The Importance of 2-AminoThiazole Schiff Bases as Antimicrobial and Anticancer Agents
DOI:
https://doi.org/10.23851/mjs.v31i3.865Keywords:
Pharmacophore 2-aminothiazole, Schiff bases, Metal complexesAbstract
The pharmacophore 2-aminothiazole has an interesting role in pharmaceutical chemistry as this led to the synthesis of many types of compounds with diverse biological activity. Schiff base derivatives at the same time contribute to drug evolution importantly. In this review, the Schiff base derivatives of 2-aminothiazole formed and some of their metal complexes are being focused on, and the antimicrobial and anticancer activity of them is being illustrated.
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Narendra S., Uma S. Sharma, Niranjan S., Sushil K. and Umesh K. Sharma, Synthesis and antimicrobial activity of some novel 2-amino thiazole derivatives, J. Chem. Pharm. Res.; 2010, 2(3):691-698.
Entesar O. Al-Tamimi and Hussein F. Abdul Mahdi, Synthesis and Characterization of New Compounds containing 2-amino Thiazole Ring from Amino Benzoic Acid, Int. J. Curr. Microbiol. App. Sci; 2016, 5(8): 1-13.
Ankit Kr. Jain, Rajeev k Singla, Birendra Shrivastava, Thiazole: A Remarkable Antimicrobial And Antioxidant Agents, Newsletter; 2011, 2:1072-1084.
Tsuji, K.; Ishikawa, H., Synthesis and anti-pseudomonal activity of new 2-isocephems with a dihydroxypyridone moiety at C-7, Bioorg. Med. Chem. Lett.; 1994, 4: 1601-06.
Nedaa A. A. Rahim and Ammar A Mahmood Kubba, Synthesis, Characterization and Antimicrobial Evaluation with DFT Study of New Two-Amino-4-(4-Chlorophenyl) Thiazole Derivatives, Iraqi J Pharm Sci; 2018, 27(1): 79-88.
Karabasanagouda T., Adhikari A V., Dhanwad R., and Parameshwarappa G., Synthesis of Some New 2-(4Alkylthiophenoxy)-4-Substituted-1, 3Thiazoles As Possible AntiInflammatory And Antimicrobial Agents, Indian J. Chem.; 2008, 47b: 144-152.
Khan KM., Ambreen N., Karim A., Saied S., Amyn A., Ahmed A., and Perveen S., Schiff Bases Of Thiazole As Antibacterial And Antifungal Agents, J. Pharmacy Res.; 2012, 5: 651-656.
Frank, W. B., Amanda, S. C., Marita, H.S., Richard, J., Nils, G.J., Et.Al, Phenethylthiazolethiourea (Pett) Compounds, A New Class Of Hiv-1 Reverse Transcriptase Inhibitors. 1. Synthesis and Basic Structure-Activity Relationship Studies Of Pett Analogs, J. Med. Chem.; 1995, 38: 4929-36.
P. Bhattacharya, j. T. leonard, K. Roy, Bioorg., Exploring QSAR of thiazole and thiadiazole derivatives as potent and selective human adenosine A3 receptor antagonists using FA and GFA techniques, Med. Chem.; 2005,13(4): 1159-1165.
Kumar Y., Green R., Wise DS. , Wotring LL., and Townsend LB., Synthesis Of 2,4-Disubstituted Thiazoles And Selenazoles As Potential Antifilarial And Antitumor Agents. 2. 2-Arylamido And 2-Alkylamido Derivatives Of 2-Amino4-(Isothiocyanatomethyl)Thiazole And 2-Amino-4-(Isothiocyanatomethyl) Selenazole, J. Med. Chem.; 1993, 36: 3849-3852.
Zhi-Hua Zhang, Hong-Mei Wu, Sai-Nan Deng, Xiao-Yu Cai, Yu Yao, Muriira Cyrus Mwenda, et.al., Design, Synthesis, and Anticancer Activities of Novel 2-Amino-4-phenylthiazole Scaffold Containing Amide Moieties, Hindawi Journal of Chemistry; 2018:1-8.
Fortuna, H.; James, D.R.; Robert, W.D.; Francis, A.K.; Roland, L.W; Steven P.S.; James, H.H.; Patrick, R.Y.; George W.C. 3-[1-(2-Benzoxazolyl) hydrazino] propanenitrile derivatives: inhibitors of immune complex induced inflammation, J. Med. Chem.; 1988, 31: 1719-28.
