Abstract
In this work, 2-(4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio)-N-(thiazol-2-yl) acetamide derivatives were synthesized by reacting 4,5-dimethyl-1-(phenylamino)-1H-imidazole-2(3H)-thione derivatives with some 2-chloro-N-(thiazol-2-yl)acetamide compounds. The structure of synthesized compounds was confirmed by IR, 1H NMR, and mass spectra. Anticancer activities of the compounds selected by the National Cancer Institute were investigated by testing against a panel of 60 different human tumor cell lines derived from nine neoplastic cancer types. Compounds 7, 13, and 23 exhibited reasonable anticancer activity against the screened cancer types with relatively low GI50 values. The compounds showed high activity against melanoma-type cell lines.
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References
Adjei AA, Buolamwini JK (2006) Anticancer agents, strategies for discovery and clinical testing. Elsevier, New York
Amr AEGE, Sabrry NM, Abdalla MM, Abdel-Wahab BF (2009) Synthesis, antiarrhythmic and anticoagulant activities of novel thiazolo derivatives from methyl 2-(thiazol-2-ylcarbamoyl)acetate. Eur J Med Chem 44(2):725–735. doi:10.1016/j.ejmech.2008.05.004
Barone R, Chanon M, Gallo R (1979) Aminothiazole and their derivatives. Wiley, New York
Bellina F, Cauteruccio S, Rossi R (2007) Synthesis and biological activity of vicinal diaryl-substituted 1H-imidazoles. Tetrahedron 63(22):4571–4624. doi:10.1016/j.tet.2007.02.075
Bogdanović G, Kojić V, Srdić T, Jakimov D, Djuran MI, Bugarčić ŽD, Baltić M, Baltić VV (2002) Growth effects of some platinum(II) complexes with sulfur-containing carrier ligands on MCF7 human breast cancer cell line upon simultaneous administration with taxol. Met-Based Drugs 9(1–2):33–43
Bolos CA, Papazisis KT, Kortsaris AH, Voyatzi S, Zambouli D, Kyriakidis DA (2002) Antiproliferative activity of mixed-ligand dien-Cu(II) complexes with thiazole, thiazoline and imidazole derivatives. J Inorg Biochem 88(1):25–36
Bondock S, Fadaly W, Metwally MA (2010) Synthesis and antimicrobial activity of some new thiazole, thiophene and pyrazole derivatives containing benzothiazole moiety. Eur J Med Chem 45(9):3692–3701
Boyd MR (1989) Cancer: principles and practice of oncology 3. Lippincott, Philadelphia
Bujdakova H, Muckova M (1994) Antifungal activity of a new benzothiazole derivative against candida in-vitro and in-vivo. Int J Antimicrob Ag 4(4):303–308
Crane L, Anastassiadou M, El Hage S, Stigliani JL, Baziard-Mouysset G, Payard M, Leger JM, Bizot-Espiard JG, Ktorza A, Caignard DH, Renard P (2006) Design and synthesis of novel imidazoline derivatives with potent antihyperglycemic activity in a rat model of type 2 diabetes. Bioorg Med Chem 14(22):7419–7433
Demirayak S, Kayagil I, Yurttas L (2011) Microwave supported synthesis of some novel 1,3-diarylpyrazino[1,2-a] benzimidazole derivatives and investigation of their anticancer activities. Eur J Med Chem 46(1):411–416
Dulik DM, Fenselau C, Hilton J (1986) Characterization of melphalan-glutathione adducts whose formation is catalyzed by glutathione transferases. Biochem Pharmacol 35(19):3405–3409
El-Sharief AMS, Moussa Z (2009) Synthesis, characterization and derivatization of some novel types of mono- and bis-imidazolidineiminothiones and imidazolidineiminodithiones with antitumor, antiviral, antibacterial and antifungal activities—part I. Eur J Med Chem 44(11):4315–4334
Geronikaki A, Hadjipavlou-Litina D, Amourgianou M (2003) Novel thiazolyl, thiazolinyl and benzothiazolyl Schiff bases as possible lipoxygenase’s inhibitors and anti-inflammatory agents. Farmaco 58(7):489–495
Graczyk PP, Khan A, Bhatia GS, Palmer V, Medland D, Numata H, Oinuma H, Catchick J, Dunne A, Ellis M, Smales C, Whitfield J, Neame SJ, Shah B, Wilton D, Morgan L, Patel T, Chung R, Desmond H, Staddon JM, Sato N, Inoue A (2005) The neuroprotective action of JNK3 inhibitors based on the 6,7-dihydro-5H-pyrrolo[1,2-a]imidazole scaffold. Bioorg Med Chem Lett 15(21):4666–4670
