Design of novel bis-benzimidazole derivatives as DNA minor groove binding agents

Wang, Xiujun; Yang, Mingli; Zhang, Lanping; Tong, Yao; Chen, Cheng; Mao, Liangang; Wang, Yin; Wu, Jie

doi:10.1016/j.cclet.2014.01.019

Cited by 11 publications

(3 citation statements)

References 14 publications

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“…ODAA was synthesized by acetylation of 4,4 ′ -oxydianiline using acetic anhydride [16]. Details of the synthesis reaction of ODAA were given in Section S.5.…”

Section: Synthesis and Standardization Of Odaamentioning

confidence: 99%

“…Then, we decided to synthesize this compound in order to use as a reference standard in our study. Preparation of ODAA was performed by the acetylation of 4,4 ′oxydianiline using acetic anhydride as described [16]. Thin-layer chromatography (TLC) results showed that the synthesis reaction of ODAA completed successfully.…”

Section: Identification Of Odaa In Acetaminophen Batches and Its Subs...mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and standardization of an impurity of acetaminophen, development and validation of liquid chromatographic method

Arıkan

Kulabaş

Küçükgüzel

2023

Journal of Pharmaceutical and Biomedical Analysis

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“…ODAA was synthesized by acetylation of 4,4 ′ -oxydianiline using acetic anhydride [16]. Details of the synthesis reaction of ODAA were given in Section S.5.…”

Section: Synthesis and Standardization Of Odaamentioning

confidence: 99%

Section: Identification Of Odaa In Acetaminophen Batches and Its Subs...mentioning

confidence: 99%

Synthesis and standardization of an impurity of acetaminophen, development and validation of liquid chromatographic method

Arıkan

Kulabaş

Küçükgüzel

2023

Journal of Pharmaceutical and Biomedical Analysis

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“…The benzimidazole groove‐binders 1a (Hoechst 33342) and 1b (Hoechst 33258) can selectively bind to small grooves rich in base pairs to produce cytotoxic effects by inhibiting DNA topoisomerase I and DNA helicase, so Hoechst 33342 and Hoechst 33258 as lead compounds have been widely reported (Issar et al, 2015; Singh et al, 1992). Hoechst 33258 showed anti‐L1210 mouse leukemia activity and positive effect in various solid tumors which led to the compound entering phase I clinical trials in humans, such as pancreatic cancer (Mmler et al, 1971; Wang et al, 2014). A subsequent Phase II trial of pancreatic cancer showed that Hoechst 33258 had a therapeutic effect on patients with advanced pancreatic cancer (Kraut et al, 1991; Wang et al, 2018).…”

Section: Introductionmentioning

confidence: 99%

Recent progress of research on anti‐tumor agents using benzimidazole as the structure unit

Peng

Chen

et al. 2022

Chem Biol Drug Des

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With the development of exploration for disease‐related proteins or receptors, more and more novel structural lead compounds are required to designed and synthesized. The benzimidazole is an effective structural unit in which the benzene ring is fused at the 4 and 5 positions of the imidazole ring and wildly used in drug design. Here, we introduce some recent progress of research for anti‐tumor agents which was target to various target proteins such as DNA topoisomerase, angiogenesis, serine/threonine protein kinase, and tyrosine protein kinase. These anti‐tumor agents are all introduced benzimidazole as the structure unit. Further docking study showed that the benzimidazole group was not only act as a skeleton to expand the structure of molecule but also as an excellent ligand unit to form hydrogen bond or π–π conjugation and hydrophobic interaction with target proteins or receptors. We expect that introducing benzimidazole in the chemical structure could be a reasonable and priority strategy in novel anti‐tumor agents' design.

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Sulfated Ceria Catalyzed Synthesis of Imidazopyridines and Their Implementation as DNA Minor Groove Binders

Srinivasan

Rangappa²,

Anilkumar

et al. 2019

Chemistry & Biodiversity

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The small molecules that bind to DNA minor groove are considered as potential therapeutic agents to fight against many human diseases. They induce cell death by interfering with transcription, replication and progression of cell cycle. Herein, we report the synthesis of imidazopyridine‐3‐amines using sulfated ceria catalyst by employing Groebkee–Blackburne–Bienayme reaction. We evaluated the possible antiproliferative and antimycobacterial activity against A549 cells and Mycobacterium tuberculosis, respectively. Among the tested compounds, N‐tert‐butyl‐2‐(2‐butyl‐4‐chloro‐1H‐imidazol‐5‐yl)‐5,7‐dimethylimidazo[1,2‐a]pyridin‐3‐amine (4g) was identified as cytotoxic heterocycle and antimycobacterial agent. Molecular docking studies of the imidazopyridine derivatives revealed the consistent positioning in the minor groove with a tight shape fit between receptor and ligands. Therefore, we speculate that new imidazopyridines induce their pharmacological effect by targeting the minor groove of DNA.

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Design of novel bis-benzimidazole derivatives as DNA minor groove binding agents

Cited by 11 publications

References 14 publications

Synthesis and standardization of an impurity of acetaminophen, development and validation of liquid chromatographic method

Synthesis and standardization of an impurity of acetaminophen, development and validation of liquid chromatographic method

Recent progress of research on anti‐tumor agents using benzimidazole as the structure unit

Sulfated Ceria Catalyzed Synthesis of Imidazopyridines and Their Implementation as DNA Minor Groove Binders

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