Generic placeholder image

Mini-Reviews in Medicinal Chemistry

Editor-in-Chief

ISSN (Print): 1389-5575
ISSN (Online): 1875-5607

Review Article

A Review on Recent Synthetic Strategies and Pharmacological Importance of 1,3-Thiazole Derivatives

Author(s): Swarnagowri Nayak and Santhosh L. Gaonkar*

Volume 19, Issue 3, 2019

Page: [215 - 238] Pages: 24

DOI: 10.2174/1389557518666180816112151

Price: $65

Abstract

Thiazole is the most common heterocyclic compound in heterocyclic chemistry and in drug design. Presence of several reaction sites in the thiazole moiety extends their range of applications and leads to new solutions for challenges in synthetic and medicinal chemistry. Thiazole derivatives are widely used as bioactive agents, liquid crystals, sensors, catalysts, etc. The motivating molecular architecture of 1,3-thiazoles makes them suitable moieties for drug development. In this review, our aim is to corroborate the recent data available on various synthetic strategies and biological properties of 1,3- thiazole derivatives.

Keywords: 2-substituted thiazole, 2, 4-substituted thiazole, 2, 5-substituted thiazole, 2, 4, 5-substituted thiazole, fused thiazole, anti-microbial activity, anti-cancer activity, antioxidant activity.

