NS  Vol.4 No.3 , March 2012
Synthesis, spectral, 3D molecular modeling and antibacterial studies of dibutyltin (IV) Schiff base complexes derived from substituted isatin and amino acids
ABSTRACT
New dibutyltin(IV) complexes of Schiff base derived from 5-chloroindoline-2,3-dione, indoline- 2,3-dione with amino acids (tryptophan, alanine and valine) were synthesized and characterized by elemental analysis, IR, electronic spectra, conductance measurements, and biological activity. The analytical data showed that the Schiff base ligand acts as bidentate towards metal ions via the azomethine nitrogen and carboxylate oxygen by a stoichiometric reaction of M:L (1:2) to form metal complexes. NMR (1H, 13C and 119Sn) spectral data of the ligands and metal complex agree with proposed structures. The conductivity values between 14 - 27 ohm-1cm2mol-1 in DMF imply the presence of non-electrolyte species. 3D molecular modeling and analysis of bond lengths and bond angles have also been conducted for a representative compound, [Bu2Sn(L2)2], to substantiate the proposed structures. Antibacterial results indicate that the metal complexes are more active than the free ligands.

Cite this paper
Singh, H. and Singh, J. (2012) Synthesis, spectral, 3D molecular modeling and antibacterial studies of dibutyltin (IV) Schiff base complexes derived from substituted isatin and amino acids. Natural Science, 4, 170-178. doi: 10.4236/ns.2012.43025.
References
[1]   Li, C., Kanehisa, N., Miyagi, Y., Nakao, Y., Takamizawa, S., Mori, W. and Kai, Y. (1997) Syntheses, structures, and properties of the dinuclear copper(II) and nickel(II) complexes bridged by an alkoxide and a pyridazine or a phthalazine. Bulletin of the Chemical Society of Japan, 70, 2429-2436. doi:10.1246/bcsj.70.2429

[2]   Ibrahim, E.S., Sallam, S.A., Orabi, A.S., El-Shetary, B.A. and Lentz, A. (1998) Schiff bases of acetone derivatives: Spectroscopic properties and physical constants. Monatshefte fur Chemie, 129, 159-171. doi:10.1007/PL00010152

[3]   Campos, A., Anacona, J.R. and Campos, M.M. (1999) Synthesis and IR study of a Zn(II) complex containing a tetradentate macrocyclic Schiff base Ligand antifungal properties. Main Group Metal Chemistry, 22, 283-288. doi:10.1515/MGMC.1999.22.5.283

[4]   Sengupta, S.K., Pandey, O.P., Rai, A. and Sinha, A. (2006) Synthesis, spectroscopic, thermal and antifungal studies on lanthanum(III) and praseodymium(III) derivatives of 1,1-diacetylferrocenyl hydrazones. Spectrochimica Acta A, 65, 139-142. doi:10.1016/j.saa.2005.09.037

[5]   Qi, G.-F., Yang, Z.-Y and Wang, B.-D. (2007) Synthesis, characterization and DNA-binding properties of zinc(II) and nickel(II) Schiff base complexes. Transition Metal Chemistry, 32, 233-239. doi:10.1007/s11243-006-0160-8

[6]   Singh, V. P. and Katiyar, A. (2008) Synthesis, spectral characterization and antimicrobial activity of some transition metal(II) complexes with acetone p-amino acetophenone benzoylhydrazone. Pesticide Biochemistry and Physiology, 92, 8-14. doi:10.1016/j.pestbp.2008.04.003

[7]   Cozzi, P. G. (2004) Metal-Salen Schiff base complexes in catalysis: Practical aspects. Chemical Society Reviews, 33, 410-421. doi:10.1039/b307853c

[8]   Iqbal, A., Siddiqui, H.L., Ashraf, C.M., Bukhar, M.H. and Akram, C.M. (2007) Synthesis, spectroscopic and cytotoxic studies of biologically active new Schiff Bases derived from p-nitrobenzaldehyde. Chemical and Pharma- ceutical Bulletin, 55, 1070-1072. doi:10.1248/cpb.55.1070

[9]   Offiong, O.E. and Martelli, S. (1997) Stereochemistry and antitumour activity of platinum metal complexes of 2-acetylpyridine thiosemicarbazones. Transition Metal Chemistry, 22, 263-269. doi:10.1023/A:1018416624951

[10]   Maurya, R.C., Rajput, S. and Martin, H. (2006) Metal chelates as oral potential insulin adjuvants: Studies on some oxovanadium(IV) chelates involving biomimetic ono-donor sugars. Medicinal Chemistry Research, 15, 82- 83.

[11]   Singh, H.L. and Varshney, A.K. (2006) Synthetic, structural, and biochemical studies of organotin (IV) with schiff bases having nitrogen and sulphur donor ligands. Bioinorganic Chemistry and Applications, 2006, 1-7. doi:10.1155/BCA/2006/23245

[12]   Singh, H.L., Sharma, M. and Varshney, A.K. (2000) Stud- ies on coordination compounds of organotin (IV) with Schiff bases of amino acids. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 30, 445-456.