Gindher, T.; Reddy, R. B.; Prasanna, B.; Chandra Mouli, G. V. P.; Synthesis and pharmacological evaluation of thiazoles, Ind. J. Chem.; 2001, 40B: 1279.
Chandra B. Mishra, Shikha Kumari, Manisha Tiwari, Thiazole: A promising heterocycle for the development of potent CNS active agents, European Journal of Medicinal Chemistry; 2015, 92: 1-34.
K. D. Hargrave, F. K. Hess, J. T. Oliver, N-(4-Substituted-Thiazolyl) Oxamic Acid Derivatives, A New Series of Potent, Orally Active Antiallergy Agents, J. Med. Chem.; 1983, 26 (8): 1158-63.
W. C. Patt, H. W. Hamilton, M. D. Taylor, et al., Structure-activity relationships of a series of 2-amino-4-thiazole-containing renin inhibitors, J. Med. Chem.; 1992, 35(14): 2562-72.
N. G. ergenc, N. S. capan, S. Gunay, m. Ozkirimli Gungor, S. Ozbey, e. Kendi, Synthesis and hypnotic activity of new 4-thiazolidinone and 2-thioxo-4,5-imidazolidinedione derivatives, Arch. Pharm. Pharm. Med. Chem.; 1999, 332: 343-347.
Cartner J.S., Kramer S., Talley J.J., Penning T and Collins P., Synthesis and activity of sulfonamide-substituted 4, 5-diaryl thiazoles as selective cyclo oxygenase-2 inhibitors, Bioorg. Med.Chem. Lett.; 1999: 1171-1174
Badore A., Bordes M.F., de Cointet P., Savi P. and Bernat A. et. al., New orally active non-peptide fibrinogen receptor (GpIIb-IIIa) antagonists: Idenfictionofethy l3-(N-(4-(-Amino (ethoxycarbonyl)imino)methyl)phenyl)-1,3 thiazole-2-yl)-N-(1-ethoxycarbonyl) methyl)piperid-4-yl amino) propionate (SR121787) as potent and long acting antithrombotic agent, Journal of Med. Chemistry; 1997, 40: 3393-3401.
Laine, L.; Kivitz, A.J.; Bello, A.E.; Grahn, A.Y.; Schiff, M.H.; Taha, A.S. Double-blind randomized trials of single-tablet ibuprofen/high-dose famotidine vs. ibuprofen alone for reduction of gastric and duodenal ulcers, Am. J. Gastroenterol; 2012, 107: 379-386.
Das D, Sikdar P, Bairagi M. Recent developments of 2-aminothiazoles in medicinal chemistry, European Journal of Medicinal Chemistry; 2016, 109:89-98.
Borelli, C.; Schaller, M.; Niewerth, M.; Nocker, K.; Baasner, B.; Berg, D.; Tiemann, R.; Tietjen, K.; Fugmann, B.; Lang-Fugmann, S.; et al. Modes of action of the new arylguanidine abafungin beyond interference with ergosterol biosynthesis and in vitro activity against medically important fungi, Chemotherapy; 2008, 54: 245-259.
Guay, D.R.P. Cefdinir: An advanced-generation, broad-spectrum oral cephalosporin, Clin. Ther; 2002, 24: 473-489.
Luger P, Daneck K, Engel W, Trummlitz G, Wagner K. Structure and physicochemical properties of meloxicam, a new NSAID, EurJPharmSci.; 1996, 4(3):175-87.
Adileh Ayati, Saeed Emami, Setareh Moghimi, Alireza Foroumadi, Thiazole in the targeted anticancer drug discovery, FutureMed.Chem. 2019, 11(15): 1929-1952.
Bang-Chi C., Rulin Z., Bei Wang, Roberto D., Jean L., Pierre S., Masaki E., Balu B., and Joel C. Barrisha , A new and efficient preparation of 2-aminothiazole-5-carbamides: applications to the synthesis of the anti-cancer drug dasatinib , ARKIVOC; 2010, 6: 32-38.
Katarzyna B., El?bieta L.Chruscinska, Schiff bases -interesting range of applications in various fields of science, CHEMIK; 2014, 68, (2): 129-134.
