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2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ ve BİYOLOJİK ÖZELLİKLERİ

Yıl 2021, Sayı: 004, 19 - 28, 30.12.2021

Öz

2-Aminobenzimidazol ve türevlerin, antibakteriyel, antikanser, antiviral, antiinflamatuvar, antiproliferatif, antifungal, antelmintik ve antihistaminik özelliklere sahip olduğu çalışmalar literatürde bulunmaktadır. 2-Aminobenzimidazol ve türevleri yapısında üç adet azot atomlarından dolayı metal iyonlarına bir ve iki dişli olarak bağlanmaktadır. 2-Aminobenzimidazol ve türevlerinin basit metal kompleksleri sentezlenmiştir. Ayrıca trimesik asit, tereftalik asit, isoftalik asit, glutarik asit, 2,6-piridindikarboksilik asit, 4-hidroksi-2,6-piridindikarboksilik asit, krotonik asit, okzalik asit, pirazin-2-karboksilik asit, p-simen, sakarin, disiyanamit, N-salisiliden-2-hidroksianilin, asetoasetanilit, o-asetoasetotoluidit, o-asetoasetanisidit, dehidroasetik asit, 4,4’-bipiridin, bis-(salisilaldehit)fenilendiimin, N-(dehidroasetik asit)-tiyosemikarbazit, N-(dehidroasetik asit)-4-metil-3-tiyosemikarbazit, 4,5-dimetil-N,N-bis(piridin-2-yil-metilen)benzen-1,2-diimin, N-(dehidroasetik asit)-4- fenilsemikarbazit ve N-(dehidroasetik asit)-4-fenil-3-tiyosemikarbazit ile karışık ligandlı geçiş metal kompleksleri sentezlenmiş ve bazılarının biyolojik aktiviteleri incelenmiştir. 2-Aminobenzimidazol ve türevlerinden elde edilen proton transfer tuzu ve metal komplekslerinin de benzer biyolojik özellik gösterebileceği aşikardır.

Kaynakça

  • [1] Nowicka, A.; Nawrocka, W. P., (2013), Synthesis of selected drugs 2-amino-1H-benzimidazole derivatives. Wiadomosci Chemiczne, 67(7-8), 695-714.
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  • [4] Nowicka, A.; Nawrocka, W.P., (2013), Syntheses of selected new 2-amino-1H-benzimidazole derivatives and mechanism of their biological activity. Wiadomosci Chemiczne, 67(3-4), 203-225.
  • [5] Nawrocka, W.P.; Nowicka, A., (2013), Selected methods of the synthesis of 2-amino-1H-benzimidazole. Wiadomosci Chemiczne, 67(7-8), 715-732.
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  • [28] Mendiola, M.A.; Masaguer, J.R.; Molleda, C., (1992), Iron(II) chloride complexes with some 2-aminobenzimidazole ligands. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 22(7), 955-969.
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  • [33] Wang, X.G.; Li, J.; Ding, B.; Yang, E.C.; Zhao, X.J., (2008), A series of Cd(II) supramolecular architectures based on polycarboxylate and 2-aminobenzimidazole mixed-ligands. Journal of Molecular Structure, 876(1-3), 268-277.
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METAL COMPLEXES and BIOLOGICAL PROPERTIES of 2-AMINOBENZIMIDAZOLE

Yıl 2021, Sayı: 004, 19 - 28, 30.12.2021

Öz

There are studies in the literature that 2-aminobenzimidazole and its derivatives have antibacterial, anticancer, antiviral, anti-inflammatory, antiproliferative, antifungal, anthelmintic and antihistamine properties. 2-Aminobenzimidazole and its derivatives are bonded to metal ions with one and two teeth due to three nitrogen atoms in their structure. Simple metal complexes of 2-aminobenzimidazole and its derivatives were synthesized. In addition, mixed ligand metal complexes of between 2-aminobenzimidazole and other ligands {trimesic acid, terephthalic acid, isophthalic acid, glutaric acid, 2,6-pyridinedicarboxylic acid, 4-hydroxy-2,6-pyridinedicarboxylic acid, crotonic acid, oxalic acid,pyrazine-2-carboxylic acid, p-cymene, saccharin, dicyanamide, N-salicylidene-2-hydroxyaniline, acetoacetanilide, o-acetoacetoluidide, o-acetoacetanisidide, dehydroacetic acid, N-(dehydroacetic acid)-4-methyl-3-thiosemicarbazide, 4,4'-bipyridine, bis-(salicylaldehyde)phenylenimine, N- (dehydroacetic acid)-thiosemicarbazide, 4,5-dimethyl-N,N-bis(pyridine-2-yl-methylene)benzene-1,2- diimine, N-(dehydroacetic acid)-4-phenylsemicarbazide and N-(dehydroacetic acid)-4-phenyl-3- thiosemicarbazide} were synthesized and the biological activities of some of them were investigated. It is obvious that proton transfer salt and metal complexes obtained from 2-aminobenzimidazole and its derivatives can also exhibit similar biological properties.

