Synthesis and cytotoxicity of novel imidazo[4,5- d ]azepine compounds derived from marine natural product ceratamine A

Pan, Xuan; Tao, Lulu; Ji, Ming; Chen, Xiaoguang; Liu, Zhanzhu

doi:10.1016/j.bmcl.2018.02.004

Cited by 9 publications

(4 citation statements)

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“…Aplysamine-1 ( 7 ) was shown to be a weak H 3 receptor antagonist compared to a standard of conessine achieving an IC 50 value of 0.34 μg/mL (0.83 μM) [ 167 ]. Compounds 24 and 25 (ceratamine A and B, respectively) are cytotoxic and antimitotic in a variety of assays covering a number of human and rat cell lines [ 168 , 169 , 170 ]. Compound 28 was assessed as being a potent antifungal agent against the fungus Geotrichum candidum [ 171 ].…”

Section: Resultsmentioning

confidence: 99%

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

et al. 2021

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This study provides a review of all isolated natural products (NPs) reported for sponges within the order Verongiida (1960 to May 2020) and includes a comprehensive compilation of their geographic and physico-chemical parameters. Physico-chemical parameters were used in this study to infer pharmacokinetic properties as well as the potential pharmaceutical potential of NPs from this order of marine sponge. In addition, a network analysis for the NPs produced by the Verongiida sponges was applied to systematically explore the chemical space relationships between taxonomy, secondary metabolite and drug score variables, allowing for the identification of differences and correlations within a dataset. The use of scaffold networks as well as bipartite relationship networks provided a platform to explore chemical diversity as well as the use of chemical similarity networks to link pharmacokinetic properties with structural similarity. This study paves the way for future applications of network analysis procedures in the field of natural products for any order or family.

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Section: Resultsmentioning

confidence: 99%

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

et al. 2021

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“…The phosphoamidate prodrug of compound 257 was 1.6-to 17.7-fold less active than 257 itself against the cancer cell lines, leading the authors to speculate that anticancer action is through inhibition of S-adenosylhomocysteine hydrolase by 257 rather than interference with DNA or RNA polymerase by the triphosphorylated metabolite of 257. A novel series of imidazoazepine derivatives inspired by the natural product ceratamine A (259) was synthesized by Pan et al [204]. The key step in the synthesis was the formation of the imidazoazepine core (scaffold 261) via an intramolecular Heck reaction starting from 260.…”

Section: Natural Product Imidazole Derivativesmentioning

confidence: 99%

“…A novel series of imidazoazepine derivatives inspired by the natural product ceratamine A ( 259 ) was synthesized by Pan et al [ 204 ]. The key step in the synthesis was the formation of the imidazoazepine core (scaffold 261 ) via an intramolecular Heck reaction starting from 260 .…”

Section: Anticancer Activities Shown By Imidazole Derivatives Through Undefined Mechanismsmentioning

confidence: 99%

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

et al. 2021

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Nitrogen-containing heterocyclic rings are common structural components of marketed drugs. Among these heterocycles, imidazole/fused imidazole rings are present in a wide range of bioactive compounds. The unique properties of such structures, including high polarity and the ability to participate in hydrogen bonding and coordination chemistry, allow them to interact with a wide range of biomolecules, and imidazole-/fused imidazole-containing compounds are reported to have a broad spectrum of biological activities. This review summarizes recent reports of imidazole/fused imidazole derivatives as anticancer agents appearing in the peer-reviewed literature from 2018 through 2020. Such molecules have been shown to modulate various targets, including microtubules, tyrosine and serine-threonine kinases, histone deacetylases, p53-Murine Double Minute 2 (MDM2) protein, poly (ADP-ribose) polymerase (PARP), G-quadraplexes, and other targets. Imidazole-containing compounds that display anticancer activity by unknown/undefined mechanisms are also described, as well as key features of structure-activity relationships. This review is intended to provide an overview of recent advances in imidazole-based anticancer drug discovery and development, as well as inspire the design and synthesis of new anticancer molecules.

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“…Derivative 15d showed relatively good anticancer activity with the IC 50 = 23 µM (IC 50 of 15a was equal to 26.5 µM) in cells from lung carcinoma (A549 cell line) [ 159 ]. A much more significant increase in the antiproliferative activity was observed for derivative 15e (IC 50 in A549 cells of 8.56 µM) with a benzyl group at the N-7 and substitution with three methoxy groups on the benzene ring [ 160 ].…”

Section: Microtubule Inhibitorsmentioning

confidence: 99%

Mitotic Poisons in Research and Medicine

et al. 2020

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Cancer is one of the greatest challenges of the modern medicine. Although much effort has been made in the development of novel cancer therapeutics, it still remains one of the most common causes of human death in the world, mainly in low and middle-income countries. According to the World Health Organization (WHO), cancer treatment services are not available in more then 70% of low-income countries (90% of high-income countries have them available), and also approximately 70% of cancer deaths are reported in low-income countries. Various approaches on how to combat cancer diseases have since been described, targeting cell division being among them. The so-called mitotic poisons are one of the cornerstones in cancer therapies. The idea that cancer cells usually divide almost uncontrolled and far more rapidly than normal cells have led us to think about such compounds that would take advantage of this difference and target the division of such cells. Many groups of such compounds with different modes of action have been reported so far. In this review article, the main approaches on how to target cancer cell mitosis are described, involving microtubule inhibition, targeting aurora and polo-like kinases and kinesins inhibition. The main representatives of all groups of compounds are discussed and attention has also been paid to the presence and future of the clinical use of these compounds as well as their novel derivatives, reviewing the finished and ongoing clinical trials.

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Synthesis and cytotoxicity of novel imidazo[4,5- d ]azepine compounds derived from marine natural product ceratamine A

Cited by 9 publications

References 9 publications

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

Application of Networking Approaches to Assess the Chemical Diversity, Biogeography, and Pharmaceutical Potential of Verongiida Natural Products

Imidazoles as Potential Anticancer Agents: An Update on Recent Studies

Mitotic Poisons in Research and Medicine

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