Anant P., Devjani A., Application of Schiff bases and their metal complexes-A Review, IJCRGG; 2011, 3, (4): 1891-1896.
Wenling Q., Sha L., Mauro P. and Stefano B., Schiff Bases: A Short Survey on an Evergreen Chemistry Tool, Molecules; 2013, 18(10): 12264-12289.
Mithun R. and Biplab D., Chemistry & Biological importance of Heterocyclic Schiff Bases, International Research Journal of Pure & Applied Chemistry; 2013, 3(3): 232-249.
Anita Rani, Manoj Kumar, Rajshree Khare and Hardeep Singh Tuli, Schiff bases as an antimicrobial agent: A review, Journal of Biological and Chemical Sciences; 2015, 2(1): 62-91.
Anand P, Patil VM, Sharma VK, Khosa RL, Masand N. Schiff bases: A Review on Biological Insights, Int J Drug Design Dis; 2012, 3: 851.
Muthal B.N., Raut B.N., Tekale A.S., Synthesis, characterization, stability constant and microbial activity of schiff bases and their CoII, NiII, CuII & ZnII Metal Chelates, International Journal of Chemical Studies; 2015, 3(2): 12-16.
Kashyap SJ, Garg VK, Sharma PK, Kumar N, Dudhe R, Gupta JK. Thiazoles: having diverse biological activities, Med Chem Res; 2012, 21: 2132.
More PG, Karale NN, Lawanda AS, Rajmane SV, Pawar SV, Patil RH. A 4-(o-methoxyphenyl)-2-aminothiazole: an anti-quorum sensing compound, Med Chem Res; 2013, 22: 4183.
More PG, Karale NN, Lawanda AS, Narang N, Patil RH. Synthesis and anti-biofilm activity of thiazole Schiff bases, Med Chem Res; 2014, 23: 790.
Patel RN. Structural, magnetic and spectroscopic characterization of two unusual end-on bis(?-acetato/?-nitrato) bridged copper(II) complexes with N?-[phenyl(pyridin-2-yl)methylidene]furan-2carbohydrazide and (2E,4Z)-N,2-dimethylhepta-2,4,6-trienamide-1-phenyl -1-pyridin-2-ylmethanimine (1:1) as capping ligands. Inorg Chim Acta; 2010, 363: 3838.
Wu H, Kou F, Jia F, Liu B, Yuan J, Bai YJ. Synthesis, Crystal Structure, and Spectra Properties of the Cadmium (II) Complex with Bis (N-allylbenzimidazol-2-ylmethyl) benzylamine, Photochem Photobiol B: Biolog; 2011, 105: 190.
Gulrez N., Riyaz S., Antimicrobial, electrochemical and thermodynamic studies of Schiff base complexes and their potential as anticarcinogenic and antitumor agents: A review, IOSR Journal of Applied Chemistry; 2017, 10, (10): 40-51.
Buchheidt D, Skladny H, Baust C, Hehlmann R. Systemic infections with Candida sp. and Aspergillus sp. in immunocompromised patients with hematological malignancies: current serological and molecular diagnostic methods, Chemotherapy; 2000, 46: 219.
Li Y, Zheng YY, Ming FW. Synthesis, characterization, DNA binding properties and antioxidant activity of Ln (III) complexes with hesperetin-4-one-(benzoyl) hydrazine, Eur J Med Chem; 2009, 44(11):4585-95.
Nicola M, Cristin M, Valentina G, Domenico O, Mauro R, Elisabetta G, et al. Revisiting [Pt Cl2(cis-1,4-DACH)]: An Underestimated Antitumor Drug with Potential Application to the Treatment of Oxaliplatin-Refractory Colorectal Cancer, J Med Chem ; 2012, 55(16):7182-92.
Olga N, Jana K, Vendula B, Ctirad H, Marie V, Haimei C, et al. Conformation of DNA modified by monofunctional Ru (II) arene complexes: Recognition by DNA binding proteins and repair. Relationship to cytotoxicity, Chem Biol; 2005, 12(1):121-9.
Shambuling K., Parvati A., Irfan N. Shaikh, Basavaraj M. Kalshetty, Synthesis, Characterization and Antimicrobial Activity of some Metal Complexes Derived from Thiazole Schiff Bases with In-vitro Cytotoxicity and DNA Cleavage Studies, Indian Journal of Pharmaceutical Education and Research; 2017, 51 (3): 490-501.
