摘要
背景:咪唑并[2,1-b]噻唑,一种著名的稠合五元杂环,是药物化学领域最有前途和用途最广泛的部分之一。 已对咪唑并[2,1-b]噻唑的衍生物进行了研究,以开发具有多种药理活性的新衍生物。 该稠合的杂环也是许多治疗剂的一部分。 目的:综述咪唑并[2,1-b]噻唑衍生物及其在2000-2018年间开发的新分子的广泛药理活性及其实用性。 方法:对所有相关论文和专利进行了详尽的文献综述。 结论:本综述涵盖了多个方面,有望为基于咪唑并[2,1-b]噻唑的化合物的设计提供有用的见识,并会激发药物化学家获得全面且面向目标的信息,以实现这一目标。 在临床上可行的候选药物开发方面的重大突破。
关键词: 咪唑并[2
[1]
(a) Akhtar, W.; Khan, M.F.; Verma, G.; Shaquiquzzaman, M.; Rizvi, M.A.; Mehdi, S.H.; Akhter, M.; Alam, M.M. Therapeutic evolution of benzimidazole derivatives in the last quinquennial period. Eur. J. Med. Chem, 2017, 126, 705-753.
[http://dx.doi.org/10.1016/j.ejmech.2016.12.010] [PMID: 27951484]
(b) Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications of the Most Relevant APIs, 3rd ed; , 1999.
[http://dx.doi.org/10.1016/j.ejmech.2016.12.010] [PMID: 27951484]
(b) Kleeman, A.; Engel, J.; Kutscher, B.; Reichert, D. Pharmaceutical Substances: Syntheses, Patents, Applications of the Most Relevant APIs, 3rd ed; , 1999.
[2]
Fenichel, R.I.; Chirigos, M.A.; Hoerig, C.H. Immune modulation agents and their mechanism, 1984, 383-408.
[3]
Fascio, M.L.; Errea, M.I.; D’Accorso, N.B. Imidazothiazole and related heterocyclic systems. Synthesis, chemical and biological properties. Eur. J. Med. Chem., 2015, 90, 666-683.
[http://dx.doi.org/10.1016/j.ejmech.2014.12.012] [PMID: 25499987]
[http://dx.doi.org/10.1016/j.ejmech.2014.12.012] [PMID: 25499987]
[4]
Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M. Imidazo[2,1-b] thiazole: introduction, current and perspective. Bioenergetics, 2017, 6, 1-3.
[http://dx.doi.org/10.4172/2167-7662.1000151]
[http://dx.doi.org/10.4172/2167-7662.1000151]
[5]
Kamal, A.; Khanna, G.B.R.; Krishnaji, T.; Ramu, R. A new facile chemoenzymatic synthesis of levamisole. Bioorg. Med. Chem. Lett., 2005, 15(3), 613-615.
[http://dx.doi.org/10.1016/j.bmcl.2004.11.054] [PMID: 15664823]
[http://dx.doi.org/10.1016/j.bmcl.2004.11.054] [PMID: 15664823]
[6]
Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M. Novel thiazole derivatives: a patent review (2008 - 2012; Part 1). Expert Opin. Ther. Pat., 2014, 24(2), 201-216.
[http://dx.doi.org/10.1517/13543776.2014.858121] [PMID: 24215328]
[http://dx.doi.org/10.1517/13543776.2014.858121] [PMID: 24215328]
[7]
Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M. Novel thiazole derivatives: a patent review (2008 - 2012. Part 2). Expert Opin. Ther. Pat., 2014, 24(7), 759-777.
[http://dx.doi.org/10.1517/13543776.2014.910196] [PMID: 24745553]
[http://dx.doi.org/10.1517/13543776.2014.910196] [PMID: 24745553]
[8]
Alexander, R.P.; Ali, M.H.; Brown, J.A.; Jackson, V.E. Imidazothiazole derivative as modulators of TNF activity. Patent No. WO 2015086504 A1,, 2015.
[9]
Kamal, A.; Dudekula, D.; Jonnala, S.R.; Earla, V.B. Imidazothiazole-chalcone derivatives as potential anticancer agents and process for the preparation thereof. Patent No. US 8,916,711 B2, 2014.
[10]
Mueller, K.H.; Schwarz, H.G.; Ilg, K.; Voerste, A.; Malsam, O.; Portz, D.; Jeschke, P. Imidazothiazole sulfonamides as nematicides. Patent No. US 9,512,144 B2,, 2016.
[11]
Mas, P.J.; Torrens, J.A. Substituted N-imidazo[2,1- b]thiazole-5-sulfonamide derivatives as 5-HT6 ligands. Patent No. US 20110105555A1, 2011.
[12]
Ashwell, M.A.; Tandon, M.; Lapierre, J.M. Synthesis of imidazooxazole and imidazothiazole inhibitors of P38 MAP kinase. Patent No. US 8,178,672 B2,, 2012.
[13]
Wynne, G.M.; Wren, S.P.; Price, P.D. Compounds for treating duchenne muscular dystrophy. Patent No. WO 2009013477A1, 2009.
[14]
Bemis, J.; Disch, J.S. Sirtuin modulating imidazothiazole compounds. Sirtris Pharmaceuticals Inc. Patent No. WO 2008156866A1, 2008.
[15]
Kawato, H.; Miyazaki, M.; Naito, H. Imidazothiazole derivatives. Patent No. US 20090312310A1, 2009.
[17]
Zoller, G.; Strobel, H.; Will, D. Imidazo[2,1-b]thiazoles and their use as pharmaceuticals. Patent No. WO 2008058641, 2008.
[18]
Active Biotech, A.B. Imidazo[2,1-b]thiazole and 5,6- dihydroimidazo[2,1-b]thiazole derivatives useful as s100- inhibitors. Patent No. US 20180282348A1 2018.
[19]
Borhani, D.W.; Calderwood, D.J.; Frank, K.E.; Davis, H.M.; Josephsohn, N.S.; Skinner, B.S. Novel imidazothiazoles and imidazoxazoles. Patent No.WO WO/2008/06328, 2008.
[20]
Moser, R.E.; Powers, L.J.; Ariyan, Z.S. Anti-inflammatory imidazothiazoles. Patent. No . US 4041167A, 1976.
[21]
Nishio, K.; Chiyomaru, I.; Anma, K.; Yamamoto, K.; Ohno, H.; Takayanagi, N. 2,3-Di-substituted-5,6-dihydroimidazo[2,1-b] thiazole, its salts, production thereof and anti-inflammatory agent containing the same. Patent. No. US 4556669A, 1985. 1985.
[22]
Barba, O.; Dawson, G.J.; Krulle, T.M.; Rowley, R.J.; Smyth, D.; Thomas, G.H. Dihydroimidazothiazole derivatives. Patent No. US 20090221645A1, 2009.