Kaynakça

  • [1] Nowicka, A.; Nawrocka, W. P., (2013), Synthesis of selected drugs 2-amino-1H-benzimidazole derivatives. Wiadomosci Chemiczne, 67(7-8), 695-714.
  • [2] Nawrocka, W.P.; Nowicka, A.; Liszkiewicz, H., (2012), Biological activity of 2-amino-1H-benzimidazole derivatives. Part I. Wiadomosci Chemiczne, 66(9-10), 818-838.
  • [3] Nawrocka, W.P.; Nowicka, A.; Liszkiewicz, H.,, (2012), Biological activity of 2-amino-1H-benzimidazole derivatives. Part II. Wiadomosci Chemiczne, 66(9-10), 839-865.
  • [4] Nowicka, A.; Nawrocka, W.P., (2013), Syntheses of selected new 2-amino-1H-benzimidazole derivatives and mechanism of their biological activity. Wiadomosci Chemiczne, 67(3-4), 203-225.
  • [5] Nawrocka, W.P.; Nowicka, A., (2013), Selected methods of the synthesis of 2-amino-1H-benzimidazole. Wiadomosci Chemiczne, 67(7-8), 715-732.
  • [6] Nawrocka, W., (1996), Syntheses and pharmacological properties of new 2-aminobenzimidazole derivatives. Bollettino Chimico Farmaceutico, 135(1), 18-23.
  • [7] Rastogi, R.; Sharma, S., (1983), 2-Aminobenzimidazoles in Organic Syntheses, Synthesis, 11, 861-882.
  • [8] Holmes, I.; Naylor, A.; Alber, D.; Powell, J.R.; Major, M.R.; Negoita-Giras, G.; Allen, D.R.; Guetzoyan, L.J.; King, N.P.; Chapman, N.A., Preparation of anti-bacterial compounds based on amino-gold phosphine complexes. World Intellectual Property Organization, WO2017093545 A1 2017-06-08.
  • [9] Podunavac-Kuzmanovic, S.O.; Cvetkovic, D.M.; Vojinovic, L.S., (2004), Synthesis, physico-chemical characterization and biological activity of 2-aminobenzimidazole complexes with different metal ions. Acta Periodica Technologica, 35, 239-246.
  • [10] Podunavac-Kuzmanovic, S.O.; Cvetkovic, D.M.; (2004), Antimicrobial activity of cobalt(II) complexes with 2-aminobenzimidazole derivatives. Cetkovic, Gordana S. Acta Periodica Technologica, 35, 231-237.
  • [11] Lopez-Sandoval, H.; Londono-Lemos, M.E.; Garza-Velasco, R.; Poblano-Melendez, I.; Granada-Macias, P.; Gracia-Mora, I.; Barba-Behrens, N., (2008), Synthesis, structure and biological activities of cobalt(II) and zinc(II) coordination compounds with 2- benzimidazole derivatives. Journal of Inorganic Biochemistry, 102(5-6), 1267-1276.
  • [12] Ramadan, Ramadan M.; Abu Al-Nasr, Ahmad K.; Ali, Omayma A.M., (2018), Synthesis, spectroscopic, DFT studies and biological activity of some ruthenium carbonyl derivatives of bis-(salicylaldehyde)phenylenediimine Schiff base ligand. Journal of Molecular Structure, 1161, 100-107.
  • [13] Malik, B.A.; Maurya, R.C.; Mir, J.M.; Shah, F.F., (2016), Cobalt(II) bactericidal and heat resistant complexes of ONS donor Schiff base ligands: synthesis and combined DFT-experimental characterization. International Journal of Current Research in Chemistry and Pharmaceutical Sciences, 3(4), 50-72.
  • [14] Devi, T. C.; Krishnan, R.; Kunju, A.S., (2005), Synthesis and characterization of 2-amino-5-benzoylbenzimidazole complexes of manganese(II) and cobalt(II). Asian Journal of Chemistry, 17(2), 668-672.
  • [15] Campbell, M.J.M.; Card, D.W.; Grzeskowiak, R.; Goldstein, M., (1972), Complexes of 2-aminobenzimidazole with cobalt(II) and nickel(II). Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry, (15), 1687-1691.
  • [16] Ihara, Y.; Tsuchiya, R., (1980), Thermal square planar-to-octahedral transformation of nickel(II) complexes containing 2- aminobenzimidazole in the solid phase. Bulletin of the Chemical Society of Japan, 53(6), 1614-1617.
  • [17] Shukla, S.N.; Gaur, P.; Kaur, H.; Prasad, M., (2007), Synthesis and spectroscopic studies of some halogen-dimethylsulphoxide/tetramethylenesulphoxide-ruthenium(II) and ruthenium(III) complexes with 2-aminobenzimidazole. Journal of Coordination Chemistry, 60(10), 1047-1055.
  • [18] Matyakubov, A.A.; Masharipov, S.; Yunusov, Yu. T.; Askarov, M.A., (1988), Stabilization of PVC by some salts of 2-aminobenzimidazole derivatives. Doklady Akademii Nauk UzSSR, (7), 40-43.
  • [19] Tamayo, P.; Mendiola, M.A.; Masaguer, J.R.; Molleda, C., (1989), Tin(IV), titanium(IV) and vanadium(IV) chloride complexes with 2-aminobenzimidazole and 2-(2'- aminophenyl)benzimidazole. Transition Metal Chemistry (Dordrecht, Netherlands), 14(4), 283-286.
  • [20] Ardizzoia, G.A.; Brenna, S.; Castelli, F.; Galli, S.; Masciocchi, N.; Maspero, A., (2008), Synthesis and characterization of 2-amino-1H-benzimidazole group 11 coordination polymers: a combined x-ray powder diffraction and 13CP/MAS NMR study. Inorganic Chemistry Communications, 11(5), 502-505.
