Synthesis and biological activity of new cycloalkylthiophene-Schiff bases and their Cr(III) and Zn(II) complexes

Medicinal Chemistry Research

Volumn 19, Issue 6, 2010, Pages 576-588

  Altundas, Aliye ^a   Sarı, Nurşen ^a   Colak, Naki ^b   Ögütcü, Hatice ^c  

^a GAZI UNIVERSITY   (Turkey)

^b HITIT UNIVERSITY   (Turkey)

^c Refik Saydam Hygiene Center   (Turkey)

Author keywords

Antimicrobial activity; Cycloalkylthiophenes; Drug; Gewald methods; Schiff bases; Sulfur

Indexed keywords

AMOXICILLIN; AMPICILLIN; CHLORAMPHENICOL; CHLOROAMPHENICOL; CHROMIUM; ETHYL 2 [(1 HYDROXYNAPHTALEN 2 YL)METHYLENEAMINO] 5,6,7,8 TETRAHYDRO 4H CYCLOHEPTA[B]THIOPHENE 3 CARBOXYLATE; ETHYL 2 [(1 HYDROXYNAPHTHALEN 2 YL)METHYLENEAMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXYLATE; ETHYL 2 [(1 HYDROXYNAPHTHALEN 2 YL)METHYLENEAMINO] 5,6 DIHYDRO 4H CYCLOPENTA[B]THIOPEHENE 3 CARBOXYLATE; KANAMYCIN; METAL COMPLEX; NYSTATIN; OFLOXACIN; SCHIFF BASE; SULFAMETHOXAZOLE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG; ZINC DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; BIOLOGICAL ACTIVITY; BRUCELLA ABORTUS; CANDIDA ALBICANS; COMPLEX FORMATION; DRUG SYNTHESIS; ESCHERICHIA COLI; LIQUID CHROMATOGRAPHY; LISTERIA MONOCYTOGENES; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PROTEUS; PSEUDOMONAS PUTIDA; SALMONELLA TYPHI; SHIGELLA BOYDII; STAPHYLOCOCCUS AUREUS; ULTRAVIOLET SPECTROPHOTOMETRY; YEAST;

EID: 77956463372     PISSN: 10542523     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00044-009-9214-8     Document Type: Article

References (32)

