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2-aminobenzotiyazolün karışık ligandlı metal kompleksleri ve biyolojik özellikleri hakkında literatür çalışması

Year 2018, Volume: 24 Issue: 7, 1360 - 1369, 28.12.2018

Abstract

2-Aminobenzotiyazol ile bazı organik bileşiklerin
[β-pikolin, γ-pikolin, isokinolin, asetilaseton, o-hidroksiasetofenon,
1,2-etilendiamin, piperazin, N,
N'-bis(4-antipirilmetil)piperazin,
N,N'-tetra(4-antipirilmetil)-1,2-diaminoetan, N,N'-bis(4-antipirilmetil)
piperazin, N, N'-tetra(4-antipirilmetil)-1,2-diaminoetan,
ftalamid,
malonamid, benzilaseton, tetrametilen sulfoksit, katekol, p-klorofenoksiasetik
asit, 7-oksobisiklo[2.2.1]
heptan-2,3-dikarboksilik asit,
2,2’-bipridin, 1.10-fenantrolin, propanoik asit, fenoksiasetik, 2-imino-3-allilbenzotiyazol,
sakarin, trifenilfosfin, trifloroasetik asit, adipik asit,
1,4-benzendikarboksilik asit, süksinik asit, formik
asit, pikrik asit, amino asit, p-formilfenoksiasetik asit ve
2,6-piridindikarboksilik asit] karışık ligandlı metal komplekslerinin (M = Mn,
Fe, Co, Ni, Cu, Zn, Ag, Au, Ru, Os, Ir, Pd, Rh, U, Eu ve Tb) yapıları ve
biyolojik özelliklerini anlatan çalışmalar literatürde gözlenmiştir.
Bu
bileşiklerde 2-aminobenzotiyazol metale tiyazol halkasının N ve/veya S ve/veya
animo grubundan bağlanmakta ya da tamamlayıcı iyon şeklinde yapıda yer
almaktadır. Bu
komplekslerinin antibakteriyel, antikanser,
antifungal, anti-inflamatuar, antitümör ve karbonik anhidraz inhibisyonu gibi biyolojik özellikleri bilinmektedir.