Graphical Abstract

[1]
Rashad, A.E.; Mahmoud, A.E.; Ali, M.M. Synthesis and anticancer effects of some novel pyrazolo [3,4-d]pyrimidine derivatives by generating reactive oxygen species in human breast adenocarcinoma cells. Eur. J. Med. Chem., 2011, 46, 1019-1026.
[2]
Xinjiang, W.; Fekadu, K.; Volker, M-S. Induction of apoptosis in tumour cells by naturally occurring sulfer-containing compounds. Mutat. Res., 2005, 589, 81-102.
[3]
Karegoudar, P.; Karthikeyan, M.S.; Prasad, D.J.; Mahalinga, M.; Holla, B.S.; Kumari, N.S. Synthesis of some novel 2,4-disubstituted thiazoles as possible antimicrobial agents. Eur. J. Med. Chem., 2008, 43, 261-267.
[4]
Cukurovali, A.; Yilmaz, I.; Gur, S.; Kazaz, C. Synthesis, the antibacterial and antifungal activity of some new thiazolylhydrazone derivatives containing 3-substituted cyclobutane ring. Eur. J. Med. Chem., 2006, 41, 201-207.
[5]
Snyder, N.L.; Boisvert, C.J. Hantzsch synthesis. Name reactions in heterocyclic chemistry II. Jie-Jack Li editor, J. Wiley & Sons, Inc., Hoboken, New Jersey; 2011, 591-644.
[6]
Kemson, J. Hantzsch thiazole synthesis. Name reactions in heterocyclic chemistry II. Jie-Jack Li editor, J. Wiley & Sons, Inc., Hoboken, New Jersey; 2011, 299-308.
[7]
Abele, E.; Abele, R.; Lukevics, E. Oximes of five-membered heterocyclic compounds with two heteroatoms 2. Reactions and biological activity (Review). Chem. Heterocycl. Compd., 2007, 43, 945-977.
[8]
Guray, T.; Ackkalp, E.; C, Ogretir. Yarlıgan, S. Quantum chemical studies on protonation of some substituted thiazole derivatives. J. Mol. Graph. Model., 2007, 26, 154-165.
[9]
Sukanta, K.; Kimberly, M.; Edward, R.B. Microwave-assisted Hantzsch thiazole synthesis of N-phenyl-4-(6-phenylimidazo [2,1-b]thiazol-5-yl)thiazol-2-amines from the reaction of 2-chloro-1-(6-phenylimidazo [2,1-b]thiazol-5-yl)ethanones and thioureas. Tetrahedron Lett., 2012, 53, 4921-4924.
[10]
Banothu, J.; Vaarla, K.; Bavantula, R.; Chin, P.A. Sodium fluoride as an efficient catalyst for the synthesis of 2,4-disubstituted-1,3-thiazoles and selenazoles at ambient temperature. Chem. Lett., 2014, 25, 172-175.
[11]
Kiryanov, A.A.; Sampson, P.; Seed, A.J. Synthesis of 2-alkoxy-substituted thiophenes, 1,3-thiazoles, and related S-heterocycles via Lawesson’s reagent-mediated cyclization under microwave irradiation: applications for liquid crystal synthesis. J. Org. Chem., 2001, 66, 7925.
[12]
Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. Facile Synthesis of 2,5-Diarylthiazoles via Palladium-Catalyzed Tandem C−H Substitutions. Design of Tunable Light Emission and Liquid Crystalline Characteristics. J. Am. Chem. Soc., 2003, 125, 1700.
[13]
Kim, B-Y.; Kim, H-S.; Helal, A. A fluorescent chemosensor for sequential recognition of gallium and hydrogen sulfate ions based on a new phenylthiazole derivative. Sens. Actuators B Chem., 2015, 206, 430.
[14]
Bach, T.; Heuser, S. Synthesis of 2-(o-hydroxyaryl)-4-arylthiazoles by regioselective Pd(0)-catalyzed cross-coupling. Tetrahedron Lett., 2000, 41, 1707.
[15]
White, M.J.; Leeper, F.J. Kinetics of the thiazolium ion-catalyzed benzoin condensation. J. Org. Chem., 2001, 66, 5124-5131.
[16]
Huo, J.; Zeng, H. A novel triphenylamine functionalized bithiazole–metal complex with C60 for photocatalytic hydrogen production under visible light irradiation. J. Mater. Chem., 2015, 3, 6258.
[17]
