Synthesis and anticancer activities of 3-arylflavone-8-acetic acid derivatives

Yan, Guang-Hua; Li, Xiaofang; Ge, Bing-Chen; Shi, Xiaowen; Chen, Yu‐Fang; Yang, Xuemei; Liu, Shuwen; Zhao, Pei‐Liang; Zhou, Zhong‐Zhen; Zhou, Chun-Qiong; Chen, Wenhua

doi:10.1016/j.ejmech.2014.11.030

Cited by 26 publications

(5 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Our recent research was mainly focused on potential heterocyclic anticancer agents based on different kinds of heterocyclic scaffolds. − Our reported compounds 4 and 5 with purine bridging group displayed promising antitumor activities and lower cytotoxicity in normal cells but weak tubulin polymerization inhibition activity . Nevertheless, the potent biological profile encouraged us to continue our search for high-potency antitumor drugs.…”

mentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking of Arylpyridines as Antiproliferative Agent Targeting Tubulin

Zhang

Tang

et al. 2020

ACS Med. Chem. Lett.

Self Cite

View full text Add to dashboard Cite

Mimicking different pharmacophoric units into one scaffold is a promising structural modification tool to design new drugs with enhanced biological properties. To continue our research on the tubulin inhibitors, the synthesis and biological evaluation of arylpyridine derivatives (9−29) are described herein. Among these compounds, 6-arylpyridines (13−23) bearing benzo[d]imidazole side chains at the 2-position of pyridine ring displayed selective antiproliferative activities against HT-29 cells. More interestingly, 2-trimethoxyphenylpyridines 25, 27, and 29 bearing benzo[d]imidazole and benzo[d]oxazole side chains displayed more broad-spectrum antitumor activities against all tested cancer cell lines. 29 bearing a 6-methoxybenzo[d]oxazole group exhibited comparable activities against A549 and U251 cells to combretastatin A-4 (CA-4) and lower cytotoxicities than CA-4 and 5-Fu. Further investigations revealed 29 displays strong tubulin polymerization inhibitory activity (IC 50 = 2.1 μM) and effectively binds at the colchicine binding site and arrests the cell cycle of A549 in the G2/M phase by disrupting the microtubules network.

show abstract

mentioning

confidence: 99%

Synthesis, Biological Evaluation, and Molecular Docking of Arylpyridines as Antiproliferative Agent Targeting Tubulin

Zhang

Tang

et al. 2020

ACS Med. Chem. Lett.

Self Cite

View full text Add to dashboard Cite

show abstract

Section: Targeted Sar Studies 2013–2021mentioning

confidence: 99%

“…In addition, 16a was able to induce TNF-α production to a higher extent with respect to DMXAA. Later, the same research group synthesized another series of 16-based analogues, in which the 7-methoxy group was removed (17, Figure 11), which was more potent than the previous ones [33]. In particular, while compounds carrying electron withdrawing groups Later, the same research group synthesized another series of 16-based analogues, in which the 7-methoxy group was removed (17, Figure 11), which was more potent than the previous ones [33].…”

Section: Recently Developed Faa Derivativesmentioning

confidence: 99%

“…Later, the same research group synthesized another series of 16-based analogues, in which the 7-methoxy group was removed (17, Figure 11), which was more potent than the previous ones [33]. In particular, while compounds carrying electron withdrawing groups Later, the same research group synthesized another series of 16-based analogues, in which the 7-methoxy group was removed (17, Figure 11), which was more potent than the previous ones [33]. In particular, while compounds carrying electron withdrawing groups on the phenyl rings showed moderate direct cytotoxic activity, methoxy-substituted analogues proved to be endowed with indirect toxicity comparable or higher than the reference DMXAA and to induce TNF-α production, 17a and 17b (Figure 11) being the most interesting compounds.…”

Section: Recently Developed Faa Derivativesmentioning

confidence: 99%

See 1 more Smart Citation

Flavonoid-Inspired Vascular Disrupting Agents: Exploring Flavone-8-Acetic Acid and Derivatives in the New Century

et al. 2021

View full text Add to dashboard Cite

Naturally occurring flavonoids are found as secondary metabolites in a wide number of plants exploited for both medicine and food and have long been known to be endowed with multiple biological activities, making them useful tools for the treatment of different pathologies. Due to the versatility of the scaffolds and the vast possibilities of appropriate decoration, they have also been regarded as fruitful sources of lead compounds and excellent chemical platforms for the development of bioactive synthetic compounds. Flavone-8-acetic acid (FAA) and 5,6-dimethylxanthone acetic acid (DMXAA) emerged for their antitumour potential due to the induction of cytokines and consequent rapid haemorrhagic necrosis of murine tumour vasculature, and different series of derivatives have been designed thereafter. Although the promising DMXAA failed in phase III clinical trials because of strict species-specificity, a boost in research came from the recent identification of the stimulator of interferon genes (STING), responsible for supporting tumoural innate immune responses, as a possible biological target. Consequently, in the last decade a renewal of interest for these flavonoid-based structures was noticed, and novel derivatives have been synthesised and evaluated for a deeper understanding of the molecular features needed for affecting human cells. Undoubtedly, these natural-derived molecules deserve further investigation and still appear attractive in an anticancer perspective.

show abstract

“…Chromone is one of the most common heterocyclic motifs found in a large number of natural products, pharmaceuticals, and materials . In particular, C3-substituted chromones are recently drawing considerable attention as they exhibit a variety of physiological and biological activities, including anti-inflammatory, antidyslipidemic, antioxidant, antimicrobial, antitumor, and anticancer, etc. Thus, numerous efforts have been devoted to developing efficient protocols for the synthesis of C3-substituted chromone derivatives.…”

Section: Introductionmentioning

confidence: 99%

Photoredox-Catalyzed Tandem Cyclization of Enaminones with N-Sulfonylaminopyridinium Salts toward the Synthesis of 3-Sulfonaminated Chromones

Hu,

Diao,

Yuan

et al. 2023

J. Org. Chem.

View full text Add to dashboard Cite

A photoredox-catalyzed intermolecular tandem sulfonamination/cyclization of enaminones was realized by using Naminopyridinium salts as the sulfonaminated reagents without transition-metal catalysts or bases. The reaction exhibits a broad scope and good functional group tolerance, good yields, and regioselectivity. Preliminary mechanistic studies support the radical property of the reaction and the involvement of N-centered radical intermediates.

show abstract

Synthesis and anticancer activities of 3-arylflavone-8-acetic acid derivatives

Cited by 26 publications

References 28 publications

Synthesis, Biological Evaluation, and Molecular Docking of Arylpyridines as Antiproliferative Agent Targeting Tubulin

Synthesis, Biological Evaluation, and Molecular Docking of Arylpyridines as Antiproliferative Agent Targeting Tubulin

Flavonoid-Inspired Vascular Disrupting Agents: Exploring Flavone-8-Acetic Acid and Derivatives in the New Century

Photoredox-Catalyzed Tandem Cyclization of Enaminones with N-Sulfonylaminopyridinium Salts toward the Synthesis of 3-Sulfonaminated Chromones

Contact Info

Product

Resources

About