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Microwave promoted synthesis and anticological screening of β-aminobisphosphonates-based benzothiazole motif against human breast and colon cancer diseases

Wafaa M. Abdou, Maha D. Khidre, and Abeer A. Shaddy

National Research Centre, Dokki, Egypt

 

E-mail: wabdou@link.net

Abstract: New antineoplastic series of substituted benzothiazolo-β-aminobisphosphonic acids have been developed on the basis of the prospecting potency of the benzothiazole motifs and the aminomethylenebisphosphonate moiety as well as on the prediction of the biological activity utilizing computer program PASS, version 2014-1. Target compounds were obtained in excellent yields (70–90%) via Phospha–Michael-type addition reaction of tetraethyl methylene-1,1-bisphosphonate reagent to a group of Schiff bases incorporating benzothiazole moiety. The reactions proceeded under microwave irradiation, utilizing the advantages of the environment, friendly protocol such as high efficiency, short reaction time, and excellent yields. In consistency with the prospected results, the new NBP acids revealed positive properties against human breast and colon tumor cell lines. Remarkable potency for six lead compounds (out of 12) was observed against breast (MCF7, MDAMB/435, MDAMB/231/ATCC, HS-578T with GI50: 2.05–6.47 μM) and colon (COLO-205, HCT-116, HCC-2998, and SW-620 with GI50: 3.03–7.92 μM) carcinoma cell lines when compared with the positive control Adriamycin (breast, GI50: 3.27–6.64 μM; colon, GI50: 4.09–8.75 μM). Notably, there is a consistency between the prediction and the determined biological results.

Keywords: β-Aminobisphosphonates ; Benzothiazoles ; Antitumor agents ; Phospha–Michael addition ; Structure activity relationships 

Full paper is available at www.springerlink.com.

DOI: 10.1007/s11696-018-0505-8

 

Chemical Papers 72 (11) 2753–2768 (2018)

Wednesday, June 16, 2021

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