Di- and triorganotin(IV) esters of 3,4-methylenedioxyphenylpropenoic acid: Synthesis, spectroscopic characterization and biological screening for antimicrobial, cytotoxic and antitumor activities

Chemical Biology and Drug Design

Volumn 71, Issue 6, 2008, Pages 568-576

  Ahmad, Muhammad Sheeraz ^a   Hussain, Mukhtiar ^a   Hanif, Muhammad ^a   Ali, Saqib ^a   Qayyum, Mazhar ^b   Mirza, Bushra ^a  

^a QUAID I AZAM UNIVERSITY   (Pakistan)

^b PMAS ARID AGRICULTURE UNIVERSITY   (Pakistan)

Author keywords

Antibacterial; Antifungal; Antitumor; Cytotoxicity; Mass spectrometry; Multinuclear NMR; Organotin; Pathogenic

Indexed keywords

3,4 METHYLENEDIOXYPHENYLPROPENOIC ACID DERIVATIVE; CEFIXIME; DI N BUTYLTIN BIS[3 (3,4 METHYLENEDIOXYPHENYL)PROPENOATE]; DI N OCTYLTIN BIS[3 (3,4 METHYLENEDIOXYPHENYL)PROPENOATE]; DIMETHYLTIN BIS[3 (3,4 METHYLENEDIOXYPHENYL)PROPENOATE]; LIGAND; METAL; ORGANOTIN COMPOUND; ROXITHROMYCIN; TRICYCLOHEXYLTIN [3 (3,4 METHYLENEDIOXYPHENYL)PROPENOATE];

ANALYTIC METHOD; ANTIFUNGAL ACTIVITY; ANTIMICROBIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASSAY; BACTERIAL STRAIN; BRINE SHRIMP LETHALITY ASSAY; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CONTROLLED STUDY; CYTOTOXICITY; DRUG SCREENING; DRUG SYNTHESIS; FUNGAL STRAIN; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; TIN 119 NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ANIMALS; ANTI-INFECTIVE AGENTS; ANTINEOPLASTIC AGENTS; ARTEMIA; DRUG EVALUATION, PRECLINICAL; ESTERS; FUNGI; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; MAGNETIC RESONANCE SPECTROSCOPY; ORGANOTIN COMPOUNDS; PLANT TUMORS; SPECTRUM ANALYSIS;

ARTEMIA; BACTERIA (MICROORGANISMS); NEGIBACTERIA; POSIBACTERIA; SOLANUM TUBEROSUM;

EID: 43949104816     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2008.00668.x     Document Type: Article

References (25)