[23]
Chen, W.; Zheng, R.; Baade, P.D.; Zhang, S.; Zeng, H.; Bray, F.; Jemal, A.; Yu, X.Q.; He, J. Cancer statistics in China, 2015. CA Cancer J. Clin., 2016, 66(2), 115-132.
[http://dx.doi.org/10.3322/caac.21338] [PMID: 26808342]
[http://dx.doi.org/10.3322/caac.21338] [PMID: 26808342]
[24]
Lippert, T.H.; Ruoff, H.J.; Volm, M. Could a revision of the current guidelines for cancer drug use improve the quality of cancer treatment? Ther. Clin. Risk Manag., 2014, 10, 69-72.
[http://dx.doi.org/10.2147/TCRM.S51404] [PMID: 24511236]
[http://dx.doi.org/10.2147/TCRM.S51404] [PMID: 24511236]
[25]
Andreani, A.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Recanatini, M.; Garaliene, V. Potential antitumor agents. Part 29(1): synthesis and potential coanthracyclinic activity of imidazo[2,1-b]thiazole guanylhydrazones. Bioorg. Med. Chem., 2000, 8(9), 2359-2366.
[http://dx.doi.org/10.1016/S0968-0896(00)00165-6] [PMID: 11026549]
[http://dx.doi.org/10.1016/S0968-0896(00)00165-6] [PMID: 11026549]
[26]
Ali, A.R.; El-Bendary, E.R.; Ghaly, M.A.; Shehata, I.A. Synthesis, in vitro anticancer evaluation and in silico studies of novel imidazo[2,1-b]thiazole derivatives bearing pyrazole moieties. Eur. J. Med. Chem., 2014, 75, 492-500.
[http://dx.doi.org/10.1016/j.ejmech.2013.12.010] [PMID: 24576591]
[http://dx.doi.org/10.1016/j.ejmech.2013.12.010] [PMID: 24576591]
[27]
Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Garaliene, V.; Welsh, W.; Arora, S.; Farruggia, G.; Masotti, L. Antitumor activity of new substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and study of their effect on the cell cycle. J. Med. Chem., 2005, 48(17), 5604-5607.
[http://dx.doi.org/10.1021/jm050353e] [PMID: 16107161]
[http://dx.doi.org/10.1021/jm050353e] [PMID: 16107161]
[28]
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(12), 5769-5777.
[http://dx.doi.org/10.1016/j.ejmech.2011.08.024] [PMID: 22033063]
[http://dx.doi.org/10.1016/j.ejmech.2011.08.024] [PMID: 22033063]
[29]
Gürsoy, E.; Güzeldemirci, N.U. Synthesis and primary cytotoxicity evaluation of new imidazo[2,1-b]thiazole derivatives. Eur. J. Med. Chem., 2007, 42(3), 320-326.
[http://dx.doi.org/10.1016/j.ejmech.2006.10.012] [PMID: 17145120]
[http://dx.doi.org/10.1016/j.ejmech.2006.10.012] [PMID: 17145120]
[30]
Koppireddi, S.; Chilaka, D.R.; 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(23), 5428-5431.
[http://dx.doi.org/10.1016/j.bmcl.2014.10.030] [PMID: 25453802]
[http://dx.doi.org/10.1016/j.bmcl.2014.10.030] [PMID: 25453802]
[31]
Romagnoli, R.; Baraldi, P.G.; Prencipe, F.; Balzarini, J.; Liekens, S.; Estévez, F. Design, synthesis and antiproliferative activity of novel heterobivalent hybrids based on imidazo[2,1-b][1,3,4]thiadiazole and imidazo[2,1-b][1,3] thiazole scaffolds. Eur. J. Med. Chem., 2015, 101, 205-217.
[http://dx.doi.org/10.1016/j.ejmech.2015.06.042] [PMID: 26141911]
[http://dx.doi.org/10.1016/j.ejmech.2015.06.042] [PMID: 26141911]
[32]
Mahindroo, N.; Liou, J.P.; Chang, J.Y.; Hsieh, H.P. Antitubulin agents for the treatment of cancer - a medicinal chemistry update. Expert Opin. Ther. Pat., 2006, 16, 647-691.
[http://dx.doi.org/10.1517/13543776.16.5.647]
[http://dx.doi.org/10.1517/13543776.16.5.647]
[33]
Li, L.; Jiang, S.; Li, X.; Liu, Y.; Su, J.; Chen, J. Recent advances in trimethoxyphenyl (TMP) based tubulin inhibitors targeting the colchicine binding site. Eur. J. Med. Chem., 2018, 151, 482-494.
[http://dx.doi.org/10.1016/j.ejmech.2018.04.011] [PMID: 29649743]
[http://dx.doi.org/10.1016/j.ejmech.2018.04.011] [PMID: 29649743]
[34]
Kamal, A.; Dastagiri, D.; Ramaiah, M.J.; Reddy, J.S.; Bharathi, E.V.; Srinivas, C.; Pushpavalli, S.N.; Pal, D.; Pal-Bhadra, M. Synthesis of imidazothiazole-chalcone derivatives as anticancer and apoptosis inducing agents. ChemMedChem, 2010, 5(11), 1937-1947.
[http://dx.doi.org/10.1002/cmdc.201000346] [PMID: 20836120]
[http://dx.doi.org/10.1002/cmdc.201000346] [PMID: 20836120]
[35]
Kamal, A.; Kashi Reddy, M.; Viswanath, A. The design and development of imidazothiazole-chalcone derivatives as potential anticancer drugs. Expert Opin. Drug Discov., 2013, 8(3), 289-304.
[http://dx.doi.org/10.1517/17460441.2013.758630] [PMID: 23317445]
[http://dx.doi.org/10.1517/17460441.2013.758630] [PMID: 23317445]
[36]
Kamal, A.; Balakrishna, M.; Nayak, V.L.; Shaik, T.B.; Faazil, S.; Nimbarte, V.D. Design and synthesis of imidazo[2,1-b]thiazole-chalcone conjugates: microtubule-destabilizing agents. ChemMedChem, 2014, 9(12), 2766-2780.
[http://dx.doi.org/10.1002/cmdc.201402310] [PMID: 25313981]
[http://dx.doi.org/10.1002/cmdc.201402310] [PMID: 25313981]
[37]
Sayeed, I.B.; Garikapati, K.R.; Makani, V.K.K.; Nagarajan, A.; Shareef, M.A.; Alarifi, A.; Pal-Bhadra, M.; Kamal, A. Development and biological evaluation of imidazothiazole propenones as tubulin inhibitors that effectively triggered apoptotic cell death in alveolar lung cancer cell. ChemistrySelect, 2017, 2, 6480-6487.
[http://dx.doi.org/10.1002/slct.201701563]
[http://dx.doi.org/10.1002/slct.201701563]
[38]
Shaik, S.P.; Nayak, V.L.; Sultana, F.; Rao, A.V.S.; Shaik, A.B.; Babu, K.S.; Kamal, A. Design and synthesis of imidazo[2,1-b]thiazole linked triazole conjugates: microtubule-destabilizing agents. Eur. J. Med. Chem., 2017, 126, 36-51.