[13]   Siddiqi, H.L., Iqbal, A., Ahmad, S. and Weaver, W. (2006) Synthesis and spectroscopic studies of New Schiff bases. Molecules, 11, 206-211. doi:10.3390/11020206

[14]   Kim, S.-H., Gwon, S.-Y., Burkinshaw, S. M. and Son, Y.-A. (2010) The synthesis and proton-induced spectral switching of a novel azine dye and its boron complex. Dyes and Pigments, 87, 268-271. doi:10.1016/j.dyepig.2010.04.006

[15]   Kumbhar, A.S., Padhye, S.B., West, D.X. and Liberta, A.E. (1991) Electrochemical studies of copper(II) 2-ace- tylpyridine4N-dialkylthiosemicarbazones.Relation to their spectral, magnetic, and biological properties. Transition Metal Chemistry, 16, 276-279. doi:10.1007/BF01032852

[16]   Gielen, M. (2002) Review: Organotin compounds and their therapeutic potential. Applied Organometallic Chemistry, 16, 481-494. doi:10.1002/aoc.331

[17]   Gielen, M., Biesemans, M. and Willem, R. (2005) Or- ganotin compounds: From kinetics to stereochemistry and antitumour activities Applied Organometallic Chemistry, 19, 440-450. doi:10.1002/aoc.771

[18]   Valent, A., Melník, M., Hudecová, D., Dudová, B., Kivek?s, R. and Sundberg, M.R. (2002) Copper(II) salicylideneglycinate complexes as potential antimicrobial agents. Inorganica Chimica Acta, 340, 15-20. doi:10.1016/S0020-1693(02)01062-9

[19]   Nath, M., Singh, H., Eng, G. and Song, X. (2011) Interaction of organotin(IV) moieties with nucleic acid constituent: Synthesis, structural characterization and anti- inflammatory activity of tri-i-propyltin(IV) and diorganotin(IV) derivatives of guanosine. Inorganic Chemistry Communications, 14, 1381-1385. doi:10.1016/j.inoche.2011.05.027

[20]   Pellerito, C., Nagy, L., Pellerito, L. and Szorcsik, A.C. (2006) Biological activity studies on organotin(IV)n+ complexes and parent compounds. Journal of Organometallic Chemistry, 691, 1733-1747. doi:10.1016/j.jorganchem.2005.12.025

[21]   Ahmad, M. S., Hussain, M., Hanif, M., Ali, S. and Mirza, B. (2007) Synthesis, chemical characterization and biological screening for cytotoxicity and antitumor activity of organotin (IV) derivatives of 3,4-methylenedioxy 6-nitrophenylpropenoic acid. Molecules, 12, 2348-2363. doi:10.3390/12102348

[22]   Saxena, A. and Tandon, J. P. (1983) Antitumor activity of some diorganotin and tin(IV) complexes of Schiff bases. Cancer Letters, 19, 73-76. doi:10.1016/0304-3835(83)90138-6

[23]   Baul, T.S.B., Paul, A., Pellerito, L., Scopelliti, M., Singh, P., Verma, P., Duthie, A., De Vos, D. and Tiekink, E.R.T. (2011) Dibutyltin(IV) complexes containing arylazobenzoate ligands: Chemistry, in vitro cytotoxic effects on human tumor cell lines and mode of interaction with some enzymes. Investigational New Drugs, 29, 285-299. doi:10.1007/s10637-009-9360-3

[24]   Sadiq-ur-Rehman, Shahid, K., Ali, S., Bhatti, M. H. and Parvez, M. (2005) Organotin esterification of (E)-3-(3- fluoro-phenyl)-2-(4-chlorophenyl)-2-propenoic acid: Synthesis, spectroscopic characterization and in vitro biological activities. Crystal structure of [Ph3Sn(OC(O)C (4-ClC6H4) = CH(3-FC6H4))]. Journal of Organometallic Chemistry, 690, 1396-1408. doi:10.1016/j.jorganchem.2004.12.004

[25]   Perrin, D.D., Armarego, W.L.F. and Perrin, D.L. (1998) Purification of laborartory chemicals. 3rd Edition, Pergamon, London.

[26]   Singh, H.L., Singh, J.B. and Sharma, K.P. (2012) Synthetic, structural, and antimicrobial studies of organotin (IV) complexes of semicarbazone, thiosemicarbazone de- rived from 4-hydroxy-3-methoxybenzaldehyde. Research on Chemical Intermediates, 38, 53-65. doi:10.1007/s11164-011-0325-8

[27]   Ran, X., Wang, L., Cao, D., Lin, Y. and Hao, J. (2010) Synthesis, characterization and in vitro biological activity of cobalt(II), copper(II) and zinc(II) Schiff base complexes derived from salicylaldehyde and D,L-selenome-thionine. Applied Organometallic Chemistry, 25, 9-15. doi:10.1002/aoc.1680

[28]   Singh, K., Kumar, Y. and Pundir, R.K. (2010) Synthesis and Characterization of biologically active organosilicon (IV) complexes with schiff bases derived from o-amino- thiophenol. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 40, 836-842.

