Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran–imidazolium salt derivatives

Zhang, Chaobo; Liu, Yang; Liu, Zhengfen; Duan, Shengzu; Li, Minyan; Chen, Wen; Li, Yan; Zhang, Hongbin; Yang, Xiaodong

doi:10.1016/j.bmcl.2017.02.053

Cited by 20 publications

(13 citation statements)

References 37 publications

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“…25−29 Many compounds showed potential antitumor activity, such as NTIB. 25 Studies on molecular targets and docking calculations suggested that these imidazolium salt hybrids may be mammalian target of rapamycin (mTOR) signaling inhibitors. 25−27…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Anticancer Activity of Novel Trimethoxyphenyl-Derived Chalcone-Benzimidazolium Salts

Yang

et al. 2019

ACS Omega

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A series of novel trimethoxyphenyl-derived chalcone-benzimidazolium salts were synthesized. The biological properties of the compounds were screened in vitro against five different human tumor cell lines. The results suggest that the 5,6-dimethyl-benzimidazole or 2-methyl-benzimidazole ring as well as the 2-naphthylmethyl, 4-methylbenzyl, or 2-naphthylacyl substituent at position-3 of the benzimidazole ring was important to the cytotoxic activity. Notably, (E)-5,6-dimethyl-3-(naphthalen-2-ylmethyl)-1-(3-(4-(3-(3,4,5-trimethoxyphenyl)acryloyl)phenoxy)propyl)-1H-benzo[d]imidazol-3-ium bromide (7f) was more selective to HL-60, MCF-7, and SW-480 cell lines with IC50 values 8.0-, 11.1-, and 5.8-fold lower than DDP. Studies of the antitumor mechanism of action showed that compound 7f could induce cell-cycle G1 phase arrest and apoptosis in SMMC-7721 cells.

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Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Anticancer Activity of Novel Trimethoxyphenyl-Derived Chalcone-Benzimidazolium Salts

Yang

et al. 2019

ACS Omega

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“…Several reports have shown that imidazolium salts possess promising anticancer activities [13,16,[32][33][34][35][36][37][38][39][40][41]. We evaluated the anticancer activities of lithocholic acid-based imidazolium salts (S1-S10) against three different colorectal cancer cell lines (DLD-1, HT-29, and Caco-2).…”

Section: Imidazolium Salts Decrease Colon Cancer Viability and Metabo...mentioning

confidence: 99%

“…Further research with dibenzo [b,d]furane-imidazole hybrid compounds exhibited cytotoxic activity selectively against lung carcinoma (A549) and myeloid liver carcinoma (SMMC-7721) with the G1 phase cell cycle arrest and apoptosis [13]. A series of novel 4-substituted 2,3,6,7-tetrahydrobenzo [1,2-b;4,5-b ]difuran-1H-imidazolium salts also exhibited cytotoxic effect against A549 and SW480 cell lines [38]. De Bord et al [37] showed high anticancer activity of alkyl-and N,N -bisnaphthyl-substituted imidazolium salts against lung cancer cell lines (NCI-H460, NCI-H1975, HCC827, A549).…”

Section: Imidazolium Salts Decrease Colon Cancer Viability and Metabo...mentioning

confidence: 99%

Establishment of In Vitro and In Vivo Anticolorectal Cancer Efficacy of Lithocholic Acid-Based Imidazolium Salts

Sawicka

Hryniewicka

Gohal

et al. 2022

IJMS

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Imidazolium salts (IMSs) are the subject of many studies showing their anticancer activities. In this research, a series of novel imidazolium salts substituted with lithocholic acid (LCA) and alkyl chains of various lengths (S1–S10) were evaluated against colon cancer cells. A significant reduction in the viability and metabolic activity was obtained in vitro for DLD-1 and HT-29 cell lines when treated with tested salts. The results showed that the activities of tested agents are directly related to the alkyl chain length, where S6–S8 compounds were the most cytotoxic against the DLD-1 line and S4–S10 against HT-29. The research performed on the xenograft model of mice demonstrated a lower tendency of tumor growth in the group receiving compound S6, compared with the group receiving 5-fluorouracil (5-FU). Obtained results indicate the activity of S6 in the induction of apoptosis and necrosis in induced colorectal cancer. LCA-based imidazolium salts may be candidates for chemotherapeutic agents against colorectal cancer.

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“…Compound 13 showed selectivity for A549, SMMC-7721, and SW-480 cancer cell lines. Some derivatives of this series also exhibited the phenomenon of apoptosis and seized cell cycle in the G1 stage [36]. Zhou et al manufactured hexahydropyrrolo [2,3b]indole-1H-imidazolium salts as anticancer agents.…”

Section: Hybrid Molecules Containing Benzimidazolium Saltsmentioning

confidence: 99%

The Anticancer Profile of Benzimidazolium Salts and Their Metal Complexes

Khan¹,

Mohsin²,

Aslam³

et al. 2022

Benzimidazole

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Cancer is the most lethal ailment throughout the world in the present era. The development of new anticancer remedies with minor unhealthful effects and an alternate mechanism is crucial. Benzimidazole is a distinguished heterocyclic compound and is now recognized as the privileged scaffold for new drug discovery. This chapter deals with the anticancer capability of benzimidazolium salts and their metal complexes. The benzimidazolium derivatives have been prepared by the introduction of aliphatic and aromatic groups at two nitrogen atoms of the benzimidazole ring. Other modifications include hybridization with other pharmacophores and the preparation of metal complexes. The potent derivatives presented in this review can serve as novel drug candidates against cancer.

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Synthesis and cytotoxic activity of novel tetrahydrobenzodifuran–imidazolium salt derivatives

Cited by 20 publications

References 37 publications

Design, Synthesis, and Anticancer Activity of Novel Trimethoxyphenyl-Derived Chalcone-Benzimidazolium Salts

Design, Synthesis, and Anticancer Activity of Novel Trimethoxyphenyl-Derived Chalcone-Benzimidazolium Salts

Establishment of In Vitro and In Vivo Anticolorectal Cancer Efficacy of Lithocholic Acid-Based Imidazolium Salts

The Anticancer Profile of Benzimidazolium Salts and Their Metal Complexes

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