[http://dx.doi.org/10.1016/j.ejmech.2016.09.060] [PMID: 27744185]
[http://dx.doi.org/10.1016/j.ejmech.2016.09.060] [PMID: 27744185]
[39]
Baig, M.F.; Nayak, V.L.; Budaganaboyina, P.; Mullagiri, K.; Sunkari, S.; Gour, J.; Kamal, A. Synthesis and biological evaluation of imidazo[2,1-b]thiazole-benzimidazole conjugates as microtubule-targeting agents. Bioorg. Chem., 2018, 77, 515-526.
[http://dx.doi.org/10.1016/j.bioorg.2018.02.005] [PMID: 29459129]
[http://dx.doi.org/10.1016/j.bioorg.2018.02.005] [PMID: 29459129]
[40]
Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Farruggia, G.; Stefanelli, C.; Masotti, L.; Kunkel, M.W. Synthesis and antitumor activity of guanylhydrazones from 6-(2,4-dichloro-5-nitrophenyl)imidazo[2,1-b]thiazoles and 6-pyridylimidazo[2,1-b]thiazoles(1). J. Med. Chem., 2006, 49(26), 7897-7901.
[http://dx.doi.org/10.1021/jm061077m] [PMID: 17181173]
[http://dx.doi.org/10.1021/jm061077m] [PMID: 17181173]
[41]
Andreani, A.; Granaiola, M.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Calonghi, N.; Cappadone, C.; Farruggia, G.; Stefanelli, C.; Masotti, L.; Nguyen, T.L.; Hamel, E.; Shoemaker, R.H. Substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indolinones and analogues: synthesis, cytotoxic activity, and study of the mechanism of action. J. Med. Chem., 2012, 55(5), 2078-2088.
[http://dx.doi.org/10.1021/jm2012694] [PMID: 22283430]
[http://dx.doi.org/10.1021/jm2012694] [PMID: 22283430]
[42]
Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Calonghi, N.; Cappadone, C.; Farruggia, G.; Zini, M.; Stefanelli, C.; Masotti, L.; Radin, N.S.; Shoemaker, R.H. New antitumor imidazo[2,1-b]thiazole guanylhydrazones and analogues. J. Med. Chem., 2008, 51(4), 809-816.
[http://dx.doi.org/10.1021/jm701246g] [PMID: 18251494]
[http://dx.doi.org/10.1021/jm701246g] [PMID: 18251494]
[43]
Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Calonghi, N.; Cappadone, C.; Voltattorni, M.; Zini, M.; Stefanelli, C.; Masotti, L.; Shoemaker, R.H. Antitumor activity of new substituted 3-(5-imidazo[2,1-b]thiazolylmethylene)-2-indo-linones and 3-(5-imidazo[2,1-b]thiadiazolylmethylene)-2-indolinones: selectivity against colon tumor cells and effect on cell cycle-related events. J. Med. Chem., 2008, 51(23), 7508-7513.
[http://dx.doi.org/10.1021/jm800827q] [PMID: 19006285]
[http://dx.doi.org/10.1021/jm800827q] [PMID: 19006285]
[44]
Ferguson, F.M.; Gray, N.S. Kinase inhibitors: the road ahead. Nat. Rev. Drug Discov., 2018, 17(5), 353-377.
[http://dx.doi.org/10.1038/nrd.2018.21] [PMID: 29545548]
[http://dx.doi.org/10.1038/nrd.2018.21] [PMID: 29545548]
[45]
Gross, S.; Rahal, R.; Stransky, N.; Lengauer, C.; Hoeflich, K.P. Targeting cancer with kinase inhibitors. J. Clin. Invest., 2015, 125(5), 1780-1789.
[http://dx.doi.org/10.1172/JCI76094] [PMID: 25932675]
[http://dx.doi.org/10.1172/JCI76094] [PMID: 25932675]
[46]
Karoulia, Z.; Gavathiotis, E.; Poulikakos, P.I. New perspectives for targeting RAF kinase in human cancer. Nat. Rev. Cancer, 2017, 17(11), 676-691.
[http://dx.doi.org/10.1038/nrc.2017.79] [PMID: 28984291]
[http://dx.doi.org/10.1038/nrc.2017.79] [PMID: 28984291]
[47]
Abdel-Maksoud, M.S.; Kim, M.R.; El-Gamal, M.I.; Gamal El-Din, M.M.; Tae, J.; Choi, H.S.; Lee, K.T.; Yoo, K.H.; Oh, C.H. Design, synthesis, in vitro antiproliferative evaluation, and kinase inhibitory effects of a new series of imidazo[2,1-b]thiazole derivatives. Eur. J. Med. Chem., 2015, 95, 453-463.
[http://dx.doi.org/10.1016/j.ejmech.2015.03.065] [PMID: 25841200]
[http://dx.doi.org/10.1016/j.ejmech.2015.03.065] [PMID: 25841200]
[48]
Malumbres, M.; Barbacid, M. Cell cycle, CDKs and cancer: a changing paradigm. Nat. Rev. Cancer, 2009, 9(3), 153-166.
[http://dx.doi.org/10.1038/nrc2602] [PMID: 19238148]
[http://dx.doi.org/10.1038/nrc2602] [PMID: 19238148]
[49]
Bertoli, C.; Skotheim, J.M.; de Bruin, R.A. Control of cell cycle transcription during G1 and S phases. Nat. Rev. Mol. Cell Biol., 2013, 14(8), 518-528.
[http://dx.doi.org/10.1038/nrm3629] [PMID: 23877564]
[http://dx.doi.org/10.1038/nrm3629] [PMID: 23877564]
[50]
Andreani, A.; Cavalli, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Recanatini, M.; Garnier, M.; Meijer, L. Imidazo[2,1 -b]thiazolylmethylene- and indolylmethylene-2-indolinones: a new class of cyclin-dependent kinase inhibitors. Design, synthesis, and CDK1/cyclin B inhibition. Anticancer Drug Des., 2000, 15(6), 447-452.
[PMID: 11716438]
[PMID: 11716438]
[51]
Yap, J.L.; Worlikar, S.; MacKerell, A.D., Jr; Shapiro, P.; Fletcher, S. Small-molecule inhibitors of the ERK signaling pathway: towards novel anticancer therapeutics. ChemMedChem, 2011, 6(1), 38-48.
[http://dx.doi.org/10.1002/cmdc.201000354] [PMID: 21110380]
[http://dx.doi.org/10.1002/cmdc.201000354] [PMID: 21110380]
[52]
Li, L.; Zhao, G.D.; Shi, Z.; Qi, L.L.; Zhou, L.Y.; Fu, Z.X. The Ras/Raf/MEK/ERK signaling pathway and its role in the occurrence and development of HCC. Oncol. Lett., 2016, 12(5), 3045-3050.