1. Bonire J.J., Ayoko G.A., Olurinola P.F., Ehinmidu J.O., Jalil N.S.N., Omachi A.A. (1998) Synthesis and antifungal activity of some organotin(IV) carboxylates. Met Based Drugs 5 : 233 236.
2. Chohan Z.H., Supuran C.T. (2005) In-vitro antibacterial and cytotoxic activity of cobalt(II), copper(II), nickel(II) and zinc(II) complexes of the antibiotic drug cephalothin (Keflin). J Enzyme Inhib Med Chem 20 : 463 467.
3. Maqsood Z.T., Khalid K.M., Ashiq U., Jamal R.A., Chohan Z.H., Mahroof-Tahir M., Supuran C.T. (2006) Oxovanadium(IV) complexesof hydrazides: Potential antifungal agents. J Enzyme Inhib Med Chem 21 : 37 40.
4. Rehman S.U., Chohan Z.H., Gulnaz F., Supuran C.T. (2005) In-vitro antibacterial, antifungal and cytotoxic activities of some coumarins and their metal complexes. J Enzyme Inhib Med Chem 20 : 333 337.
5. Tabassum S., Pettinari C. (2006) Chemical and biotechnological developments in organotin cancer chemotherapy. J Organomet Chem 691 : 1761 1766.
6. Gielen M., Biesemans M., de-Vos D., Willem R. (2000) Synthesis, characterization and in vitro antitumor activity of di- and triorganotin derivatives of polyoxa- and biologically relevant carboxylic acids. J Inorg Biochem 79 : 139 145.
7. Chandrasekhar V., Nagendran S., Baskar V. (2002) Organotin assemblies containing Sn-O bonds. Coord Chem Rev 1 : 235 240.
8. Nath M., Pokharia S., Yadav R. (2001) Organotin(IV) complexes of amino acids and peptides. Coord Chem Rev 99 : 215 220.
9. Hanif M., Hussain M., Ali S., Bhatti M.H., Ahmad M.S., Mirza B., Evans H.S. (2007) Synthesis, spectroscopic investigation, crystal structure, and biological screening, including antitumor activity, of organotin(IV) derivatives of Piperonylic acid. Turk J Chem 31 : 349 361.
10. Ahmed M.S., Hussain M., Hanif M., Ali S., 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.
11. 119Sn NMR, IR, mass, thermal and biological studies of organotin(IV) derivatives of 4-p-(Chlorophenyl)-2-phynyl-5-thiazole-acetic acid. Synth React Inorg Met-Org Chem 32 : 1373 1392.
12. Parvez M., Ahmad S., Ali S., Bhatti M.H., Mazhar M. (2004) Polymeric [2-(N-maleoyl)-2-methyl-propionato] trimethyltin(IV). Acta Crystallogr E 60 : m554 m556.
13. Rehman A., Choudhary M.I., Thomsen W.J. (2001) Bioassay Techniques for Drug Development. Amsterdam : Harwood Academic Publishers p. 9 25.
14. Mayer B.N., Ferrigni N.R., Putnam J.E., Jacobson L.B., Nichols D.E., Mclaughlin J.L. (1982) Brine shrimp: a convenient general bioassay for active plant constituents. Planta Med 45 : 31 34.
15. Inayatullah S., Irum R., Rehman A., Chaudhary M.F., Mirza B. (2007) Biological evaluation of some selected plant species of Pakistan. Pharm Biol 45 : 397 403.
16. Parvez M., Ahmad S., Ali S., Bhatti M.H., Mazhar M. (2004) catena-Poly[[trimethyltin(IV)]-μ-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl) -3-phenylpropionato-κ2O:O′]. Acta Crystallogr E 60 : m190 m192.
17. Parvez M., Ali S., Ahmed S., Bhatti M.H., Mazhar M. (2002) catena-Poly[[tri-n-butyltin]-l-N-(1-naphthyl)maleamato]. Acta Crystallogr C 58 : m334 m335.
18. /-dithiocarbamato) Pd(II). J Organomet Chem 692 : 3019 3026.
19. 119mSn Mössbauer, infrared and mass spectrometric studies of organotin carboxylates of 2-(2,3-dimethylphenyl)aminobenzoic acid and their effect on microorganisms. Synth React Inorg Met-Org Chem 27 : 863 885.
20. 119Sn NMR spectra of some four- and five-coordinate tri-n-butyltin(IV) compounds. J Organomet Chem 275 : 43 51.
21. Kalinowski H.O., Berger S., Braun S. (1988) Carbon NMR Spectroscopy. Chichester, UK : John Wiley & Sons p. 313.
22. Rehman S.U., Ali S., Badshah A., Malik A., Ahmed E., Jin G.X., Tiekink E.R.T. (2004) Di- and tri-organotin(IV) derivatives of (Z)-3-(4-nitrophenyl)-2- phenyl-2-propenoic acid: spectroscopic characterization and biocidal studies. Crystal structure analysis of tetrameric tri-nbutyltin(IV) (Z)-3-(4-nitrophenyl) -2-phenyl-2-propenoate. Appl Organomet Chem 18 : 401 408.
23. Shahzadi S., Ali S., Bhatti M.H., Fettouhi M., Athar M. (2006) Chloro-diorganotin(IV) complexes of 4-methyl-1-piperidine carbodithioic acid: Synthesis, X-ray crystal structures, spectral properties and antimicrobial studies. J Organomet Chem 691 : 1797 1802.
24. Shahid K., Shahzadi S., Ali S., Mazhar M. (2006) Synthesis, spectroscopic studies and biological applications of organotin(IV) derivatives of 3-[N-(4-Nitrophenyl) amido]propenoic acid and 3-[N-(4-Nitrophenyl)-amido] propanoic acid. Bull Korean Chem Soc 27 : 44 52.
25. Bacchi A., Carcelli M., Pelagatti P., Pellizi G., Rodriguez-Aruguelles M.C., Rogolino D., Solinas C., Zani F. (2005) Antimicrobial and mutagenic properties of organotin(IV) complexes with isatin and N-alkylisatin bisthiocarbonohydrazones. J Inorg Biochem 99 : 397 408.