[29]   Nath, M., Saini, P.K. and Kumar, A. (2010) New di- and triorganotin(IV) complexes of tripodal Schiff base ligand containing three imidazole arms: Synthesis, structural characterization, anti-inflammatory activity and thermal studies. Journal of Organometallic Chemistry, 695, 1353- 1362. doi:10.1016/j.jorganchem.2010.02.009

[30]   Ferrero, J.R. (1971) Low-frequency Vibrations of Inorganic and Coordination Compounds, John Wiley & Sons, New York.

[31]   Singh, H.L. and Varshney, A.K. (2001) Synthesis and characterization of coordination compounds of organotin (IV) with nitrogen and sulphur donor ligands. Applied Organometallic Chemistry, 15, 762-768. doi:10.1002/aoc.234

[32]   Singh, H.L. (2010) Synthesis and characterization of tin (II) complexes of fluorinated Schiff bases derived from amino acids. Spectrochimica Acta Part A, 76, 253-258. doi:10.1016/j.saa.2010.03.029

[33]   Sandhu, G.K. and Verma, S.P. (1987) Triorganotin(IV) derivatives of five membered heterocyclic 2-carboxylic acids. Polyhedron, 6, 587-591. doi:10.1016/S0277-5387(00)81029-3

[34]   Szorcsik, A., Nagy, L., Sletten, J., Szalontai, G., Kamu, E., Fiore, T., Pellerito, L. and Kálmán, E. (2004) Preparation and structural studies on dibutyltin(IV) complexes with pyridine mono- and dicarboxylic acids. Journal of Organometallic Chemistry, 689, 1145-1154. doi:10.1016/j.jorganchem.2003.11.040

[35]   Ho, B.Y.K. and Zuckerman, J.J. (1973) Trialkyltin derivatives of amino acids and dipeptides. Inorganic Chemistry, 12, 1552-1561. doi:10.1021/ic50125a016

[36]   Sedaghat, T. and Jalilian, F. (2009) New adducts of diorganotin(IV) Chlorides with a new multifunctional Schiff base ligand: Synthesis and spectral properties. J. Iranian Chemical Society Synthesis, 6, 271-276.

[37]   Singh, H.L. and Varshney, A.K. (1999) Synthesis and spectral studies of organotin(IV) complexes with bifunctional tetradentate Schiff bases. Main Group Metal Chemistry, 22, 529-532. doi:10.1515/MGMC.1999.22.9.529

[38]   Pasto, D.J. (1969) Organic structure determination, Prentice Hall, London.

[39]   Nath, M. and Yadav, R. (1998) Studies of organotin(IV) derivatives of DL-methionine and L-asparagine. Bulletin of the Chemical Society of Japan, 71, 1355-1362. doi:10.1246/bcsj.71.1355

[40]   Joshi, A., Verma, S., Gaur, R. B. and Sharma, R. R. (2005) Di-n-butyltin(IV) Complexes Derived from Heterocyclic β-diketones and N-phthaloyl amino acids: Preparation, biological evaluation, structural elucidation based upon spectral [IR, NMR (1H, 13C, 19F and 119Sn)] studies. Bio- inorganic Chemistry and Applications, 3, 201-215. doi:10.1155/BCA.2005.201

[41]   Hole?ek, J., Nádvorník, M., Handlí?, K. and Ly?ka, A. (1986) 13C and 119Sn NMR spectra of Di-n-butyltin(IV) compounds. Journal of Organometallic Chemistry, 315, 299-308. doi:10.1016/0022-328X(86)80450-8

[42]   Jain, V. K., Mason, J., Saraswat, B.S. and Mehrotra, R.C. (1985) 15N, 13C and 119Sn NMR and other spectroscopic studies of 8-quinolinol, its O- and N-methyl derivatives, and chelate di- and tri-organotin(IV) complexes. Polyhedron, 4, 2089-2096. doi:10.1016/S0277-5387(00)86741-8

[43]   Pettinari, C., Pellei, M., Miliani, M., Cingolani, A., Cassetta, A., Barba, L., Pifferi, A. and Rivarola, E. (1998) Tin(IV) and organotin(IV) complexes containing mono or bidentate N-donor ligands: III.1 1-methylimidazole derivatives: synthesis, spectroscopic and structural characterization. Journal of Organometallic Chemistry, 553, 345-369. doi:10.1016/S0022-328X(97)00606-2

[44]   Chaturvedi, K.K. and Goyal, M. (1984) Antibacterial studies of 7-(α-substituted sulphonamido)methyl- and 7-(α-substituted sulphonamido)phenyl-8-hydroxyquino- lines. Journal of the Indian Chemical Society, 61, 175- 176.

[45]   Singh, H.L., Khungar, B., Tripaati, U.D. and Varshney, A.K. (2001) Spectral and antimicrobial studies of organotin(IV) complexes of bidentate schiff bases having nitrogen and sulphur donor systems. Main Group Metal Chemistry, 24, 5-12. doi:10.1515/MGMC.2001.24.1.5

 
 
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