Amith KS, Sulekh C. Complexation of Nitrogen and Sulphur donor Schiff's Base Ligand to Cr (III) and Ni (II) metal ions: Synthesis, Spectroscopic and Antipathogenic Studies, Spectrochimica Acta A; 2011, 78(1):337-42.
Zahid. HC, Arif M, Muhammad AA, Claudiu TS. Metal Based antibacterial and antifungal agents: Synthesis, Characterization, and In vitro Biological evaluation of Co(II), Cu (II), Ni (II), and Zn (II) complexes with Amino acidderived Compounds, Bioinorganic Chemistry and Applications; 2006: 1- 13.
Abd El-Wahab ZH, Mahmoud MM, Salman AA, El-Shetary BA, Faheim AA. Co (II), Ce (III) and UO2 (VI) Bis-Salicylatothiosemicarbazide Complexes: Binary and Ternary complexes, thermal studies and antimicrobial activity, Spectrochimica Acta A; 2004, 60(12):2861-73.
J Senthil Kumaran, S Priya, J Gowsika, N Jayachandramani S and Mahalakshmi, Synthesis, Spectroscopic Characterization, In Silico DNA Studies and Antibacterial Activites of Copper(Ii) and Zinc(Ii) Complexes derived from Thiazole based Pyrazolone Derivatives, Research Journal of Pharmaceutical, Biological and Chemical Sciences; 2013, 4 (2): 279.
Belaid S, Landreau A, Djebbar S, Benali-Baitich O, Bouet G, Bouchara J P,Synthesis, characterization and antifungal activity of a series of manganese(II) and copper(II) complexes with ligands derived from reduced N,N'-O-phenylenebis(salicylideneimine), J Inorg Biochem ; 2008, 102 (1):63-69.
Dharamaraj N, Viswanathamurthi P, Natarajan K, Ruthenium(Ii) Complexes Containing Bidentate Schiff Bases and Their Antifungal Activity, Trans Met Chem; 2001, 26 (1-2): 105-109.
Azam F., Singh S., Khokhra S. Lal, Prakash O., Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2'-hydroxy) benzylideneaminonaphthothiazole as potential antimicrobial agents, J Zhejiang Univ Sci B; 2007 8(6):446-452.
S. K. Sengupta, O. P. Pandey, B. K. Srivastava, V. K. Sharma, Synthesis, structural and biochemical aspects of titanocene and zirconocene chelates of acetylferrocenyl thiosemicarbazones; Transition Met. Chem; 1998, 23(4): 349-353.
J. Parekh, P. Inamdhar, R. Nair, S. Baluja, S. Chandra, Synthesis and antibacterial activity of some Schiff bases derived from 4-aminobenzoic acid; J. Serb. Chem. Soc; 2005, 70(10):1155-116.
Y. Vaghasia, R. Nair, M. Soni, S. Baluja, S. Chandra, Synthesis, structural determination and antibacterial activity of compounds derived from vanillin and 4-aminoantipyrine; J. Serb. Chem. Soc.; 2004, 69 (12): 991-998.
B.C.J. Bayer; An introduction to ligand field. McGraw Hill, New York, 1962.
A.B.P. Lever; Inorganic electronic spectroscopy Elsevier, Amsterdam, 1984.
Hassan UM, Chohan ZH, Supuran CT, Antibacterial Zn(II) compounds of Schiff base derived from some benzothiazoles; Main Group Met Chem; 2002, 25(5): 291-296.
Shrivastava G, Shrivastava M, Shrivastava G; Antimicrobial activity of Schiff Base of 2-Amino 5Nitrothiazole and its Copper complex; PharmaTutor; 2018, 6(9): 1-5.
A. S. Thakar, K. S. Pandya, K. T. Joshi, A. M. Pancholi, Synthesis, Characterization and Antibacterial Activity of Novel Schiff Bases Derived from 4-Phenyl-2-aminothiazole and their Mn(II), Fe(II), Co(II), Ni(II) and Cu(II) Metal complexes, E-Journal of Chemistry; 2011, 8(4): 1556-1565.
Ambit T., Krishenakant J., Kishor P. and ARVIND P., Coordination Modes of a Schiff Base Derived from Substituted 2-Aminothiazole with Chromium(III), Manganese(II), Iron(II), Cobalt(II), Nickel(II) and Copper(II) Metal Ions: Synthesis, Spectroscopic and Antimicrobial Studies, E-Journal of Chemistry; 2011, 8(4): 1750-1764.