References

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  • Zhang-Gao L, Jian-Ping X, Huo-Yu R, Min Y. “One-pot synthesis of 2-aminobenzothiazoles using a new reagent of [bmim]br3 in [bmim]BF4”. Journal of Heterocyclic Chemistry, 43(1), 1123–1124, 2006.
  • Venkatesh P, Pandeya SN. “Synthesis, characterisation and anti-inflammatory activity of some 2-amino benzothiazole derivatives”. International Journal of ChemTech Research, 1(4), 1354-135, 2009.
  • Malik JK, Manvi FV, Nanjwade BK, Singh S. “Synthesis and screening of some new 2-amino substituted benzothiazole derivatives for antifungal activity”. Drug Invention Today, 1(1), 32-34, 2009.
  • İlkimen H. “2-Aminobenzotiyazol Türevlerinin 2,6-Pridindikarboksilik Asit ile Tuzlarının Hazırlanması, Bunların Geçiş Metal Komplekslerinin Sentezlenmesi, Yapılarının Aydınlatılması ve Kullanım Alanlarının Araştırılması”. Doktora Tezi, Dumlupınar Üniversitesi, Kütahya, Türkiye, 2013.
  • Chen ZF, Zhang M, Shi SM, Huang L, Liang H, Xu Q, Yu KB. “Synthesis, crystal structure and antibacterial activity of 2-aminobenzotiazole silver(I) nitrate”. Yingyong Huaxue, 22(7), 730-733, 2005.
  • Zhao B, Duan L, Wen W, Zhao YQ, Bin-Sheng Y. “Roles of Asp37 and Asp73 in the loop of N-terminal domain os ciliate uplotes octocarinatus centrin”. Chinese Journal of Inorganic Chemistry, 27, 245-250, 2011.
  • Marin AJ, Yubero N, Esteso G, Moreno A, de las Mulas JM, Morera L, Llanes D, Barbancho M, Garrido JJ. “Molecular characterization and expression analysis of the gene coding for the porcine β3 integrin subunit (CD61)”. Gene, 408(1-2), 9-17, 2008.
  • Gandhi N, Diamond ML, Meent VD, Huijbregts MAJ, Peijnenburg WJGM, Guinee J. “New method for calculating comparative toxicity potential of cationic metals in freshwater: application to copper, nickel, and zinc”. Environmental Science and Technology, 44(13), 5195-5201, 2010.
  • Fang G, Xu M, Zeng F, Wu S. “β-Cyclodextrin as the vehicle for forming ratiometric mercury ion sensor usable in aqueous media, biological fluids and live cells”. Langmuir, 26(22), 17764-17771, 2010.
  • Shukla SN, Gaur P, Kaur H, Prasad M, Mehrotra R, “Srivastava RS. Synthesis, spectroscopic characterization and antibacterial sensitivity of some chloro dimethylsulfoxide/tetramethylene sulfoxide ruthenium (II) and ruthenium (III) complexes with 2-aminobenzothiazole”. Journal of Coordination Chemistry, 61(3), 441-449, 2008.
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  • Gu HB, Wang L, Zhao CQ, Gong Y, Chen WY. “Synthesis, crystal structure and antimicrobial activity of a ternary copper(II) complex with para-formylphenoxyacetic acid and 2-amino benzothiazole”. Wuji Huaxue Xuebao, 25(8), 1464-1469, 2009.
  • Neelakantan MA, Mariappan SS, Dharmaraja J, Muthukumaran K. “pH metric, spectroscopic and thermodynamic study of complexation behavior of 2-aminobenzothiazole with Ni (II) in presence of amino acids”. Acta Chimica Slovenica, 57(1), 198-205, 2010.
  • Gao EJ, Liu L, Zhu MC, Huang Y, Guan F, Gao XN, Zhang M, Wang L, Zhang WZ, Sun YG. “Synthesis, characterization, interaction with DNA and cytotoxic effect in vitro of new mono- and dinuclear Pd(II) and Pt(II) complexes with benzo[d]thiazol-2-amine as the primary ligand”. Inorganic Chemistry (Washington, DC, United States), 50(11), 4732-4741, 2011.
  • İlkimen H, Yenikaya C, Sarı M, Bülbül M, Tunca E, Dal H. “Synthesis and characterization of a proton transfer salt between 2,6-pyridinedicarboxylic acid and 2-aminobenzothiazole, and its complexes and their inhibition studies on carbonic anhydrase isoenzymes”. Journal of Enzyme Inhibition Medicinal Chemistry, 29(3), 353-361, 2014.
  • Shabana AA, Butler IS, Gilson DFR, Jean-Claude BJ, Mouhri ZS, Mostafa MM, Mostafa SI. “Synthesis, characterization, anticancer activity and DNA interaction studies of new 2-aminobenzothiazole Complexes; Crystal structure and DFT calculations of [Ag(Habt)2]ClO4 Dedicated to Mirto Mozzon”. Inorganica Chimica Acta, 423(PB), 242-255, 2014.
  • Chen XY, Femia FJ, Babich JW, Zubieta J. “Spectroscopic and structural studies of complexes of the fac-[Re(N∩N)(CO)3L]n+ type (N∩N= 2-(2-pyridyl)benzothiazole; L= Cl, Br, CF3SO3 −, CH3CN)”. Inorganic Chimica Acta, 314(1-2), 91-96, 2001.
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  • Maurya RC, Mishra DD, Trivedi PK, Mukherjee S, Shukla P. “Synthesis and physicochemical studies of some novel pentacoordinated derivatives of zinc(II)-bis(acetylacetone) and -bis(acetoacetanilide chelates containing heterocyclic nitrogen donors”. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 21(8), 1219-29, 1991.
  • Maurya RC, Pillai S, Singh T, Singh H, Shukla B. “Biochemically relevant complexes of copper: Synthesis, magnetic and spectral studies of some mixed-ligand chelates of bis(o-hydroxyacetophenonato)copper(II) with benzothiazole and related ligands”. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 28(7), 1053-1064, 1998.
  • Sieron L, Bukowska-Strzyzewska M. “cis-Bis(2-amino-1,3-benzothiazole-N3)bis(formato-O,O')copper(II)”. Acta Crystallographica, Section C: Crystal Structure Communications, 55(2), 167-169, 1999.
  • Maurya RC, Sharma P. “Synthesis, magnetic and spectral studies of Co(II) picrate complexes with heterocyclic nitrogen donors”. Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry, 38A(5), 509-513, 1999.
  • Maurya RC, Sharma P, Roy S. “Synthesis and characterization of some mixed-ligand picrate complexes of nickel(II) involving heterocyclic nitrogen donors”. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33(4), 683-698, 2003.
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A review on biological properties and mixed ligand metal complexes of 2-aminobenzothiazole