1. AbouEl-Enein SA, El-Saied FA, Kasher TI, El-Wardany AH (2007) Synthesis and characterization of iron(III), manganese(II), cobalt(II), nickel(II), copper(II) and zinc(II) complexes of salicylidene-Nanilinoacetohydrazone (H2L1) and 2-hydroxy-1-naphthylidene-N-anilinoacetohydrazone (H2L2). Spectrochim Acta A Mol Biomol Spectrosc 67:737-743. doi:10.1016/j.saa.2006.07.052
2. Angelici RJ (1990) Structural aspects of thiophene coordination in transition metal complexes. Coord Chem Rev 105:61-76. doi:10.1016/0010-8545(90) 80018-O
3. Arslan S, Logoglu E,Öktemer A (2006) Antimicrobial activity studies on some piperidine and pyrrolidine substituted halogenobenzene derivatives. J Enzyme Inhib Med Chem 21:211-214. doi:10.1080/ 14756360600563063
4. Avaji PG, Patil SA, Badami S (2008) Transition metal complexes of 13- and 14-membered N2O2 macrocycles: synthesis and characterization. Trans Met Chem (Weinh) 33:275-283. doi:10.1007/ s11243-007-9041-z
5. Basak S, Mondal A, Chopra D, Rajak KK (2007) Synthesis and structural characterisation of new Re(III) complexes using aldimines of a-amino acids as coligands. Polyhedron 26:3465-3470. doi:10.1016/ j.poly.2007.03.036
6. Bermingham A, Derrick JP (2002) The folic acid biosynthesis pathway in bacteria evaluation of potential for antibacterial drug discovery. Bioessays 24:637-648. doi:10.1002/bies.10114
7. Burlov AS, Shepelenko EN, Vasil'chenko IS, Antsyshkina AS, Sadkov GG, Matuev PV, Nikolaevskii SA, Borodkin GS, Sergienko VS, Bren' VA, Garnovskii AD (2006) Metal chelates with salicylidene-3-carboethoxy-4,5-dimethylthiophene derivatives as azomethine ligands of a new type. Russ J Coord Chem 32:879-884. doi:10.1134/S1070328406120049
8. Cotton FA, Wilkinson G (1972) Advanced inorganic chemistry, 3rd edn. Wiley, New York
9. Farkas E, Bátka D, Csóka H, Nagy NV (2007) Interaction of imidazole containing hydroxamic acids with Fe(III): hydroxamate versus imidazole coordination of the ligands Bioinorg Chem Appl 96536:1-8
10. Gewald K, Schinke E, Böttcher H (1966) Heterocyclen aus CH-aciden Nitrilen, VIII. 2-Amino-thiophene aus methylenaktiven Nitrilen. Carbonylverbindungen Schwefel Chemische Ber 99:94-100. doi:10.1002/cber. 19660990116
11. Hallas G, Choi J-H (1999) Synthesis and properties of novel aziridinyl azo dyes from 2-aminothiophenes- Part 1: synthesis and spectral properties. Dyes Pigments 40:99-117. doi:10.1016/S0143-7208 (98)00034-35
12. Halling SM, Peterson Burch BD, Bricker BJ, Zuerner RL, Qing Z, Li L, Kapur V, Alt DP, Olsen SC (2005) Completion of the genome sequence of Brucella abortus and comparison to the highly similar genomes of Brucella melitensis and Brucella suis. J Bacteriol 187:2715-2726. doi: 10.1128/JB.187.8.2715-2726.2005
13. Herrera V, Muñoz B, Landaeta V, Canudas N (2007) Homogeneous hydrogenation of imines catalyzed by rhodium and iridium complexes. Kinetics and mechanism of the hydrogenation of N-(b-naphthyl methylene) aniline using [Ir(COD)(PPh3)2]PF6 as catalyst precursor. J Mol Cataly A 174:141-149
14. Jain M, Singh RV (2006) Synthesis, characterization and biotoxicity of NN donor sulphonamide imine silicon (IV) complexes. Bioinorg Chem Appl 2006:10. doi:10.1155/BCA/2006/13743
15. Joseph J, Mehta BH (2007) Synthesis, characterization, and thermal analysis of transition metal complexes of polydentate ONO donor Schiff base ligand. Russ J Coord Chem 53:124-129. doi: 10.1134/S1070328407020091
16. Kurtoǧlu M, Ispir E, Kurtoǧlu N, Serin S (2008) Novel vic-dioximes: synthesis, complexation with transition metal ions, spectral studies and biological activity. Dyes Pigments 77:75-80. doi: 10.1016/j.dyepig.2007.03.010
17. Logoglu E, Arslan S, Öktemer A, Şakiyan I (2006) Biological activities of some natural compounds from Sideritis sipylea Boiss. Phytother Res 20:294-297. doi:10.1002/ptr.1855
18. Lippard SJ, Berg JM (1994) Principles of bioinorganic chemistry. University Science Books, Mill Valley, CA
19. Modi JD, Sabnis SS, Deliwala CV (1970) Potential anticancer agents. III. Schiff bases from benzaldehyde nitrogen mustards and aminophenylthiazoles. J Med Chem 13:935-941. doi:10.1021/jm00299a031
20. Mohanan K, Devi SN, Murukan B (2006) Complexes of copper(II) with 2-(N-salicylideneamino)-3- carboxyethyl-4,5,6,7-tetrahydrobenzo[b]thiophene containing different counter anions. Synt React Inorg Met Org Chem 36:441-449
21. Murukan B, Mohanan K (2007) Synthesis, characterization and antibacterial properties of some trivalent metal complexes with [(2-hydroxy-1-naphthaldehyde) -3-isatin]-bishydrazone. J Enzym Inhib Med Chem 22:65-70
22. Nakamoto K (1986) Infrared and Raman spectra of inorganic and coordination compounds, 4th edn. Wiley, New York
23. Nawwar GAM, Shafik NA (1995) Synthesis of 2-substituted benzothiazoles containing amino acid, imino or heteroaryl moieties with anticipated fungicidal activity. Collect Czech Chem Commun 60:2200-2208. doi:10.1135/cccc19952200
24. Peet NP, Sunder S, Barbuch RJ, Vinogradoff AP (1986) Mechanistic observations in the Gewald syntheses of 2-aminothiophenes. J Heterocycl Chem 23:129-134. doi:10.1002/jhet.5570230126
25. Sabnis RW, Rangnekar DW, Sonawane ND (1999) 2-Aminothiophenes by the Gewald reaction. J Heterocycl Chem 36:333-346. doi:10.1002/jhet.5570360203
26. Sari N, Gürkan P (2004) Some novel amino acid-Schiff bases and their complexes synthesis, characterization, solid state conductivity behaviors and potentiometric Studies. Z Naturforsch [B] 59b:692-697
27. Sari N, Gürkan P, Arslan S (2003) Synthesis, potentiometric and antimicrobial activity studies on 2-pyridinilidene-DL-amino acids and their complexes. Trans Met Chem (Weinh) 28:468-474. doi: 10.1023/A:1023685719951
28. Sari N, Nartop D, Karci F, Dişli A (2008) Novel hydrazone derivates and their tetracoordinated metal complexes. Asian J Chem 20:1975-1985
29. Silverstein RM, Bassler GC, Morrill TC (1981) Spectrophotometric identification of organic compounds, 4th edn. Wiley, New York
30. Singh K, Singh DP, Barwa MS, Tyagi P, Mirza Y (2006) Antibacterial Co(II), Ni(II), Cu(II) and Zn(II) complexes of Schiff bases derived from fluorobenzaldehyde and triazoles. J Enzyme Inhib Med Chem 21:557-562. doi:10.1080/14756360600642131
31. Takeuchi T, Böttcher A, Quezada CM, Meade TJ, Gray HB (1999) Inhibition of thermolysin and human a-thrombin by cobalt(III) Schiff base complexes. Bioorg Med Chem 5:815-819. doi: 10.1016/S0968-0896(98)00272-7
32. Zhikuan L, Twieg RJ, Huang SD (2003) Copper-catalyzed amination of aromatic halides with 2-N,Ndimethylaminoethanol as solvent. Tetrahedron Lett 44:6289-6292. doi:10.1016/S0040-4039 (03)01536-1543