Guo, X.G.; Quinn, J.; Chen, Z.H.; Usta, H.; Zheng, Y.; Xia, Y.; Hennek, J.W.; Ortiz, R.P.; Marks, T.J.; Facchetti, A. Dialkoxybithiazole: A new building block for head-to-head polymer semiconductors. J. Am. Chem. Soc., 2013, 135, 1986-1996.
[18]
Pammer, F.; Jäger, J.; Rudolf, B.; Sun, Y. Soluble Head-to-Tail Regioregular Polythiazoles: Preparation, properties, and evidence for chain-growth behavior in the synthesis via kumada-coupling polycondensation. Macromolecules, 2014, 47, 5904.
[19]
Chhabria, M.T.; Patel, S.; Modi, P.; Brahmkshatriya, P.S. Thiazole: A review on chemistry, synthesis and therapeutic importance of its derivatives. Curr. Top. Med. Chem., 2016, 16, 2841-2864.
[20]
Varghese, N.; Jacob, J.; Mythri, M.; Nija, B.; Sheeba, J.T.S. Synthesis of thiazole derivatives—A Review. World J. Pharm. Pharm. Sci., 2016, 5, 624-636.
[21]
Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M. Novel thiazole derivatives: A patent review (2008 -- 2012; Part 1). Expert Opin. Ther. Pat., 2014, 24, 201-216.
[22]
Bouherrou, H.; Saidoun, A.; Abderrahmani, A.; Abdellaziz, L.; Rachedi, Y.; Dumas, F.; Demenceau, A. Synthesis and biological evaluation of new substituted hantzsch thiazole derivatives from environmentally benign one-pot synthesis using silica supported tungstosilisic acid as reusable catalyst. Molecules, 2017, 22(5), 757.
[23]
Qiao, Q.; So, S.S.; Goodnow, Jr, R.A. Stereochemical control factors in the hantzsch thiazole synthesis: A hammett substitution correlation analysis. Org. Lett., 2001, 3, 3655.
[24]
Guernon, J.M.; Yong-Jin, W. 3-Bromocyclohexane-1,2-dione as a useful reagent for Hantzsch synthesis of thiazoles and the synthesis of related heterocycles. Tetrahedron Lett., 2011, 52, 3633-3635.
[25]
Gabriel, S. Synthese von Oxazolen und thiazolen II. Eur. J. Inorg. Chem., 1910, 43, 1283-1287.
[26]
Wildeman, J.; Van Leusen, A.M. Chemistry of sulfonylmethyl isocyanides. 14. Synthesis of 1,3-Thiazoles from carbon-disulfide and tosylmethyl isocyanide under phase-transfer conditions; Synthesis-Stuttgart, 1977, pp. 501-502.
[27]
Rajappa, S.; Nair, M.D.; Advani, B.G.; Sreenivasan, R.; Desai, J.A. A General Synthesis of Thiazoles. Part 3. Comparative evaluation of different functionalised thioureas as precursors. Chem. Soc. Perkin Trans., 1979, I, 1762-1764.
[28]
Babar, A.; Khalid, H.; Ayub, K.; Saleem, S.; Waseem, A.; Mahmood, T.; Munawar, A.; Khalid, M.; Abbas, G. Synthesis, characterization and density functional theory study of some new 2-anilinothiazoles. J. Mol. Struct., 2014, 1072, 221-227.
[29]
Singh, N.; Sharma, U.S.; Sutar, N.; Kumar, S.; Sharma, U.K. Synthesis and antimicrobial activity of some novel 2-amino thiazole derivatives. J. Chem. Pharm. Res., 2010, 2(3), 691-698.
[30]
Mallia, C.J.; Englert, L.; Walter, G.C.; Baxendale, I.R. Thiazole formation through a modified Gewald reaction. Beilstein J. Org. Chem., 2015, 11, 875-883.
[31]
Samadhiya, P.; Sharma, R.; Srivastava, S.K.; Srivastava, S.D. Synthesis of 2-oxoazetidine derivatives of 2-aminothiazole and their biological activity. J. Serb. Chem. Soc., 2015, 77, 599-605.
[32]
Turan-Zitouni, G.; Altıntop, M.D.; Ozdemir, A.; Kaplancıklı, Z.A.; Çiftçi, G.A.; Temel, H.E. Synthesis and evaluation of Bis-thiazole derivatives as new anticancer agents. Eur. J. Med. Chem., 2016, 107, 288-294.
[33]
Qin, Y-J.; Wang, P-F.; Makawana, J.A.; Wang, Z-C.; Wang, Z. Yan-Gu.; Jiang, A.-Q.; Zhu, H.-L. Design, synthesis and biological evaluation of metronidazole-thiazole derivatives as antibacterial inhibitors bioorganic. Med. Chem. Lett., 2014, 24, 5279-5283.
