M, Singh A K, Jhanjii A K, Roy T G, Lown J W and Ball R G 1989 Polyazamacrocycles V. Structure of isomeric 3,5,7,7,10,12,14,14-octamethyl-1,4,8,11tetraazacyclotetradecanes Bull. Chem. Soc. Jpn. 62 3701

    Article  CAS  Google Scholar 

  18. Roy T G, Hazari S K S, Dey B K, Miah H A, Olbrich F and Rehder D 2007 Syntheses anantimicrobial activities of isomers of N(4), N(11)-dimethyl-3,10-C-meso-3,5,7,7,10,12,14,14-octamethyl-1,4,8,11-tetraazacyclotetradecane and their nickel(II)complexes Inorg. Chem. 46 5372

    Article  CAS  Google Scholar 

  19. Silverstein R M 1967 Mass Spectrometry 2\(^{nd}\) edn. (New York: John Wiley and Sons) p.4

    Google Scholar 

  20. Greenwood N N and Straughan B P and Wilson A E 1968 Behaviour of tellurium(IV) chloride, bromide, and iodide in organic solvents and the structures of the species present J. Chem. Soc. A 2209

  21. Farago M E and James J M 1965 Coordination of Thiocyanate and Selenocyanate in Some Diamine Complexes of Nickel(II) and Copper(II) Inorg. Chem. 4 1706

    Article  CAS  Google Scholar 

  22. Sabatini A and Bertin I 1965 Infrared Spectra between 100 and 2500 \(\text{ Cm }^{.-1}\) of Some Complex Metal Cyanates, Thiocyanates, and Selenocyanates Inorg. Chem. 4 959

    Article  CAS  Google Scholar 

  23. Bembi R, Drew M G B, Singh R and Roy T G 1991 Polyazamacrocycles. 9.Characterization of diastereoisomeric trans-(Co(\(\text{ Me }_{8}\)[14]ane)\(\text{ Cl }_{2}\)]+ complexes Inorg. Chem. 30 1403

    Article  CAS  Google Scholar 

  24. Roy T G, Hazari S K S, Dey, B K, Dutta, S, Monsur M A and Tiekink E R T 2006 Axial addition in diastereoisomeric [Cu(\(\text{ Me }_{8}\)[14]ane)](\(\text{ ClO }_{4})_{2}\)] complexes: Anti-fungal and antibacterial activities J. Coord. Chem. 59 1757

    Article  CAS  Google Scholar 

  25. Biswas F B, Roy T G, Rahman M A and Emran T B 2014 An in vitro antibacterial and antifungal effects of cadmium(II) complexes of hexamethyltetraazacyclotetradecadiene ligands Asian Pac. J. Trop. Biomed. 4 S618

    Article  Google Scholar 

  26. Salehi M and Hasanzadeh M 2015 Characterization, crystal structures, electrochemical and antibacterial studies of four new binuclear cobalt(III) complexes derived from o-aminobenzyl alcohol Inorg. Chim. Acta 426 6

    Article  CAS  Google Scholar 

  27. Dharmaraj N, Viswanathamurthi and Nataranjan K 2001 Ruthenium(II) complexes containing bidentate Schiff bases and their antifungal activity Trans. Met. Chem. 26 105

    Article  CAS  Google Scholar 

  28. Jorgensen J H and Ferraro M J 2009 Antimicrobial susceptibility testing: a review of general principles and contemporary practices Clin. Infect. Dis. 49 1749

    Article  CAS  Google Scholar 

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Acknowledgements

Authors would like to thank the University Grant Commission, Bangladesh for awarding a Research Grant to TGR.

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  1. Md Masudur Rahman

    Present address: Anti-corruption Commission, 1/Shegunbagicha, Dhaka, Bangladesh

Authors and Affiliations

  1. Department of Chemistry, University of Chittagong, Chittagong, 4331, Bangladesh

    Md Shah Alam, Saswata Rabi, Md Masudur Rahman, Adrity Baidya, Manashi Debi & Tapashi Ghosh Roy

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Alam, M.S., Rabi, S., Rahman, M.M. et al. Synthesis, characterization and antimicrobial studies of cadmium(II) complexes with a tetraazamacrocycle (\(\hbox {L}_{\mathrm{B}}\)) and its cyanoethyl N-pendent derivative \((\hbox {L}_{\mathrm{BX}}\)). J Chem Sci 130, 35 (2018). https://doi.org/10.1007/s12039-018-1438-z

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