Grever MR, Schepartz SA, Chabner BA (1992) The national-cancer-institute—cancer drug discovery and development program. Semin Oncol 19(6):622–638
Grover R, Dhein S (2001) Structure-activity relationships of novel peptides related to the antiarrhythmic peptide AAP10 which reduce the dispersion of epicardial action potential duration. Peptides 22(7):1011–1021
Koti RS, Kolavi GD, Hegde VS, Khazi IM (2007) Intramolecular amidation: synthesis of novel thiazole-fused diazepinones. Synth Commun 37(1–3):99–105
Krezel I (1998) New derivatives of imidazole as potential anticancer agents. Farmaco 53(5):342–345
Kumar D, Patel G, Chavers AK, Chang KH, Shah K (2011) Synthesis of novel 1,2,4-oxadiazoles and analogues as potential anticancer agents. Eur J Med Chem 46(7):3085–3092
Lagoja IM, Pannecouque C, Van Aerschot A, Witvrouw M, Debyser Z, Balzarini J, Herdewijn P, De Clercq E (2003) N-aminoimidazole derivatives inhibiting retroviral replication via a yet unidentified mode of action. J Med Chem 46(8):1546–1553
Luzina EL, Popov AV (2009) Synthesis and anticancer activity of N-bis(trifluoromethyl)alkyl-N′-thiazolyl and N-bis(trifluoromethyl)alkyl-N′-benzothiazolyl ureas. Eur J Med Chem 44(12):4944–4953
Milhaud D, Fagni L, Bockaert J, Lafon-Cazal M (2000) Imidazoline-induced neuroprotective effects result from blockade of NMDA receptor channels in neuronal cultures. Neuropharmacology 39(12):2244–2254
Monks A, Scudiero D, Skehan P, Shoemaker R, Paull K, Vistica D, Hose C, Langley J, Cronise P, Vaigrowolff A, Graygoodrich M, Campbell H, Mayo J, Boyd M (1991) Feasibility of a high-flux anticancer drug screen using a diverse panel of cultured human tumor-cell lines. J Natl Cancer I 83(11):757–766
National Cancer Institute (2012) http://dtp.nci.nih.gov Accessed 12 March 2012
Park JH, El-Gamal MI, Lee YS, Oh CH (2011) New imidazo[2,1-b]thiazole derivatives: synthesis, in vitro anticancer evaluation, and in silico studies. Eur J Med Chem 46(12):5769–5777
Rostom SAF, Ashour HMA, El Razik HAA, Abd El Fattah AEFH, El-Din NN (2009) Azole antimicrobial pharmacophore-based tetrazoles: synthesis and biological evaluation as potential antimicrobial and anticonvulsant agents. Bioorg Med Chem 17(6):2410–2422
Schantl JG, Lagoja IM (1997) Direct synthetic approach to N-substituted 1-amino-2,3-dihydro-1H-imidazole-2-thiones. Heterocycles 45(4):691–700
Siddiqui N, Ahsan W (2010) Triazole incorporated thiazoles as a new class of anticonvulsants: design, synthesis and in vivo screening. Eur J Med Chem 45(4):1536–1543
Singh N, Sharma US, Sutar N, Kumar S, Sharma UK (2010) Synthesis and antimicrobial activity of some novel 2-amino thiazole derivatives. J Chem Pharm Res 2(3):691–698
Tseng CH, Lin CS, Shih PK, Tsao LT, Wang JP, Cheng CM, Tzeng CC, Chen YL (2009) Furo[3′,2′:3,4]naphtho[1,2-d]imidazole derivatives as potential inhibitors of inflammatory factors in sepsis. Bioorg Med Chem 17(18):6773–6779
Zav’yalov SI, Kravchenko NE, Ezhova GI, Kulikova LB, Zavozin AG, Dorofeeva OV (2007) Synthesis of 2-aminothiazole derivatives. Pharm Chem J 41(2):105–108
Zhan P, Liu XY, Zhu JJ, Fang ZJ, Li ZY, Pannecouque C, De Clercq E (2009) Synthesis and biological evaluation of imidazole thioacetanilides as novel non-nucleoside HIV-1 reverse transcriptase inhibitors. Bioorg Med Chem 17(16):5775–5781
Acknowledgments
The authors would like to thank Eskişehir Osmangazi University for support and the National Cancer Institute (NCI), Bethesda, MD, USA, for in vitro screening of the compounds in human cancer cell lines.
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Duran, M., Demirayak, Ş. Synthesis of 2-[4,5-dimethyl-1-(phenylamino)-1H-imidazol-2-ylthio]-N-(thiazole-2-yl)acetamide derivatives and their anticancer activities. Med Chem Res 22, 4110–4124 (2013). https://doi.org/10.1007/s00044-012-0411-5
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DOI: https://doi.org/10.1007/s00044-012-0411-5