  • [21] Campbell, M.J.M.; Grezeskowiak, R.; Juneja, S.G., (1974), Copper(II) complexes with 2-aminobenzimidazole and 2-(aminomethyl)benzimidazole. Journal of Inorganic and Nuclear Chemistry, 36(11), 2485-2488.
  • [22] Zhao, X.J.; Li, J.; Ding, B.; Wang, X.G.; Yang, E.C., (2007), The irreversible crystal transformation of a novel Cadmium(II) supramolecular complex containing planar tetrameric water cluster. Inorganic Chemistry Communications, 10(5), 605-609.
  • [23] Garnovskii, D.A.; Antsyshkina, A.S.; Sadimenko, A.P.; Porai-Koshits, M.A.; Osipov, O.A.; Garnovskii, A.D., (1987), Reasons for the decrease in primary amine-group stretching frequencies in the adducts of Lewis acid with 2-aminoheterocycles. Doklady Akademii Nauk SSSR, 296(5), 1119-1121.
  • [24] Esparza-Ruiz, A.; Pena-Hueso, A.; Mijangos, E.; Osorio-Monreal, G.; Noeth, H.; Flores-Parra, A.; Contreras, R.; Barba-Behrens, N., (2011), Cobalt(II), nickel(II) and zinc(II) coordination compounds derived from aromatic amines. Polyhedron, 30(12), 2090-2098.
  • [25] Kessentini, A.; Belhouchet, M.; Sunol, J.J.; Abid, Y.; Mhiri, T., (2013), Synthesis, crystal structure, vibrational spectra, optical properties and theoretical investigation of bis- (2-aminobenzimidazolium) tetraiodocadmate. Journal of Molecular Structure, 1039, 207-213.
  • [26] Zhao, H.K.; Wang, X.G.; Yang, E.C.; Zhao, X.J., (2008), Synthesis and Crystal Structure of a Mixed-Ligand Cobalt(II) Complex with 2-Aminobenzimidazole. Journal of Chemical Crystallography, 38(8), 625-629.
  • [27] Hosny, W.M.; Mohamed, G.G., (2001), Thermodynamic and multinuclear magnetic resonance study of dimethyltin(IV) complexes with some imidazoles in aqueous solutions. Annali di Chimica (Rome, Italy), 91(1-2), 81-92.
  • [28] Mendiola, M.A.; Masaguer, J.R.; Molleda, C., (1992), Iron(II) chloride complexes with some 2-aminobenzimidazole ligands. Synthesis and Reactivity in Inorganic and Metal-Organic Chemistry, 22(7), 955-969.
  • [29] Marcos, M.L.; Garcia-Vazquez, J.A.; Masaguer, J.R.; Molleda, C., (1987), Cobalt(II) and iron(III) complexes with 2-substituted benzimidazole derivatives.Transition Metal Chemistry (Dordrecht, Netherlands), 12(4), 352-355.
  • [30] Ramadan, R.M.; El-Medani, S.M.; Ali, O.A.M.; Mohamed, H.A., (2004), Spectroscopic and thermal studies of some Palladium complexes with certain Heterocyclic Nitrogen ligands. Journal of Coordination Chemistry, 57(5), 373-379.
  • [31] Maurya, R.C.; Mishra, D.D.; Awasthi, S.; Mukherjee, S., (1991), Synthesis, magnetic, and spectral studies of some novel cyanonitrosyl {CrNO5} complexes of chromium(I) involving benzimidazole derivatives. National Academy Science Letters (India), 14(1), 21-23.
  • [32] Devi, T.C.; Krishnan, R.; Kunju, A.S., (2004), Synthesis and characterization of nickel(II), zinc(II) and cadmium(II) complexes of 2-amino-5-benzoylbenzimidazole and nickel(II) complexes of 2-(2'-hydroxynaphthylazo)-5-benzoylbenzimidazole. Oriental Journal of Chemistry, 20(3), 561-566.
  • [33] Wang, X.G.; Li, J.; Ding, B.; Yang, E.C.; Zhao, X.J., (2008), A series of Cd(II) supramolecular architectures based on polycarboxylate and 2-aminobenzimidazole mixed-ligands. Journal of Molecular Structure, 876(1-3), 268-277.
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  • [35] Al-Jibori, S.A.; Habeeb, A.T.; Al-Jibori, G.H.H.; Dayaaf, N.A.; Merzweiler, K.; Wagner, C.; Schmidt, H.; Hogarth, G., (2014), Palladium(II) saccharinate (sac) and thiosaccharinate (tsac) complexes with supporting amino- and acetylamino-thiazole ligands: Crystal structures of trans-[PdCl2(abzt)2]·dmf (abzt = 2-aminobenzothiazole), trans-[PdCl2(bzta)2].dmf (bzta = 2-acetylaminobenzothiazole) and trans-[Pd(sac)2(abzt)2]·2dmf. Polyhedron, 67, 338-343.
  • [36] Das, A.; Bhattacharya, B.; Maity, D.K.; Halder, A.; Ghoshal, D., (2016), Construction of five dicyanamide based coordination polymers with diverse dimensionality: Synthesis, characterization and photoluminescence study. Polyhedron, 117, 585-591.
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  • [50] Turhan, İ. Bazı benzimidazol türevlerinin proton transfer tuzları ve onların metal komplekslerinin sentezi ve kullanım alanlarının araştırılması. Kütahya Dumlupınar Üniversitesi Fen Bilimleri Enstitüsü, Doktora Tezi, 2018.
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Toplam 51 adet kaynakça vardır.