[34]
Asif, M.; Ali, A.; Zafar, A.; Farhan, M.; Khanam, H.; Hadi, S.M. Shamsuzzaman. Microwave-assisted one pot synthesis, characterization, biological evaluation and molecular docking studies of steroidal thiazoles. Photochem. Photobiol., 2017, 166, 104-115.
[35]
Madhav, B.; Murthy, S.N. Anil kumar, B.S.P.; Ramesh, K.; Nageswar, Y.V.D. A tandem one-pot aqueous phase synthesis of thiazoles/selenazoles. Tetrahedron Lett., 2012, 53, 3835-3838.
[36]
Xiabing, M.; Ablajan, K.; Obul, M.; Seydimemet, M.; Ruzi, R.; Li, W. Facial one-pot, three-component synthesis of thiazole compounds by the reactions of aldehyde/ketone, thiosemicarbazide and chlorinated carboxylic ester derivatives. Tetrahedron, 2016, 72, 2349-2353.
[37]
Tsai, C.Y.; Kapoor, M.; Huang, Y.P.; Lin, H.; Liang, Y.C.; Lin, Y.L.; Huang, S.C.; Liao, W.N.; Chen, J.K.; Huang, J.S.; Hsu, M.H. Synthesis and evaluation of aminothiazole-paeonol derivatives as potential anticancer agents. Molecules, 2016, 21, 145.
[38]
Arunkumar, K.; Reddy, D.N.K.; Chandrasekhar, K.B.; Kumar, P.R.; Kumar, K.S.; Pal, M. Catalysis by zeolite leading to the construction of thiazole ring: An improved synthesis of 4-alkynyl substituted thiazoles. Tetrahedron Lett., 2012, 53, 3885-3889.
[39]
Gomez, J.D.C.; Balcazar, E.; Hagenbach, A.; Noufele, C.N.; Abram, U. Benzoylamido-substituted thiazoles and thiazolidines and their rhenium complexes. Polyhedron, 2016, 117, 293-299.
[40]
Yarovenko, V.N.; Polushina, A.V.; Zavarzin, I.V.; Krayushkin, M.M.; Kotovskaya, S.K.; Charushin, V.N. Synthesis of dihydrothiazoles and thiazoles based on monothiooxamides. J. Sulfur Chem., 2009, 30, 327-337.
[41]
Miura, T.; Funakoshi, Y.; Fujimoto, Y.; Nakahashi, J.; Murakami, M. Facile Synthesis of 2,5-Disubstituted thiazoles from terminal alkynes, sulfonyl azides, and thionoesters. Org. Lett., 2015, 17, 2454-2457.
[42]
Jeankumar, V.U.; Renuka, J.; Santosh, P.; Soni, V.; Sridevi, J.P.; Suryadevara, P.; Yogeeswari, P.; Sriram, D. Thiazole Aminopiperidine analogue: Design and synthesis of novel mycobacterium tuberculosis gyrb inhibitors. Eur. J. Med. Chem., 2013, 70, 143-153.
[43]
Mahesh, K.; Karpagam, S. Thiophene-Thiazole Functionalized Oligomers-Excellent fluorescent sensing and selective probe for copper and iron ion. Sens. Actuators, 2017, 251, 9-20.
[44]
Reddy, G.M.; Garcia, J.R.; Reddy, V.H.; Andrade, A.M.; Camilo, A. Junior, Ribeiro, R.A.P.; de Lazaro, S.R. Synthesis, antimicrobial activity and advances in Structure-Activity Relationships (SARs) of novel tri-substituted thiazole derivatives. Eur. J. Med. Chem., 2016, 123, 508-513.
[45]
Cheng, K.; Mcclory, A.; Walker, W. JieXu, Zhang, H.; Angelaud, R.; Gosselin, F. A Strecker approach to 2-substituted ethyl 5-aminothiazole-4-carboxylates. Tetrahedron Lett., 2016, 57(16), 1736-1738.
[46]
Sasmal, P.K.; Chandrasekhar, A.; Sridhar, S.; Iqbal, J. Novel one step method for conversion of isothiocyanates to 2-alkyl(aryl)aminothiazoles. Tetrahedron, 2008, 64, 11074-11080.
[47]
Aliança, A.S.d.S.; Oliveira, A.R.; Feitosa, A.P.S.; Ribeiro, K.R.C.; de Castro, M.C.A.B.; Leite, A.C.L.; Alves, L.C.; Brayner, F.A. In vitro evaluation of cytotoxicity and leishmanicidal activity of phthalimido-thiazole derivatives. Eur. J. Pharm. Sci., 2017, 105, 1-10.
[48]
Makam, P.; Kankanala, R.; Prakash, A.; Kannan, T. 2-(2-Hydrazinyl)thiazole derivatives: Design, synthesis and in vitro antimycobacterial studies. Eur. J. Med. Chem., 2013, 69, 564-576.
