Synthesis, Characterization and Antitumor Activity of Benzimidazole Phosphonate Derivatives | ||
| Egyptian Journal of Chemistry | ||
| Volume 67, Issue 13, December 2024, Pages 443-452 PDF (606.86 K) | ||
| Document Type: Original Article | ||
| DOI: 10.21608/ejchem.2024.257129.9050 | ||
| Authors | ||
| Eman Sabry1; Sherifa M. Abu Bakr2; Maha D. Khidre1; Hanem M. Awad3; Ashraf A. Sediek* 1 | ||
| 1Chemical Industries Research Institute, National Research Centre, Elbehouth St, Dokki, Cairo 12622, Egypt | ||
| 2Department of Chemistry of Natural and Microbial Products, Institute of Pharmaceutical and Drug Industries, National Research Centre, Dokki, Cairo, Egypt | ||
| 3Department of Tanning Materials and Leather Technology, National Research Centre, 33 El-Bohouth St. (former El Tahrir St.), P.O. 12622, Dokki, Giza, Egypt. | ||
| Abstract | ||
| A series of Benzimidazole derivatives were obtained via reaction of 2-chloro-1H-benzo[d]imidazole (1) with morpholine, which produce benzo[d]imidazol-yl-morpholine 2 that react with chloroacetonitrile to give (benzo[d]imidazol-yl)acetonitrile 3, by its next reaction with hydrazine hydrate afforded the key intermediate 4, that afford thiadiazole derivatives 5 by its reaction with carbon disulfide via cyclization reaction. Alkylation of compound 5 with ethyl bromoacetate, afforded benzo[d]imidazolo derivative 6, that react with thioglycolic acid to give thiazolidine compound in suitable conditions. Also Benzimidazole 1 reacted with various Wittig Horner reagents in DMF to afford phosphoryl and phosphonates derivatives 12a-e in moderate yields. On the other hand, 1 react with trialkyl phosphites to yield the known phosphonates derivatives 14a-c in high yields, also we obtained the same products by reacting 1 with dialkyl phosphites. In addition, hexaalkyltriamidophosphites were applied to 1 in ethanol to afford phosphonic diamide derivatives 17a-c in high yields through addition-elimination reaction. Antitumor activity of the newly synthesized compounds were tested on three cell lines of breast (MCF7) and liver (HepG2) carcinoma cell lines and HCT-116 cancer cells together with human healthy cell line (BJ-1) using the MTT assay. Most compounds suppressed three cancer cells (HCT-116, HepG2 and MCF-7) and exhibited considerable anticancer properties in a dose-dependent manner | ||
| Keywords | ||
| Chloro-benzo[d]imidazole; anticancer; microwave-assisted; phosphorus Horner reagents; Heterocyclic compounds | ||
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