Synthesis and antitumor activity of aza-brazilan derivatives containing imidazolium salt pharmacophores

Huang, Mingqin; Duan, Shengzu; Ma, Xueqiong; Cai, Bicheng; Wu, Dongmei; Li, Yan; Li, Liang; Zhang, Hongbin; Yang, Xiaodong

doi:10.1039/c9md00112c

Cited by 9 publications

(5 citation statements)

References 42 publications

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“…The introduction of electron-withdrawing groups on the aza-brazilin nucleus produced more active derivatives. Derivatives having an alkyl chain as linker groups produce higher potency as compared to acyl chains [31]. Zhou et al also used a hybrid molecular strategy to conjugate N-substituted tetrahydro-β-carbolines with imidazolium salts.…”

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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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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“…In this context, our group has devoted to the synthesis of novel imidazolium salt derivatives and found a series of promising compounds with antitumor activity (Chen et al, 2013;Wang et al, 2013;Xu et al, 2014b;Xu et al, 2015;Zhou et al, 2016a;Zhou et al, 2016b). Further mechanistic studies confirmed that these imidazolium salt derivatives can induce cell cycle arrest and apoptosis in tumor cells (Liu et al, 2013;Liu et al, 2015;Huang et al, 2019). The representative examples are an effective antitumor active diosgenin-imidazolium salt and a new mTOR pathway inhibitor B591 (Figure 1) (Deng et al, 2019;Zhou et al, 2019).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles

et al. 2023

Self Cite

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Three series of podophyllotoxin derivatives with various nitrogen-containing heterocycles were designed and synthesized. The antitumor activity of these podophyllotoxin derivatives was evaluated in vitro against a panel of human tumor cell lines. The results showed that podophyllotoxin-imidazolium salts and podophyllotoxin-1,2,4-triazolium salts a1–a20 exhibited excellent cytotoxic activity. Among them, a6 was the most potent cytotoxic compound with IC50 values of 0.04–0.29 μM. Podophyllotoxin-1,2,3-triazole derivatives b1–b5 displayed medium cytotoxic activity, and podophyllotoxin-amine compounds c1–c3 has good cytotoxic activity with IC50 value of 0.04–0.58 μM. Furthermore, cell cycle and apoptosis experiments of compound a6 were carried out and the results exhibited that a6 could induce G2/M cell cycle arrest and apoptosis in HCT-116 cells.

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“…Previously, our research group has reported a series of works on the design, synthesis, and antitumor activity of imidazole salt compounds. [ 11–24 ] One of the most representative compounds is the imidazolium salt NIBI (Figure 1) which presents powerful in vitro and in vivo antitumor activity, and this study result is a hallmark of our group's breakthrough in this field. [ 25 ] We also studied the antitumor mechanism of some imidazolium salts derivatives, the results showed that they can induce cell cycle arrest and apoptosis of tumor cells.…”

Section: Introductionmentioning

confidence: 99%

“…[ 25 ] We also studied the antitumor mechanism of some imidazolium salts derivatives, the results showed that they can induce cell cycle arrest and apoptosis of tumor cells. [ 13–15 ]…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antitumor activity of novel hybrid compounds between 1,4‐benzodioxane and imidazolium salts

Liu

Zhang

Dong

et al. 2022

Archiv der Pharmazie

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A series of novel hybrid compounds between 1,4‐benzodioxane and imidazolium salts was designed and prepared. The compounds were evaluated in vitro against a panel of human tumor cell lines (K562, SMMC‐7721, and A‐549). The structure–activity relationship results demonstrated that the 2‐methyl‐benzimidazole or 5,6‐dimethyl‐benzimidazole ring and substitution of the imidazolyl‐3‐position with a 4‐phenylphenacyl substituent were critical for promoting cytotoxic activity. Particularly, compound 25 was found to be the most potent compound with IC50 values of 1.06–8.31 μM against the three human tumor cell lines and exhibited higher selectivity to K562 and SMMC‐7721 cells with IC50 values 4.5‐ and 4.7‐fold lower than cisplatin. Moreover, compound 25 inhibited cell proliferation by inducing the G0/G1 cell cycle arrest and apoptosis in SMMC‐7721 cells.

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Synthesis and antitumor activity of aza-brazilan derivatives containing imidazolium salt pharmacophores

Abstract: A series of novel aza-brazilan derivatives containing imidazolium salt pharmacophores were synthesized and their antitumor structure–activity relationship studies were reported.

Cited by 9 publications

References 42 publications

The Anticancer Profile of Benzimidazolium Salts and Their Metal Complexes

The Anticancer Profile of Benzimidazolium Salts and Their Metal Complexes

Synthesis and anticancer activity of podophyllotoxin derivatives with nitrogen-containing heterocycles

Synthesis and antitumor activity of novel hybrid compounds between 1,4‐benzodioxane and imidazolium salts

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