[49]
Koppireddi, S.; Chilaka, D.R.K.; Avula, S.; Komsani, J.R.; Kotamraju, S.; Yadla, R. Synthesis and Anticancer evaluation of 3-aryl-6-phenylimidazo [2,1-b]thiazoles. Bioorg. Med. Chem. Lett., 2014, 24, 5428-5431.
[50]
Park, J-H.; El-Gamal, M.I.; Lee, Y.S.; Oh, C-H. New imidazo [2,1-b]thiazole derivatives: Synthesis, in vitro anticancer evaluation and in silico studies. Eur. J. Med. Chem., 2011, 46, 5769-5777.
[51]
Chaniyara, R.; Tala, S.; Chen, C-W.; Lee, P-C.; Kakadiya, R.; Dong, H.; Marvania, B.; Chen, C-H.; Chou, T-C.; Lee, T-C.; Shah, A.; Su, T-L. Synthesis and antitumor evaluation of novel Benzo[d]pyrrolo [2,1-b]thiazole derivatives. Eur. J. Med. Chem., 2012, 53, 28-40.
[52]
Locatelli, A.; Cosconati, S.; Micucci, M.; Leoni, A.; Marinelli, L.; Bedini, A.; Ioan, P.; Spampinato, S.M.; Novellino, E.; Chiarini, A.; Budriesi, R. Ligand based approach to l-type calcium channel by imidazo [2,1-b]thiazole-1,4-Dihydropyridines: From heart activity to brain affinity. J. Med. Chem., 2013, 56, 3866-3877.
[53]
Lee, T.; Lee, D.; Lee, I.Y.; Gong, Y-D. Solid-Phase Synthesis of Thiazolo [4,5-b]pyridine Derivatives Using Friedländer Reaction. J. Comb. Chem., 2010, 12, 95-99.
[54]
Prajapati, N.P.; Vekariya, R.H.; Patel, H.D. Microwave Induced Facile One-pot Access to Diverse 2-cyanobenzothiazole-A Key Intermediate for the synthesis of firefly luciferin, 2015, 44, 81-89.
[55]
Srinivas, P.T.V.A.; Bhavani, S.; Rambabu, D.; Mandava, V.B.R.; Ravikumar, K.; Manojit, P. FeCl3/Ultrasound Mediated Reaction of 2-aminothiophenol with aldehydes in water: Synthesis of 2-substituted benzothiazoles of pharmacological interest. Lett. Drug Des. Discov., 2015, 12, 457-465. [56] Zhou, J.; Huang, X.; Zhang, Z.; Song, P.; Li, Y. Trypsin-catalyzed multicomponent reaction: A novel and efficient one-pot synthesis of thiazole-2-imine derivatives. J. Biotechnol., 2017, 241, 14-21.
[56]
Zhou, J.; Huang, X.; Zhang, Z.; Song, P.; Li, Y. Trypsin-catalyzed multicomponent reaction: A novel and efficient one-pot synthesis of thiazole-2-imine derivatives. J. Biotechnol., 2017, 241, 14-21.
[57]
Shiran, J.A.; Yahyazadeh, A.; Mamaghani, M.; Yamin, B.M.; Albadi, J.; Shirini, F.; Rassa, M. Novel, One-Pot, Three-Component, regioselective synthesis of fluorinecontaining thiazole and bis-3h-thiazole derivatives using polyvinyl pyridine as heterogeneous catalyst, and evaluation of their antibacterial activity. Synth. Commun., 2015, 45, 1520-1532.
[58]
Grange, J.M.; Zumla, A. The global emergency of tuberculosis: what is the cause? J. R. Soc. Health, 2002, 122, 78-81.
[59]
Bera, P.; Brandão, P.; Mondal, G.; Jana, H.; Jana, A.; Santra, A.; Bera, P. Synthesis of a new pyridinyl thiazole ligand with hydrazone moiety and its cobalt(III) complex: X-ray crystallography, in vitro evaluation of antibacterial activity. Polyhedron, 2017, 134, 230-237.
[60]
Bharti, S.K.; Nath, G.; Tilak, R.; Singh, S.K. Synthesis, anti-bacterial and anti-fungal activities of some novel Schiff bases containing 2,4-disubstituted thiazole ring. Eur. J. Med. Chem., 2010, 45, 651-660.
[61]
Bondock, S.; Naser, T.; Ammar, Y.A. Synthesis of some new 2-(3-pyridyl)-4,5-disubstituted thiazoles as potent antimicrobial agents. Eur. J. Med. Chem., 2013, 62, 270-279.
[62]
