Synthesis of 2-aminobenzothiazole hybrids containing 2-aminobenzamide group via amide bridge
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https://doi.org/10.54939/1859-1043.j.mst.81.2022.79-85Keywords:
2-aminobenzothiazole; 2-aminobenzamide; Synthesis; Cytotoxicity; Hybrids.Abstract
The hybrid compound of 2-aminobenzothiazole containing 2-aminobenzamide group via amide bridge was designed and successfully synthesized, and the structure was determined by the methods of Nuclear Magnetic Resonance (NMR), High resolution - mass spectra (HRMS). The synthesized compound was also evaluated for its anticancer activity in vitro on two cell lines A549 and SW480. The obtained results showed that compound (3) showed no activity against SW480 cell line but showed toxicity against A549 cell line with IC50 value of 29.49 µM.
References
[1]. World Health Organization (WHO). "Cancer". https://www.who.int/health-topics/cancer#tab=tab_1. (2021).
[2]. Ferlay J, E.M., Lam F, Colombet M, Mery L, Piñeros M, "Global Cancer Observatory: Cancer Today. Lyon: International Agency for Research on Cancer"; https://gco.iarc.fr/today, (2020)
[3]. Sung, H., et al., "Global Cancer Statistics 2020: GLOBOCAN Estimates of Incidence and Mortality Worldwide for 36 Cancers in 185 Countries". CA Cancer J Clin, 71(3), pp. 209-249, (2021). DOI: https://doi.org/10.3322/caac.21660
[4]. Victor Facchinetti, R.d.R.R., Claudia R.B. Gomes and Thatyana R.A. Vasconcelos, "Chemistry and Biological Activities of 1,3-Benzothiazoles". Mini-Reviews in Organic Chemistry, 9, pp. 44-53, (2012). DOI: https://doi.org/10.2174/157019312799079929
[5]. Kok, S.H., et al., "Synthesis and anti-cancer activity of benzothiazole containing phthalimide on human carcinoma cell lines". Bioorg Med Chem, 16(7), pp. 3626-31, (2008). DOI: https://doi.org/10.1016/j.bmc.2008.02.005
[6]. Mohamed, L.W., et al., "Synthesis and cytotoxic activity of certain benzothiazole derivatives against human MCF-7 cancer cell line". Chem Biol Drug Des, 89(4), pp. 566-576, (2017). DOI: https://doi.org/10.1111/cbdd.12879
[7]. Heo, Y., et al., "A highly regioselective synthesis of 2-aryl-6-chlorobenzothiazoles employing microwave-promoted Suzuki–Miyaura coupling reaction". Tetrahedron Letters, 47(18), pp. 3091-3094, (2006). DOI: https://doi.org/10.1016/j.tetlet.2006.02.152
[8]. R J Alaimo, S.S.P., R Freedman, "Synthesis and antibacterial evaluation of 2-(Substituted Phenylureido)-4-thiocyanatobenzothiazoles". Journal of Pharmaceutical Sciences, 67(2), pp. 281–282, (1978). DOI: https://doi.org/10.1002/jps.2600670247
[9]. Singh, M., et al., "Design, synthesis and mode of action of some benzothiazole derivatives bearing an amide moiety as antibacterial agents". RSC Adv., 4(36), pp. 19013-19023, (2014). DOI: https://doi.org/10.1039/C4RA02649G
[10]. Deniz Songül Dogruer, S.Ü., Mustafa Fethi Sahin, Erdem Yegilada, "Anti-nociceptive and anti-inflammatory activity of some (2-benzoxazolone-3-yl and 2-benzothiazolone-3-yl) acetic acid derivatives". IL Farmaco, 53(1), pp. 80-84, (1998). DOI: https://doi.org/10.1016/S0014-827X(97)00017-7
[11]. Vicini, P., et al., "Synthesis and biological evaluation of benzo[d]isothiazole, benzothiazole and thiazole Schiff bases". Bioorganic & Medicinal Chemistry, 11(22), pp. 4785-4789, (2003). DOI: https://doi.org/10.1016/S0968-0896(03)00493-0
[12]. Xie, R., et al., "Design, synthesis and biological evaluation of novel 2-aminobenzamides containing dithiocarbamate moiety as histone deacetylase inhibitors and potent antitumor agents". Eur J Med Chem, 143, pp. 320-333, (2018). DOI: https://doi.org/10.1016/j.ejmech.2017.08.041
[13]. Ryan, Q.C., et al., "Phase I and pharmacokinetic study of MS-275, a histone deacetylase inhibitor, in patients with advanced and refractory solid tumors or lymphoma". J Clin Oncol, 23(17), pp. 3912-22, (2005). DOI: https://doi.org/10.1200/JCO.2005.02.188
[14]. Zhou N, M.O., Raeppel S, Leit S, Frechette S, Gaudette F, Paquin I, Bernstein N, Bouchain G, Vaisburg A, Jin Z, Gillespie J, Wang J, Fournel M, Yan PT, Trachy-Bourget MC, Kalita A, Lu A, Rahil J, MacLeod AR, Li Z, Besterman JM, Delorme D, "Discovery of N-(2-aminophenyl)- 4-[(4-pyridin-3-ylpyrimidin-2-ylamino)methyl]benzamide (MGCD0103), an orally active histone deacetylase inhibitor". Journal of Medicinal Chemistry, 51, pp. 4072-4075, (2008). DOI: https://doi.org/10.1021/jm800251w
[15]. Đào Thị Kim Oanh, Luận án tiến sĩ, "Tổng hợp và thử hoạt tính sinh học của một số dẫn chất acid hydroxamic hướng ức chế enzym histon deacetylase", trang 60, (2013).
[16]. Robert H. Shoemaker, D.A.S., Giovanni Melillo, Michael J. Currens, Anne P. Monks, Alfred A. Rabow, David G. Covell and Edward A. Sausville, "Application of high-throughput, molecular-targeted screening to anticancer drug discovery". Current topics in medicinal chemistry , 2(3), 229-246, (2002). DOI: https://doi.org/10.2174/1568026023394317
[17]. Hughes, J.P., et al., "Principles of early drug discovery". Br J Pharmacol, 162(6), pp. 1239-49, (2011). DOI: https://doi.org/10.1111/j.1476-5381.2010.01127.x
[18]. Michael C. Alley, D.A.S., Anne Monks, Miriam L. Hursey, Maciej J. Czerwinski, Donald L. Fine, Betty J. Abbott, Joseph G. Mayo, Robert H. Shoemaker, and Michael R. Boyd, "Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay". Cancer research. 48(3), pp. 589-601, (1988).
[19]. Philip Skehan, R.S., Dominic Scudiero, Anne Monks, James, D.V. McMahon, Jonathan T. Warren, Heidi Bokesch, Susan, and M.R.B. Kenney, "New colorimetric cytotoxic assay for anticancer-drug screening". Journal of the National Cancer Institute, 82(13), pp. 1107-1112, (1990). DOI: https://doi.org/10.1093/jnci/82.13.1107
[20]. Dang Thi Tuyet Anh, D.T.C., Le Nhat Thuy Giang, Nguyen Thi Hien, Vu Ngoc Doan, Nguyen Ha Thanh, Nguyen Van Tuyen, Phan Van Kiem, "Design, Synthesis and Cytotoxic Evaluation of Novel Lupane Triterpenoid and Ursolic Acid Derived 2-Aminobenzamides". Natural Product Communications, 13(7), pp. 817-822, (2018). DOI: https://doi.org/10.1177/1934578X1801300708