[http://dx.doi.org/10.3892/ol.2016.5110] [PMID: 27899961]
[http://dx.doi.org/10.3892/ol.2016.5110] [PMID: 27899961]
[53]
Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Lannigan, D.; Smith, J.; Scudiero, D.; Kondapaka, S.; Shoemaker, R.H. Imidazo[2,1-b]thiazole guanylhydrazones as RSK2 inhibitors. Eur. J. Med. Chem., 2011, 46(9), 4311-4323.
[http://dx.doi.org/10.1016/j.ejmech.2011.07.001] [PMID: 21794960]
[http://dx.doi.org/10.1016/j.ejmech.2011.07.001] [PMID: 21794960]
[54]
Fidanze, S.D.; Erickson, S.A.; Wang, G.T.; Mantei, R.; Clark, R.F.; Sorensen, B.K.; Bamaung, N.Y.; Kovar, P.; Johnson, E.F.; Swinger, K.K.; Stewart, K.D.; Zhang, Q.; Tucker, L.A.; Pappano, W.N.; Wilsbacher, J.L.; Wang, J.; Sheppard, G.S.; Bell, R.L.; Davidsen, S.K.; Hubbard, R.D. Imidazo[2,1-b]thiazoles: multitargeted inhibitors of both the insulin-like growth factor receptor and members of the epidermal growth factor family of receptor tyrosine kinases. Bioorg. Med. Chem. Lett., 2010, 20(8), 2452-2455.
[http://dx.doi.org/10.1016/j.bmcl.2010.03.015] [PMID: 20346655]
[http://dx.doi.org/10.1016/j.bmcl.2010.03.015] [PMID: 20346655]
[55]
Morris, B.J. Seven sirtuins for seven deadly diseases of aging. Free Radic. Biol. Med., 2013, 56, 133-171.
[http://dx.doi.org/10.1016/j.freeradbiomed.2012.10.525] [PMID: 23104101]
[http://dx.doi.org/10.1016/j.freeradbiomed.2012.10.525] [PMID: 23104101]
[56]
Hu, J.; Jing, H.; Lin, H. Sirtuin inhibitors as anticancer agents. Future Med. Chem., 2014, 6(8), 945-966.
[http://dx.doi.org/10.4155/fmc.14.44] [PMID: 24962284]
[http://dx.doi.org/10.4155/fmc.14.44] [PMID: 24962284]
[57]
Vu, C.B.; Bemis, J.E.; Disch, J.S.; Ng, P.Y.; Nunes, J.J.; Milne, J.C.; Carney, D.P.; Lynch, A.V.; Smith, J.J.; Lavu, S.; Lambert, P.D.; Gagne, D.J.; Jirousek, M.R.; Schenk, S.; Olefsky, J.M.; Perni, R.B. Discovery of imidazo[1,2-b]thiazole derivatives as novel SIRT1 activators. J. Med. Chem., 2009, 52(5), 1275-1283.
[http://dx.doi.org/10.1021/jm8012954] [PMID: 19199480]
[http://dx.doi.org/10.1021/jm8012954] [PMID: 19199480]
[58]
Ding, H.; Chen, Z.; Zhang, C.; Xin, T.; Wang, Y.; Song, H.; Jiang, Y.; Chen, Y.; Xu, Y.; Tan, C. Synthesis and cytotoxic activity of some novel N-pyridinyl-2-(6-phenylimidazo[2,1-b]thiazol-3-yl)acetamide derivatives. Molecules, 2012, 17(4), 4703-4716.
[http://dx.doi.org/10.3390/molecules17044703] [PMID: 22525437]
[http://dx.doi.org/10.3390/molecules17044703] [PMID: 22525437]
[59]
Andreani, A.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Cervellati, R.; Greco, E.; Kondratyuk, T.P.; Park, E.J.; Huang, K.; van Breemen, R.B.; Pezzuto, J.M. Chemopreventive and antioxidant activity of 6-substituted imidazo[2,1-b]thiazoles. Eur. J. Med. Chem., 2013, 68, 412-421.
[http://dx.doi.org/10.1016/j.ejmech.2013.07.052] [PMID: 23994869]
[http://dx.doi.org/10.1016/j.ejmech.2013.07.052] [PMID: 23994869]
[60]
Berman, E.M.; Werbel, L.M. The renewed potential for folate antagonists in contemporary cancer chemotherapy. J. Med. Chem., 1991, 34(2), 479-485.
[http://dx.doi.org/10.1021/jm00106a001] [PMID: 1995868]
[http://dx.doi.org/10.1021/jm00106a001] [PMID: 1995868]
[61]
Gangjee, A.; Shi, J.; Queener, S.F. Synthesis and biological activities of conformationally restricted, tricyclic nonclassical antifolates as inhibitors of dihydrofolate reductases. J. Med. Chem., 1997, 40(12), 1930-1936.
[http://dx.doi.org/10.1021/jm960693n] [PMID: 9191971]
[http://dx.doi.org/10.1021/jm960693n] [PMID: 9191971]
[62]
Ewida, M.A.; Abou El Ella, D.A.; Lasheen, D.S.; Ewida, H.A.; El-Gazzar, Y.I.; El-Subbagh, H.I. Imidazo[2′,1′:2,3]thiazolo[4,5-d]pyridazinone as a new scaffold of DHFR inhibitors: synthesis, biological evaluation and molecular modeling study. Bioorg. Chem., 2018, 80, 11-23.
[http://dx.doi.org/10.1016/j.bioorg.2018.05.025] [PMID: 29864684]
[http://dx.doi.org/10.1016/j.bioorg.2018.05.025] [PMID: 29864684]
[63]
Wise, R. BSAC working party on the urgent need: regenerating antibacterial drug discovery and development. The urgent need for new antibacterial agents. J. Antimicrob. Chemother., 2011, 66(9), 1939-1940.
[http://dx.doi.org/10.1093/jac/dkr261] [PMID: 21700627]
[http://dx.doi.org/10.1093/jac/dkr261] [PMID: 21700627]
[64]
Payne, D.J.; Gwynn, M.N.; Holmes, D.J.; Pompliano, D.L. Drugs for bad bugs: confronting the challenges of antibacterial discovery. Nat. Rev. Drug Discov., 2007, 6(1), 29-40.
[http://dx.doi.org/10.1038/nrd2201] [PMID: 17159923]
[http://dx.doi.org/10.1038/nrd2201] [PMID: 17159923]
[65]
Dangi, R.R.; Hussain, N.; Talesara, G.L. Synthesis characterization and biological evaluation of some alkoxyphthalimide derivatives of 3-(4-substituted phenyl)-6,6- diphenyl-3,3a-dihydro-2 H -imidazo[2,1- b]pyrazolo[3,4- d][1,3]thiazol-7(6 H)-one. Med. Chem. Res., 2011, 20, 1490-1498.