Ayrıntılar

Birincil Dil Türkçe
Bölüm Derlemeler
Yazarlar

Halil İlkimen Bu kişi benim 0000-0003-1747-159X

Sabiha Gözde Salün Bu kişi benim 0000-0001-7114-0711

Birsel İlkimen Bu kişi benim 0000-0002-6022-9187

Yayımlanma Tarihi 30 Aralık 2021
Gönderilme Tarihi 29 Nisan 2022
Yayımlandığı Sayı Yıl 2021 Sayı: 004

Kaynak Göster

APA İlkimen, H., Salün, S. G., & İlkimen, B. (2021). 2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ ve BİYOLOJİK ÖZELLİKLERİ. Journal of Scientific Reports-B(004), 19-28.
AMA İlkimen H, Salün SG, İlkimen B. 2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ ve BİYOLOJİK ÖZELLİKLERİ. JSR-B. Aralık 2021;(004):19-28.
Chicago İlkimen, Halil, Sabiha Gözde Salün, ve Birsel İlkimen. “2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ Ve BİYOLOJİK ÖZELLİKLERİ”. Journal of Scientific Reports-B, sy. 004 (Aralık 2021): 19-28.
EndNote İlkimen H, Salün SG, İlkimen B (01 Aralık 2021) 2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ ve BİYOLOJİK ÖZELLİKLERİ. Journal of Scientific Reports-B 004 19–28.
IEEE H. İlkimen, S. G. Salün, ve B. İlkimen, “2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ ve BİYOLOJİK ÖZELLİKLERİ”, JSR-B, sy. 004, ss. 19–28, Aralık 2021.
ISNAD İlkimen, Halil vd. “2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ Ve BİYOLOJİK ÖZELLİKLERİ”. Journal of Scientific Reports-B 004 (Aralık 2021), 19-28.
JAMA İlkimen H, Salün SG, İlkimen B. 2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ ve BİYOLOJİK ÖZELLİKLERİ. JSR-B. 2021;:19–28.
MLA İlkimen, Halil vd. “2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ Ve BİYOLOJİK ÖZELLİKLERİ”. Journal of Scientific Reports-B, sy. 004, 2021, ss. 19-28.
Vancouver İlkimen H, Salün SG, İlkimen B. 2-AMİNOBENZİMİDAZOLÜN METAL KOMPLEKSLERİ ve BİYOLOJİK ÖZELLİKLERİ. JSR-B. 2021(004):19-28.