Synthesis and bioevaluation of N,4-diaryl-1,3-thiazole-2-amines as tubulin inhibitors with potent antiproliferative activity

Sun, Maolin; Xu, Qile; Xu, Jingwen; Wu, Yue; Zuo, Daiying; Guan, Qı; Bao, Kai; Wang, Jian; Wu, Yingliang; Zhang, Weige

doi:10.1371/journal.pone.0174006

Cited by 24 publications

(18 citation statements)

References 28 publications

(27 reference statements)

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“…Sun et al [4] synthesized a series of N,4-diaryl-1,3-thiazole-2-amines containing three aromatic rings with an amino linker. Compound 1 (Figure 2) was the most cytotoxic agent with IC 50 values at the submicromolar level.…”

Section: Thiazole Rings Decorated With Different Fragments 21 Thiazomentioning

confidence: 99%

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Ramos-Inza¹,

Aydillo²,

Sanmartín³

et al. 2020

Heterocycles - Synthesis and Biological Activities

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Currently, cancer is one of the major health problems of the human population and prominent cause of death. Thiazole ring has demonstrated many pharmacological activities including anticancer. This scaffold has been found alone or incorporated into the diversity of therapeutic active agents such as tiazofurin, dasatinib, and bleomycin, which are well-known antineoplastic drugs. Recently, most of the compounds isolated from natural sources containing thiazole moiety exhibit notable cytotoxicities and present antitumor potential. In this context, several structural changes have been made in the original structure, such as the incorporation of different substituents or the fusion with other carbo-and heterocycles, in order to increase the antitumoral potency. Related to mechanism of action of these derivatives, some of them act through kinase modulation, polymerization inhibition of microtubule, pro-matrix metalloproteinase activation, signal transducer activation of transcription 3, histone deacetylase inhibition, etc.

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Section: Thiazole Rings Decorated With Different Fragments 21 Thiazomentioning

confidence: 99%

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Ramos-Inza¹,

Aydillo²,

Sanmartín³

et al. 2020

Heterocycles - Synthesis and Biological Activities

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“…It's important to note that thiazole could be used as a promising scaffold for the development of anticancer agents [15][16][17] . Over the last few years, numerous thiazole derivatives have been reported to show potent anticancer activity by inhibiting tubulin polymerisation (Figure 1, I-IV) [18][19][20][21] .…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis and biological evaluation of novel thiazole-naphthalene derivatives as potential anticancer agents and tubulin polymerisation inhibitors

Wang

Liu

Fan

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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A novel series of thiazole-naphthalene derivatives as tubulin polymerisation inhibitors were designed, synthesised, and evaluated for the anti-proliferative activities. The majority of the tested compounds exhibited moderate to potent antiproliferative activity on the MCF-7 and A549 cancer cell lines. Among them, compound 5b was found to be the most active compound with IC 50 values of 0.48 ± 0.03 and 0.97 ± 0.13 lM. Moreover, mechanistic studies revealed that 5b significantly inhibited tubulin polymerisation with an IC 50 value of 3.3 mM, as compared to the standard drug colchicine (IC 50 ¼ 9.1 lM). Further cellular mechanism studies elucidated that 5b arrested the cell cycle at G2/M phase and induced apoptosis in MCF-7 cancer cells. Molecular modelling study indicated that 5b binds well to the colchicine binding site of tubulin. In summary, these results suggest that 5b represents a promising tubulin polymerisation inhibitor worthy of further investigation as potential anticancer agents.

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“…According to the docking results, this compound could bind to the binding site of colchicine in tubulin (Fig. 16) [93].…”

Section: Modification Of 2-amine To 2-arylaminomentioning

confidence: 99%

“…A benzamide HDAC inhibitor, MS-275 (93), is reported to be a selective HDAC inhibitor targeting class I HDACs, which is currently in phase II. Furthermore, reported X-ray crystal structure of Dasatinib (5) bound to Abl and MS-275 docked to HDAC1 homolog.…”

Section: Modification Of 2-amine To 2-aminopyrimidinementioning

confidence: 99%

Development and therapeutic potential of 2-aminothiazole derivatives in anticancer drug discovery

Alizadeh

Hashemi

2021

Med Chem Res

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Currently, the development of anticancer drug resistance is significantly restricted the clinical efficacy of the most commonly prescribed anticancer drug. Malignant disease is widely prevalent and considered to be the major challenges of this century, which concerns the medical community all over the world. Consequently, investigating small molecule antitumor agents, which could decrease drug resistance and reduce unpleasant side effect is more desirable. 2-aminothiazole scaffold has emerged as a promising scaffold in medicinal chemistry and drug discovery research. This nucleus is a fundamental part of some clinically applied anticancer drugs such as dasatinib and alpelisib. Literature survey documented that different 2aminothiazole analogs exhibited their potent and selective nanomolar inhibitory activity against a wide range of human cancerous cell lines such as breast, leukemia, lung, colon, CNS, melanoma, ovarian, renal, and prostate. In this paper, we have reviewed the progresses and structural modification of 2-aminothiazole to pursuit potent anticancers and also highlighted in vitro activities and in silico studies. The information will useful for future innovation.

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Synthesis and bioevaluation of N,4-diaryl-1,3-thiazole-2-amines as tubulin inhibitors with potent antiproliferative activity

Cited by 24 publications

References 28 publications

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Thiazole Moiety: An Interesting Scaffold for Developing New Antitumoral Compounds

Design, synthesis and biological evaluation of novel thiazole-naphthalene derivatives as potential anticancer agents and tubulin polymerisation inhibitors

Development and therapeutic potential of 2-aminothiazole derivatives in anticancer drug discovery

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