[http://dx.doi.org/10.1007/s00044-010-9392-4]
[http://dx.doi.org/10.1007/s00044-010-9392-4]
[66]
Robert, F.; Boukraa, S.; Panouse, J.J.; Loppinet, V.; Chaumont, J.P. Derivatives of the imidazo[2,1-b]thiazoles X. Fungistatic properties of 2-aminothiazoles and 6- arylimidazo[2,1-b]-thiazoles respectively substituted in 4 and in 3 by arylethyl, aroylmethyl, β-hydroxy β-arylethyl and ethoxycarbonylmethyl groups. Eur. J. Med. Chem., 1990, 25, 731-736.
[http://dx.doi.org/10.1016/0223-5234(90)90192-6]
[http://dx.doi.org/10.1016/0223-5234(90)90192-6]
[67]
Amarouch, H.; Loiseau, P.R.; Bacha, C.; Caujolle, R.; Payard, M.; Loiseau, P.M.; Bories, C.; Gayral, P. Imidazo[2,1-b]thiazoles: analogues of levamisole. Eur. J. Med. Chem., 1987, 22, 463-466.
[http://dx.doi.org/10.1016/0223-5234(87)90037-7]
[http://dx.doi.org/10.1016/0223-5234(87)90037-7]
[68]
Güzeldemirci, N.U.; Küçükbasmaci, O. Synthesis and antimicrobial activity evaluation of new 1,2,4-triazoles and 1,3,4-thiadiazoles bearing imidazo[2,1-b]thiazole moiety. Eur. J. Med. Chem., 2010, 45(1), 63-68.
[http://dx.doi.org/10.1016/j.ejmech.2009.09.024] [PMID: 19939519]
[http://dx.doi.org/10.1016/j.ejmech.2009.09.024] [PMID: 19939519]
[69]
Abdel-Wahab, B.F.; Khidre, R.E.; Awad, G.E.A. Design and synthesis of novel 6- (5-Methyl-1H-1,2,3-triazol-4-yl)-5-[(2-(thiazol-2yl)hydrazono)methyl]imidazo[2,1- b]thiazoles as antimicrobial agents. J. Heterocycl. Chem., 2016, 54, 489-494.
[http://dx.doi.org/10.1002/jhet.2610]
[http://dx.doi.org/10.1002/jhet.2610]
[70]
Juspin, T.; Laget, M.; Terme, T.; Azas, N.; Vanelle, P. TDAE-assisted synthesis of new imidazo[2,1-b]thiazole derivatives as anti-infectious agents. Eur. J. Med. Chem., 2010, 45(2), 840-845.
[http://dx.doi.org/10.1016/j.ejmech.2009.10.048] [PMID: 19939516]
[http://dx.doi.org/10.1016/j.ejmech.2009.10.048] [PMID: 19939516]
[71]
Maruyama, T.; Kano, Y.; Yamamoto, Y.; Kurazono, M.; Iwamatsu, K.; Atsumi, K.; Shitara, E. Synthesis and SAR study of novel 7-(pyridinium-3-yl)-carbonyl imidazo[5,1-b]thiazol-2-yl carbapenems. Bioorg. Med. Chem., 2007, 15(1), 392-402.
[http://dx.doi.org/10.1016/j.bmc.2006.09.049] [PMID: 17055731]
[http://dx.doi.org/10.1016/j.bmc.2006.09.049] [PMID: 17055731]
[72]
Li, Y.; Bionda, N.; Fleeman, R.; Wang, H.; Ozawa, A.; Houghten, R.A.; Shaw, L. Identification of 5,6-dihydroimidazo[2,1-b]thiazoles as a new class of antimicrobial agents. Bioorg. Med. Chem., 2016, 24(21), 5633-5638.
[http://dx.doi.org/10.1016/j.bmc.2016.09.027] [PMID: 27663549]
[http://dx.doi.org/10.1016/j.bmc.2016.09.027] [PMID: 27663549]
[73]
Güzeldemirci, N.U.; Şatana, D.; Kucukbasmaci, O. Synthesis and antimicrobial evaluation of some new hydrazone derivatives of 6-(4-nitrophenyl)imidazo[2,1- b]thiazole-3-acetic acid hydrazide. J. Fac. Pharm. Istanbul, 2015, 45, 127-138.
[http://dx.doi.org/10.16883/JFPIU.58800]
[http://dx.doi.org/10.16883/JFPIU.58800]
[74]
Andreani, A.; Rambaldi, M.; Locatelli, A. Synthesis and fungicide activity of 2,3-dihydroimidazo [2,1-b]thiazole-5-carboxamides. Pharm. Acta Helv., 1995, 70(4), 325-328.
[http://dx.doi.org/10.1016/0031-6865(95)00038-0] [PMID: 8765698]
[http://dx.doi.org/10.1016/0031-6865(95)00038-0] [PMID: 8765698]
[75]
Morigi, R.; Vitali, B.; Prata, C.; Palomino, R.A.N.; Graziadio, A.; Locatelli, A.; Rambaldi, M.; Leoni, A. Investigation on the effects of antimicrobial imidazo[2,1-b]thiazole derivatives on the genitourinary microflora. Med. Chem., 2018, 14(3), 311-319.
[http://dx.doi.org/10.2174/1573406413666171010110819] [PMID: 29032761]
[http://dx.doi.org/10.2174/1573406413666171010110819] [PMID: 29032761]
[76]
Shetty, N.S.; Koti, R.S.; Lamani, R.S.; Badiger, N.P.; Khazi, I.A.M. Synthesis and antimicrobial activities of some ethyl 2-arylthio-6- arylimidazo[2,1-b]thiazole-3- carboxylates and their sulfones. J. Sulfur Chem., 2008, 29, 539-547.
[http://dx.doi.org/10.1080/17415990802105747]
[http://dx.doi.org/10.1080/17415990802105747]
[77]
De Clercq, E.; Li, G. Approved antiviral drugs over the past 50 years. Clin. Microbiol. Rev., 2016, 29(3), 695-747.
[http://dx.doi.org/10.1128/CMR.00102-15] [PMID: 27281742]
[http://dx.doi.org/10.1128/CMR.00102-15] [PMID: 27281742]
[78]
Moussa, Z.; El-Sharief, M.A.M.S.; Abbas, S.Y. New imidazolidineiminothione derivatives: synthesis, spectral characterization and evaluation of antitumor, antiviral, antibacterial and antifungal activities. Eur. J. Med. Chem., 2016, 122, 419-428.
[http://dx.doi.org/10.1016/j.ejmech.2016.06.051] [PMID: 27393950]
[http://dx.doi.org/10.1016/j.ejmech.2016.06.051] [PMID: 27393950]
[79]
Barradas, J.S.; Errea, M.I.; D’Accorso, N.B.; Sepúlveda, C.S.; Damonte, E.B. Imidazo[2,1-b]thiazole carbohydrate derivatives: synthesis and antiviral activity against Junin virus, agent of Argentine hemorrhagic fever. Eur. J. Med. Chem., 2011, 46(1), 259-264.