Nastasa, C.; Tiperciuc, B.; Duma, M.; Benedec, D.; Oniga, O. New hydrazones bearing thiazole scaffold: synthesis, characterization, antimicrobial, and antioxidant investigation. Molecules, 2015, 20, 17325-17338.
[63]
Liaras, K.; Geronikaki, A.; Glamoclija, J.; Ciric, A.; Sokovic, M. Thiazole-based chalcones as potent antimicrobial agents. Synthesis and biological evaluation. Bioorg. Med. Chem., 2011, 19, 3135-3140.
[64]
Mohammadi-Farani, A.; Foroumadi, A.; Rezvani Kashani, M.; Aliabadi, A. N-Phenyl-2-p-tolylthiazole-4-carboxamide derivatives: Synthesis and cytotoxicity evaluation as anticancer agents. Iran. J. Basic Med. Sci., 2014, 17, 502-508.
[65]
Parrino, B.; Attanzio, A.; Spano, V.; Cascioferro, S.; Montalbano, A.; Barraja, P.; Tesoriere, L.; Diana, P.; Cirrincione, G.; Carbone, A. Synthesis, antitumor activity and CDK1 inhibiton of new thiazole nortopsentin analogues. Eur. J. Med. Chem., 2017, 138, 371-383.
[66]
Wilson, K.J.; Illig, C.R.; Subasinghe, N.; Hoffman, J.B.; Rudolph, M.J.; Soll, R. Synthesis of thiophene-2-carboxamidines containing 2-amino-thiazoles and their biological evaluation as urokinase inhibitors. Bioorg. Med. Chem. Lett., 2001, 11, 915-918.
[67]
Popsavin, M.; Spaic, S.; Svirčev, M. Kojić, v.; Bogdanović, G.; Popsavin, V. 2-(3-Amino-3-deoxy-β-d-xylofuranosyl)thiazole-4-carboxamide: A new tiazofurin analogue with potent antitumour activity. Bioorg. Med. Chem. Lett., 2006, 16, 5317-5320.
[68]
Gomha, S.M.; Kheder, N.A.; Abdelaziz, M.R.; Mabkhot, Y.N.; Alhajoj, A.M. A facile synthesis and anticancer activity of some novel thiazoles carrying 1,3,4-thiadiazole moiety. Chem. Cent. J., 2017, 11, 25.
[69]
Hassan, G.S.; El-Messery, S.M.; Al-Omary, F.A.M.; El-Subbagh, H.I. Substituted thiazole Synthesis and Antitumour activity of certain 2-(substituted amino)-4-phenyl-1,3-thiazole analogue. Bioorg. Med. Chem. Lett., 2012, 54, 6318-6323.
[70]
Lu, X.; Liu, X.; Wan, B.; Franzblau, S.G.; Chen, L.; Zhou, C.; You, Q. Synthesis and evaluation of anti-tubercular and antibacterial activities of new 4-(2,6-dichlorobenzyloxy)phenyl thiazole, oxazole and imidazole derivatives. Part 2. Eur. J. Med. Chem., 2012, 49, 164-171.
[71]
Dawood, K.M.; Eldebss, T.M.A.; El-Zahabi, H.S.M.; Yousef, M.H. Synthesis and antiviral activity of some new bis-1,3-thiazole derivatives. Eur. J. Med. Chem., 2015, 102, 266-276.
[72]
Curreli, F.; Choudhury, S.; Pyatkin, I.; Zagorodnikov, V.P.; Bulay, A.K.; Altieri, A.; Do Kwon, Y.; Kwong, P.D.; Debnath, A.K. Design, synthesis and antiviral activity of entry inhibitors that target the CD4-binding site of HIV-1. J. Med. Chem., 2012, 55, 4764-4775.
[73]
Grozav, A.; Porumb, I.D.; Ga˘ina, L.I.; Filip, L.; Hanganu, D. Cytotoxicity and Antioxidant Potential of Novel 2-(2-((1H-indol-5yl)methylene)-hydrazinyl)-thiazole Derivatives. Molecules, 2017, 22, 260.
[74]
Jaishree, V.; Ramdas, N.; Sachin, J.; Ramesh, B. Invitro antioxidant property of new thiazole derivatives. J. Saudi Chem. Soc., 2012, 16, 371-376.
[75]
Reddy, M.V.B.; Srinivasulu, D.; Peddanna, K.; Apparao, C.; Ramesh, P. Synthesis and antioxidant activity of new thiazole analogues possessing urea, thiourea, and selenourea functionality. Synth. Commun., 2015, 45, 2592-2600.
[76]
Fadda, A.A.; Berghot, M.A.; Amer, F.A.; Badawy, D.S.; Bayoumy, N.M. Synthesis and antioxidant and antitumor activity of novel pyridine, chromene, thiophene and thiazole derivatives. Arch. Pharm. Chem. Life Sci, 2011, 1-8.

Rights & Permissions Print Cite
© 2024 Bentham Science Publishers | Privacy Policy