Year 2018, Volume: 24 Issue: 7, 1360 - 1369, 28.12.2018

Abstract

The
studies about the structures and biological properties of the mixed ligand
metal complexes (Mn+, M = Mn, Fe, Co, Ni, Cu, Zn, Ag, Au, Ru, Os, Ir, Pd, Rh,
U, Eu, and Tb) of the 2- aminobenzothiazole and some organic compounds
(β-picoline, γ-picoline isopicoline, acetylaceton, o-hydroxyacetophenone, 1,2-ethylenediamine, piperazine, N,N'-bis(4-antipyrylmethyl) piperazine,
N,N'-tetra(4-antipyrylmethyl)-1,2-diaminoethane, phtalamide, malonimide,
benzylacetone, tetramethylenesulphoxide, catechol, p-chlorophenoxyacetic acid, 7-oxobicyclo[2.2.1]-heptan-2,3-dicarboxylic acid, 2,2’-bipyridine, 1,10-phenanthroline, propionic acid, phenoxyacetic acid,
2-amino-3-allylbenzothiazole, saccharine, triphenylphosphine, trichloroacetic
acid, adipic acid, 1,4-benzenedicarboxylic acid,  succinic acid, formic acid, picric acid,
amino acid, p-formylphenoxyacetik acid and 2,6-pyridinedicarboxylic acid) have been observed in the literature. In these
compounds, 2-aminobenzothiazole connected to the metal from N or S or amine
group of thiazole ring or take part in the structure as the complementary form.
Some biological properties such as antimicrobial, anticancer, antifungal,
anti-inflammatory, antitumor and inhibition of carbonic anhydrase of these
complexes are well-known.