[http://dx.doi.org/10.1016/j.ejmech.2010.11.012] [PMID: 21115214]
[http://dx.doi.org/10.1016/j.ejmech.2010.11.012] [PMID: 21115214]
[80]
Wang, N.Y.; Xu, Y.; Zuo, W.Q.; Xiao, K.J.; Liu, L.; Zeng, X.X.; You, X.Y.; Zhang, L.D.; Gao, C.; Liu, Z.H.; Ye, T.H.; Xia, Y.; Xiong, Y.; Song, X.J.; Lei, Q.; Peng, C.T.; Tang, H.; Yang, S.Y.; Wei, Y.Q.; Yu, L.T. Discovery of imidazo[2,1-b]thiazole HCV NS4B inhibitors exhibiting synergistic effect with other direct-acting antiviral agents. J. Med. Chem., 2015, 58(6), 2764-2778.
[http://dx.doi.org/10.1021/jm501934n] [PMID: 25710739]
[http://dx.doi.org/10.1021/jm501934n] [PMID: 25710739]
[81]
Güzeldemirci, U.N.; Karaman, B.; Küçükbasmaci, Ö. antibacterial, antitubercular and antiviral activity evaluations of some arylidenehydrazide derivatives bearing imidazo[2,1-b]thiazole moiety. Turk. J Pharm. Sci., 2017, 14(2), 157-163.
[http://dx.doi.org/10.4274/tjps.25743] [PMID: 32454607]
[http://dx.doi.org/10.4274/tjps.25743] [PMID: 32454607]
[82]
Güzeldemirci, N.U.; Pehlivan, E.; Naesens, L. Synthesis and antiviral activity evaluation of new 4-thiazolidinones bearing an imidazo[2,1-b]thiazole moiety. Marmara Pharm. J., 2018, 22, 237-248.
[http://dx.doi.org/10.12991/mpj.2018.61]
[http://dx.doi.org/10.12991/mpj.2018.61]
[83]
World Health Organization WHO Global Tuberculosis Report, 2015. Available at:
http://apps.who.int/iris/bitstream/10665/191102/1/9789241565059_eng.pdf
[84]
Raviglione, M.; Marais, B.; Floyd, K.; Lönnroth, K.; Getahun, H.; Migliori, G.B.; Harries, A.D.; Nunn, P.; Lienhardt, C.; Graham, S.; Chakaya, J.; Weyer, K.; Cole, S.; Kaufmann, S.H.E.; Zumla, A. Scaling up interventions to achieve global tuberculosis control: progress and new developments. Lancet, 2012, 379(9829), 1902-1913.
[http://dx.doi.org/10.1016/S0140-6736(12)60727-2] [PMID: 22608339]
[http://dx.doi.org/10.1016/S0140-6736(12)60727-2] [PMID: 22608339]
[85]
Brossier, F.; Boudinet, M.; Jarlier, V.; Petrella, S.; Sougakoff, W. Comparative study of enzymatic activities of new KatG mutants from low- and high-level isoniazid-resistant clinical isolates of Mycobacterium tuberculosis. Tuberculosis (Edinb.), 2016, 100, 15-24.
[http://dx.doi.org/10.1016/j.tube.2016.06.002] [PMID: 27553406]
[http://dx.doi.org/10.1016/j.tube.2016.06.002] [PMID: 27553406]
[86]
Moraski, G.C.; Seeger, N.; Miller, P.A.; Oliver, A.G.; Boshoff, H.I.; Cho, S.; Mulugeta, S.; Anderson, J.R.; Franzblau, S.G.; Miller, M.J. Arrival of Imidazo[2,1-b]thiazole-5-carboxamides: potent anti-tuberculosis agents that target QcrB. ACS Infect. Dis., 2016, 2(6), 393-398.
[http://dx.doi.org/10.1021/acsinfecdis.5b00154] [PMID: 27627627]
[http://dx.doi.org/10.1021/acsinfecdis.5b00154] [PMID: 27627627]
[87]
Samala, G.; Devi, P.B.; Saxena, S.; Meda, N.; Yogeeswari, P.; Sriram, D. Design, synthesis and biological evaluation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole derivatives as Mycobacterium tuberculosis pantothenate synthetase inhibitors. Bioorg. Med. Chem., 2016, 24(6), 1298-1307.
[http://dx.doi.org/10.1016/j.bmc.2016.01.059] [PMID: 26867485]
[http://dx.doi.org/10.1016/j.bmc.2016.01.059] [PMID: 26867485]
[88]
Andreani, A.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M. Synthesis and antitubercular activity of imidazo[2,1-b]thiazoles. Eur. J. Med. Chem., 2001, 36(9), 743-746.
[http://dx.doi.org/10.1016/S0223-5234(01)01266-1] [PMID: 11672884]
[http://dx.doi.org/10.1016/S0223-5234(01)01266-1] [PMID: 11672884]
[89]
Masferrer, J.L.; Zweifel, B.S.; Manning, P.T.; Hauser, S.D.; Leahy, K.M.; Smith, W.G.; Isakson, P.C.; Seibert, K. Selective inhibition of inducible cyclooxygenase 2 in vivo is antiinflammatory and nonulcerogenic. Proc. Natl. Acad. Sci. USA, 1994, 91(8), 3228-3232.
[http://dx.doi.org/10.1073/pnas.91.8.3228] [PMID: 8159730]
[http://dx.doi.org/10.1073/pnas.91.8.3228] [PMID: 8159730]
[90]
Banerjee, A.G.; Das, N.; Shengule, S.A.; Srivastava, R.S.; Shrivastava, S.K. Synthesis, characterization, evaluation and molecular dynamics studies of 5, 6-diphenyl-1,2,4-triazin-3(2H)-one derivatives bearing 5-substituted 1,3,4-oxadiazole as potential anti-inflammatory and analgesic agents. Eur. J. Med. Chem., 2015, 101, 81-95.
[http://dx.doi.org/10.1016/j.ejmech.2015.06.020] [PMID: 26117820]
[http://dx.doi.org/10.1016/j.ejmech.2015.06.020] [PMID: 26117820]
[91]
Palagiano, F.; Arenare, L.; Luraschil, E.; de Caprariis, P.; Abignente, E.; D’Amico, W.; Filippelli, M.; Rossi, F. Research on heterocyclic compounds. XXXIV. Synthesis and SAR study of some imidazo[2,1-b]thiazole carboxylic and acetic acids with antiinflammatory and analgesic activities. Eur. J. Med. Chem., 1995, 30, 901-909.
[http://dx.doi.org/10.1016/0223-5234(96)88309-7]
[http://dx.doi.org/10.1016/0223-5234(96)88309-7]
[92]
Tehrani, M.B.; Emami, S.; Asadi, M.; Saeedi, M.; Mirzahekmati, M.; Ebrahimi, S.M.; Mahdavi, M.; Nadri, H.; Moradi, A.; Moghadam, F.H.; Farzipour, S.; Vosooghi, M.; Foroumadi, A.; Shafiee, A. Imidazo[2,1-b]thiazole derivatives as new inhibitors of 15-lipoxygenase. Eur. J. Med. Chem., 2014, 87, 759-764.