Nikhil D. Amnerkar, Bhoomendra A. Bhongade, Kishore P. Bhusari, Synthesis and biological evaluation of some 4-(6-substituted-1,3-benzothiazol-2-yl) amino-1,3-thiazole-2-amines and their Schiff bases, Arabian Journal of Chemistry; 2015, 8: 545-552.
Pushkal S., Ritu S., Santosh K. Srivastava and Savitri D. Srivastava, Synthesis of 2-oxoazetidine derivatives of 2-aminothiazole and their biological activity, J. Serb. Chem. Soc.; 2012, 77 (5): 599-605.
Rajul G., Neeraj K. Fuloria, Shivkanya F., Synthesis and Antimicrobial Profile of Some Newer 2-Aminothiazole Derivatives, Turk J Pharm Sci; 2013, 10 (3): 425-434.
Rajul G., Neeraj K. Fuloria, Shivkanya F., Synthesis and Antimicrobial Activity Evaluation of some Schiff Bases Derived From 2-Aminothiazole Derivatives, Indonesian J. Pharm.; 2013, 24 (1): 35 - 39.
R. Karki, G.K. Rao, A. Gupta, G. Mariappan, S.Adhikari, Synthesis, Characterization and Antimicrobial Activities of Schiff bases of 2-amino-4-(O-chloroanilino)-1, 3-thiazole, Journal of Applied Pharmaceutical Science; 2013, 3 (07): 093-096.
Vinusha HM, Shiva Prasad K, Chandan S and Muneera Begum, Imino-4-Methoxyphenol Thiazole Derived Schiff Base Ligands: Synthesis, Spectral Characterization and Antimicrobial Activity, Chem Sci J; 2015, 6(3):1-4.
Xin Z., Ling S., Zhong J., Jian-Bing L., Hong D., and Jian-Xin F., Synthesis and Antitumor Activity Evaluation of Some Schiff Bases Derived from 2-Aminothiazole Derivatives, Heteroatom Chemistry; 2007, 18 (1): 55-59.
A. Palanimurugan, A. Kulandaisamy, DNA, in vitro antimicrobial/anticancer activities and biocidal based statistical analysis of Schiff base metal complexes derived from salicylalidene-4-4imino-2,3-dimethyl-1-phenyl-3-pyrazolin-5-one and 2-aminothiazole, Journal of organometallic chemistry; 2018, 861: 263-274.
Minghua L, Seung WK, Yoojin S. Discovery of 2-aminothiazole derivatives as anticancer agents. Bulletin of Korean society; 2010, 31(6):1463-1464.
Jeong TC, Koh WS, Kwon BM, Yoon SY. Cinnamaldehyde inhibits lymphocyte proliferation and modulates T-cell differentiation. International Journal of Immunopharmacology; 1998, 20 (11):643-660.
Shruthy V. S, ShaKkkeela Y., In Silico Design, Doking, Synthesis And Evaluation Of Thiazole Schiff Bases, International Journal of Pharmacy and Pharmaceutical Sciences; 2014, 6 (3): 271-275.
Nikhil M. Parekh, Bhupendra M. Mistry, Muthuraman P., Surendra K. Shinde, Rahul V Patel, Investigation of Anticancer Potencies of Newly Generated Schiff Base Imidazolylphenylheterocyclic-2-Ylmethylenethiazole-2-Amines, Chinese Chemical Letters; 2017, 28:602-606.
Saima Ejaz1, Humaira Nadeem, Rehan Zafar Paracha, Sadia Sarwar and Sadaf Ejaz, Designing, Synthesis and Characterization of 2-Aminothiazole-4-Carboxylate Schiff Bases; Antimicrobial Evaluation Against Multidrug Resistant Strains and Molecular Docking, Bmc Chemistry; 2019, 115: 1-13.
Zahra Aldelfy, Zeki Al-Shamkani, Mohammed Al-Assadi, 2-Hydroxybenzylidene-4-(4-Substitutedphenyl)-2-Amino Thiazole and Their Pt (Ii) Complexes: Synthesis, Characterization and Biological Study, Egypt.J.Chem. 2019, 62(10): 1851 - 1867.
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