References

  • Towns AD. “Developments in azo disperse dyes derived from heterocyclic diazo components”. Dyes Pigments, 42(1), 3-28, 1999.
  • Zhang-Gao L, Jian-Ping X, Huo-Yu R, Min Y. “One-pot synthesis of 2-aminobenzothiazoles using a new reagent of [bmim]br3 in [bmim]BF4”. Journal of Heterocyclic Chemistry, 43(1), 1123–1124, 2006.
  • Venkatesh P, Pandeya SN. “Synthesis, characterisation and anti-inflammatory activity of some 2-amino benzothiazole derivatives”. International Journal of ChemTech Research, 1(4), 1354-135, 2009.
  • Malik JK, Manvi FV, Nanjwade BK, Singh S. “Synthesis and screening of some new 2-amino substituted benzothiazole derivatives for antifungal activity”. Drug Invention Today, 1(1), 32-34, 2009.
  • İlkimen H. “2-Aminobenzotiyazol Türevlerinin 2,6-Pridindikarboksilik Asit ile Tuzlarının Hazırlanması, Bunların Geçiş Metal Komplekslerinin Sentezlenmesi, Yapılarının Aydınlatılması ve Kullanım Alanlarının Araştırılması”. Doktora Tezi, Dumlupınar Üniversitesi, Kütahya, Türkiye, 2013.
  • Chen ZF, Zhang M, Shi SM, Huang L, Liang H, Xu Q, Yu KB. “Synthesis, crystal structure and antibacterial activity of 2-aminobenzotiazole silver(I) nitrate”. Yingyong Huaxue, 22(7), 730-733, 2005.
  • Zhao B, Duan L, Wen W, Zhao YQ, Bin-Sheng Y. “Roles of Asp37 and Asp73 in the loop of N-terminal domain os ciliate uplotes octocarinatus centrin”. Chinese Journal of Inorganic Chemistry, 27, 245-250, 2011.
  • Marin AJ, Yubero N, Esteso G, Moreno A, de las Mulas JM, Morera L, Llanes D, Barbancho M, Garrido JJ. “Molecular characterization and expression analysis of the gene coding for the porcine β3 integrin subunit (CD61)”. Gene, 408(1-2), 9-17, 2008.
  • Gandhi N, Diamond ML, Meent VD, Huijbregts MAJ, Peijnenburg WJGM, Guinee J. “New method for calculating comparative toxicity potential of cationic metals in freshwater: application to copper, nickel, and zinc”. Environmental Science and Technology, 44(13), 5195-5201, 2010.
  • Fang G, Xu M, Zeng F, Wu S. “β-Cyclodextrin as the vehicle for forming ratiometric mercury ion sensor usable in aqueous media, biological fluids and live cells”. Langmuir, 26(22), 17764-17771, 2010.
  • Shukla SN, Gaur P, Kaur H, Prasad M, Mehrotra R, “Srivastava RS. Synthesis, spectroscopic characterization and antibacterial sensitivity of some chloro dimethylsulfoxide/tetramethylene sulfoxide ruthenium (II) and ruthenium (III) complexes with 2-aminobenzothiazole”. Journal of Coordination Chemistry, 61(3), 441-449, 2008.
  • Jain C, Nagar M, Seth G. “Biological important Co(II) ternary complexes of 2-substituted benzazoles and amino acids”. Journal of Chemical and Pharmaceutical Research, 5(11), 501-505, 2013.
  • Gu HB, Wang L, Zhao CQ, Gong Y, Chen WY. “Synthesis, crystal structure and antimicrobial activity of a ternary copper(II) complex with para-formylphenoxyacetic acid and 2-amino benzothiazole”. Wuji Huaxue Xuebao, 25(8), 1464-1469, 2009.
  • Neelakantan MA, Mariappan SS, Dharmaraja J, Muthukumaran K. “pH metric, spectroscopic and thermodynamic study of complexation behavior of 2-aminobenzothiazole with Ni (II) in presence of amino acids”. Acta Chimica Slovenica, 57(1), 198-205, 2010.
  • Gao EJ, Liu L, Zhu MC, Huang Y, Guan F, Gao XN, Zhang M, Wang L, Zhang WZ, Sun YG. “Synthesis, characterization, interaction with DNA and cytotoxic effect in vitro of new mono- and dinuclear Pd(II) and Pt(II) complexes with benzo[d]thiazol-2-amine as the primary ligand”. Inorganic Chemistry (Washington, DC, United States), 50(11), 4732-4741, 2011.
  • İlkimen H, Yenikaya C, Sarı M, Bülbül M, Tunca E, Dal H. “Synthesis and characterization of a proton transfer salt between 2,6-pyridinedicarboxylic acid and 2-aminobenzothiazole, and its complexes and their inhibition studies on carbonic anhydrase isoenzymes”. Journal of Enzyme Inhibition Medicinal Chemistry, 29(3), 353-361, 2014.
  • Shabana AA, Butler IS, Gilson DFR, Jean-Claude BJ, Mouhri ZS, Mostafa MM, Mostafa SI. “Synthesis, characterization, anticancer activity and DNA interaction studies of new 2-aminobenzothiazole Complexes; Crystal structure and DFT calculations of [Ag(Habt)2]ClO4 Dedicated to Mirto Mozzon”. Inorganica Chimica Acta, 423(PB), 242-255, 2014.
  • Chen XY, Femia FJ, Babich JW, Zubieta J. “Spectroscopic and structural studies of complexes of the fac-[Re(N∩N)(CO)3L]n+ type (N∩N= 2-(2-pyridyl)benzothiazole; L= Cl, Br, CF3SO3 −, CH3CN)”. Inorganic Chimica Acta, 314(1-2), 91-96, 2001.
  • Hadjikakou SK, Kubicki M. “Synthesis, characterisation and study of mercury(II) chloride complexes with triphenylphosphine and heterocyclic thiones. The crystal structures of [(benzothiazole-2-thionato)(benzothiazole-2-thione) (bis-triphenyl phosphine)chloromercury(II)] and [(μ2-dichloro){(bis-pyrimidine-2-thionato)mercury(II)}{(bis-triphenylphosphine)mercury(II)}] at 100 K”. Polyhedron, 19(20-21), 2231-2236, 2000.
  • Hofmann AW. “Zur kenntniss des o-amidophenylmercaptans”. Chemische Berichte, 20(1), 1788-1797, 1887.
  • Hugerschoff H. “Einwirkung von halogenen auf thioharnstoffe”. Berichte der Deutschen Chemischen Gesellschaft, 34(2), 3130-3135, 1901.
  • Hugerschoff H. “Einwirkung von brom auf aromatische thioharnstoffe”. Berichte der Deutschen Chemischen Gesellschaft, 36(3), 3121-3134, 1903.
  • Mahapatra SC, Rao DVR. “Mixed ligand thiocyanato complexes of cobalt(II)-coordination number six and eight”. Journal of the Indian Chemical Society, 57(3), 262-264, 1980.
  • Maurya RC, Mishra DD, Trivedi PK, Mukherjee S, Shukla P. “Synthesis and physicochemical studies of some novel pentacoordinated derivatives of zinc(II)-bis(acetylacetone) and -bis(acetoacetanilide chelates containing heterocyclic nitrogen donors”. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 21(8), 1219-29, 1991.
  • Maurya RC, Pillai S, Singh T, Singh H, Shukla B. “Biochemically relevant complexes of copper: Synthesis, magnetic and spectral studies of some mixed-ligand chelates of bis(o-hydroxyacetophenonato)copper(II) with benzothiazole and related ligands”. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 28(7), 1053-1064, 1998.
  • Sieron L, Bukowska-Strzyzewska M. “cis-Bis(2-amino-1,3-benzothiazole-N3)bis(formato-O,O')copper(II)”. Acta Crystallographica, Section C: Crystal Structure Communications, 55(2), 167-169, 1999.
  • Maurya RC, Sharma P. “Synthesis, magnetic and spectral studies of Co(II) picrate complexes with heterocyclic nitrogen donors”. Indian Journal of Chemistry, Section A: Inorganic, Bio-inorganic, Physical, Theoretical & Analytical Chemistry, 38A(5), 509-513, 1999.
  • Maurya RC, Sharma P, Roy S. “Synthesis and characterization of some mixed-ligand picrate complexes of nickel(II) involving heterocyclic nitrogen donors”. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 33(4), 683-698, 2003.
  • Labadi I, Tudose R, Fejer I, Jori Z, Costisor O. “Thermal behaviour of complexes of antipyrine derivatives”. Journal of Thermal Analysis and Calorimetry, 56(2), 553-559, 1999.
  • Sieron L, Bukowska-Strzyzewska M. “Bis(μ-succinato-O,O':O",O"')bis[bis(2-amino-1,3-benzothiazole-N3)copper(II)]”. Acta Crystallographica, Section C: Crystal Structure Communications, C56(1), 19-21, 2000.
  • Costisor O, Mracec M, Jori Z, Labadi I, Linert W. “Mixed-ligand complexes of Co(II) and Cu(II) with pyrazolonic Mannich bases and 2-aminobenzothiazole”. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 30(8), 1489-1504, 2000.
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There are 54 citations in total.