[http://dx.doi.org/10.1016/j.ejmech.2014.10.011] [PMID: 25310714]
[http://dx.doi.org/10.1016/j.ejmech.2014.10.011] [PMID: 25310714]
[93]
Schmidt, T.J.; Rzeppa, S.; Kaiser, M.; Brun, R. Larrea tridentata-absolute configuration of its epoxylignans and investigations on its antiprotozoal activity. Phytochem. Lett., 2012, 5, 632-638.
[http://dx.doi.org/10.1016/j.phytol.2012.06.011]
[http://dx.doi.org/10.1016/j.phytol.2012.06.011]
[94]
Scribner, A.; Meitz, S.; Fisher, M.; Wyvratt, M.; Leavitt, P.; Liberator, P.; Gurnett, A.; Brown, C.; Mathew, J.; Thompson, D.; Schmatz, D.; Biftu, T. Synthesis and biological activity of anticoccidial agents: 5,6-diarylimidazo [2,1-b][1,3]thiazoles. Bioorg. Med. Chem. Lett., 2008, 18(19), 5263-5267.
[http://dx.doi.org/10.1016/j.bmcl.2008.08.063] [PMID: 18789686]
[http://dx.doi.org/10.1016/j.bmcl.2008.08.063] [PMID: 18789686]
[95]
Raeymaekers, A.H.; Allewijn, F.T.; Vandenberk, J.; Demoen, P.J.; Van Offenwert, T.T.; Janssen, P.A. Novel broad-spectrum anthelmintics. Tetramisole and related derivatives of 6-arylimidazo[2,1-b]thiazole. J. Med. Chem., 1966, 9(4), 545-551.
[http://dx.doi.org/10.1021/jm00322a023] [PMID: 5968020]
[http://dx.doi.org/10.1021/jm00322a023] [PMID: 5968020]
[96]
World Health Organization. Global Status Report on Non- Communicable Diseases 2014, Geneva, 2014. Available at:
https://www.who.int/nmh/publications/ncd-status-report-2014/en/
[97]
Leira, R.; Dávalos, A.; Silva, Y.; Gil-Peralta, A.; Tejada, J.; Garcia, M.; Castillo, J. Stroke Project, Cerebrovascular Diseases Group of the Spanish Neurological Society. Early neurologic deterioration in intracerebral hemorrhage: predictors and associated factors. Neurology, 2004, 63(3), 461-467.
[http://dx.doi.org/10.1212/01.WNL.0000133204.81153.AC] [PMID: 15304576]
[http://dx.doi.org/10.1212/01.WNL.0000133204.81153.AC] [PMID: 15304576]
[98]
Fischer, U.; Cooney, M.T.; Bull, L.M.; Silver, L.E.; Chalmers, J.; Anderson, C.S.; Mehta, Z.; Rothwell, P.M. Acute post-stroke blood pressure relative to premorbid levels in intracerebral haemorrhage versus major ischaemic stroke: a population-based study. Lancet Neurol., 2014, 13(4), 374-384.
[http://dx.doi.org/10.1016/S1474-4422(14)70031-6] [PMID: 24582530]
[http://dx.doi.org/10.1016/S1474-4422(14)70031-6] [PMID: 24582530]
[99]
Budriesi, R.; Ioan, P.; Locatelli, A.; Cosconati, S.; Leoni, A.; Ugenti, M.P.; Andreani, A.; Di Toro, R.; Bedini, A.; Spampinato, S.; Marinelli, L.; Novellino, E.; Chiarini, A. Imidazo[2,1-b]thiazole system: a scaffold endowing dihydropyridines with selective cardiodepressant activity. J. Med. Chem., 2008, 51(6), 1592-1600.
[http://dx.doi.org/10.1021/jm070681+] [PMID: 18303827]
[http://dx.doi.org/10.1021/jm070681+] [PMID: 18303827]
[100]
Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Bossa, R.; Chiericozzi, M.; Galatulas, I.; Salvatore, G. Synthesis and cardiotonic activity of imidazo [2, l-b] thiazoles bearing a lactam ring. Eur. J. Med. Chem., 1996, 31, 383-387.
[http://dx.doi.org/10.1016/0223-5234(96)89164-1]
[http://dx.doi.org/10.1016/0223-5234(96)89164-1]
[101]
Budriesi, R.; Ioan, P.; Leoni, A.; Pedemonte, N.; Locatelli, A.; Micucci, M.; Chiarini, A.; Galietta, L.J. Cystic fibrosis: a new target for 4-Imidazo[2,1-b]thiazole-1,4-dihydropyridines. J. Med. Chem., 2011, 54(11), 3885-3894.
[http://dx.doi.org/10.1021/jm200199r] [PMID: 21568323]
[http://dx.doi.org/10.1021/jm200199r] [PMID: 21568323]
[102]
Locatelli, A.; Cosconati, S.; Micucci, M.; Leoni, A.; Marinelli, L.; Bedini, A.; Ioan, P.; Spampinato, S.M.N.; 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(10), 3866-3877.
[http://dx.doi.org/10.1021/jm301839q] [PMID: 23586669]
[http://dx.doi.org/10.1021/jm301839q] [PMID: 23586669]
[103]
Woolley, M.L.; Marsden, C.A.; Fone, K.C. 5-ht6 receptors. Curr. Drug Targets CNS Neurol. Disord., 2004, 3(1), 59-79.
[http://dx.doi.org/10.2174/1568007043482561] [PMID: 14965245]
[http://dx.doi.org/10.2174/1568007043482561] [PMID: 14965245]
[104]
Cole, D.C.; Stock, J.R.; Lennox, W.J.; Bernotas, R.C.; Ellingboe, J.W.; Boikess, S.; Coupet, J.; Smith, D.L.; Leung, L.; Zhang, G.M.; Feng, X.; Kelly, M.F.; Galante, R.; Huang, P.; Dawson, L.A.; Marquis, K.; Rosenzweig-Lipson, S.; Beyer, C.E.; Schechter, L.E. Discovery of N1-(6-chloroimidazo[2,1-b][1,3]thiazole-5-sulfonyl)tryptamine as a potent, selective, and orally active 5-HT(6) receptor agonist. J. Med. Chem., 2007, 50(23), 5535-5538.
[http://dx.doi.org/10.1021/jm070521y] [PMID: 17948978]
[http://dx.doi.org/10.1021/jm070521y] [PMID: 17948978]
[105]
Beheshti, I.; Demirel, H. Alzheimer’s disease neuroimaging initiative. Probability distribution function-based classification of structural MRI for the detection of Alzheimer’s disease. Comput. Biol. Med., 2015, 64, 208-216.
[http://dx.doi.org/10.1016/j.compbiomed.2015.07.006] [PMID: 26226415]
[http://dx.doi.org/10.1016/j.compbiomed.2015.07.006] [PMID: 26226415]
[106]
Alzheimer’s Disease International. World Alzheimer Report 2016. Available at:
http://www.worldalzreport2016. org/,2016
[107]
Jin, J.; Wang, Y.; Shi, D.; Wang, F.; Davis, R.S.; Jin, Q.; Fu, W.; Foley, J.J.; Webb, E.F.; Dehaas, C.J.; Berlanga, M.; Burman, M.; Sarau, H.M.; Morrow, D.M.; Rao, P.; Kallal, L.A.; Moore, M.L.; Rivero, R.A.; Palovich, M.; Salmon, M.; Belmonte, K.E.; Busch-Petersen, J. Discovery of novel and long acting muscarinic acetylcholine receptor antagonists. J. Med. Chem., 2008, 51(16), 4866-4869.
[http://dx.doi.org/10.1021/jm800634k] [PMID: 18680280]
[http://dx.doi.org/10.1021/jm800634k] [PMID: 18680280]
[108]
Andreani, A.; Burnelli, S.; Granaiola, M.; Guardigli, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Rizzoli, M.; Varoli, L.; Roda, A. Chemiluminescent high-throughput microassay applied to imidazo[2,1-b]thiazole derivatives as potential acetylcholinesterase and butyrylcholinesterase inhibitors. Eur. J. Med. Chem., 2008, 43(3), 657-661.
[http://dx.doi.org/10.1016/j.ejmech.2007.04.018] [PMID: 17624631]
[http://dx.doi.org/10.1016/j.ejmech.2007.04.018] [PMID: 17624631]
[109]
Godin-Ethier, J.; Hanafi, L.A.; Piccirillo, C.A.; Lapointe, R. Indoleamine 2,3-dioxygenase expression in human cancers: clinical and immunologic perspectives. Clin. Cancer Res., 2011, 17(22), 6985-6991.
[http://dx.doi.org/10.1158/1078-0432.CCR-11-1331] [PMID: 22068654]
[http://dx.doi.org/10.1158/1078-0432.CCR-11-1331] [PMID: 22068654]
[110]
Tojo, S.; Kohno, T.; Tanaka, T.; Kamioka, S.; Ota, Y.; Ishii, T.; Kamimoto, K.; Asano, S.; Isobe, Y. Crystal structures and structure-activity relationships of imidazothiazole derivatives as IDO1 inhibitors. ACS Med. Chem. Lett., 2014, 5(10), 1119-1123.
[http://dx.doi.org/10.1021/ml500247w] [PMID: 25313323]
[http://dx.doi.org/10.1021/ml500247w] [PMID: 25313323]
[111]
Di Domenico, F.; Foppoli, C.; Coccia, R.; Perluigi, M. Antioxidants in cervical cancer: chemopreventive and chemotherapeutic effects of polyphenols. Biochim. Biophys. Acta, 2012, 1822(5), 737-747.
[http://dx.doi.org/10.1016/j.bbadis.2011.10.005] [PMID: 22019724]
[http://dx.doi.org/10.1016/j.bbadis.2011.10.005] [PMID: 22019724]
[112]
Abdel-Wahab, B.F.; Awad, G.E.A.; Badria, F.A. Synthesis, antimicrobial, antioxidant, anti-hemolytic and cytotoxic evaluation of new imidazole-based heterocycles. Eur. J. Med. Chem., 2011, 46(5), 1505-1511.
[http://dx.doi.org/10.1016/j.ejmech.2011.01.062] [PMID: 21353349]
[http://dx.doi.org/10.1016/j.ejmech.2011.01.062] [PMID: 21353349]
[113]
De, S.; Adhikari, S.; Tilak-Jain, J.; Menon, V.P.; Devasagayam, T.P. Antioxidant activity of an aminothiazole compound: possible mechanisms. Chem. Biol. Interact., 2008, 173(3), 215-223.
[http://dx.doi.org/10.1016/j.cbi.2008.03.011] [PMID: 18466888]
[http://dx.doi.org/10.1016/j.cbi.2008.03.011] [PMID: 18466888]
[114]
Cuendet, M.; Oteham, C.P.; Moon, R.C.; Pezzuto, J.M. Quinone reductase induction as a biomarker for cancer chemoprevention. J. Nat. Prod., 2006, 69(3), 460-463.
[http://dx.doi.org/10.1021/np050362q] [PMID: 16562858]
[http://dx.doi.org/10.1021/np050362q] [PMID: 16562858]
[115]
Metaye, T.; Millet, C.; Kraimps, J.L.; Saunier, B.; Barbier, J.; Begon, F. Effect of bromolevamisole and other imidazo [2,1-b] thiazole derivatives on adenylate cyclase activity. Biochem. Pharmacol., 1992, 43(7), 1507-1511.
[http://dx.doi.org/10.1016/0006-2952(92)90208-Z] [PMID: 1314603]
[http://dx.doi.org/10.1016/0006-2952(92)90208-Z] [PMID: 1314603]
[116]
Harraga, S.; Nicod, L.; Drouhin, J.P.; Xicluna, A.; Panouse, J.J.; Seilles, E.; Robert, J.F. Imidazo[2,1-b]thiazole derivatives. XI. Modulation of the CD,-receptor of human T trypsinized lymphocytes by several imidazo[2,1-b]thiazoles. Eur. J. Med. Chem., 1994, 29, 309-315.
[http://dx.doi.org/10.1016/0223-5234(94)90101-5]
[http://dx.doi.org/10.1016/0223-5234(94)90101-5]
[117]
Mona, C.E.; Besserer-Offroy, É.; Cabana, J.; Leduc, R.; Lavigne, P.; Heveker, N.; Marsault, É.; Escher, E. Design, synthesis, and biological evaluation of CXCR4 ligands. Org. Biomol. Chem., 2016, 14(43), 10298-10311.
[http://dx.doi.org/10.1039/C6OB01484D] [PMID: 27752700]
[http://dx.doi.org/10.1039/C6OB01484D] [PMID: 27752700]
[118]
Andreani, A.; Rambaldi, M.; Mascellani, G.; Rugarli, P. Synthesis and diuretic activity of imidazo[2,1-b]thiazole acetohydrazones. Eur. J. Med. Chem., 1987, 22, 19-22.
[http://dx.doi.org/10.1016/0223-5234(87)90169-3]
[http://dx.doi.org/10.1016/0223-5234(87)90169-3]
[119]
Andreani, A.; Rambaldi, M.; Locatelli, A.; Isetta, A.M. Synthesis and mitogenic activity of new imidazo[2,1- b]thiazoles. Eur. J. Med. Chem. 1991, 26, 335-337.
[http://dx.doi.org/10.1016/0223-5234(91)90067-W]
[http://dx.doi.org/10.1016/0223-5234(91)90067-W]