Details

Primary Language Turkish
Subjects Engineering
Journal Section Review Article
Authors

Halil İlkimen 0000-0003-1747-159X

Publication Date December 28, 2018
Published in Issue Year 2018 Volume: 24 Issue: 7

Cite

APA İlkimen, H. (2018). 2-aminobenzotiyazolün karışık ligandlı metal kompleksleri ve biyolojik özellikleri hakkında literatür çalışması. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, 24(7), 1360-1369.
AMA İlkimen H. 2-aminobenzotiyazolün karışık ligandlı metal kompleksleri ve biyolojik özellikleri hakkında literatür çalışması. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. December 2018;24(7):1360-1369.
Chicago İlkimen, Halil. “2-aminobenzotiyazolün karışık Ligandlı Metal Kompleksleri Ve Biyolojik özellikleri hakkında literatür çalışması”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 24, no. 7 (December 2018): 1360-69.
EndNote İlkimen H (December 1, 2018) 2-aminobenzotiyazolün karışık ligandlı metal kompleksleri ve biyolojik özellikleri hakkında literatür çalışması. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 24 7 1360–1369.
IEEE H. İlkimen, “2-aminobenzotiyazolün karışık ligandlı metal kompleksleri ve biyolojik özellikleri hakkında literatür çalışması”, Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, vol. 24, no. 7, pp. 1360–1369, 2018.
ISNAD İlkimen, Halil. “2-aminobenzotiyazolün karışık Ligandlı Metal Kompleksleri Ve Biyolojik özellikleri hakkında literatür çalışması”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi 24/7 (December 2018), 1360-1369.
JAMA İlkimen H. 2-aminobenzotiyazolün karışık ligandlı metal kompleksleri ve biyolojik özellikleri hakkında literatür çalışması. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. 2018;24:1360–1369.
MLA İlkimen, Halil. “2-aminobenzotiyazolün karışık Ligandlı Metal Kompleksleri Ve Biyolojik özellikleri hakkında literatür çalışması”. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi, vol. 24, no. 7, 2018, pp. 1360-9.
Vancouver İlkimen H. 2-aminobenzotiyazolün karışık ligandlı metal kompleksleri ve biyolojik özellikleri hakkında literatür çalışması. Pamukkale Üniversitesi Mühendislik Bilimleri Dergisi. 2018;24(7):1360-9.

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