Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 1,2,3-triazole moiety as c-Met kinase inhibitors

Tang, Qidong; Wang, Linxiao; Tu, Yayi; Zhu, Wufu; Luo, Rong; Tu, Qidong; Wang, Ping; Wu, Chunjiang; Gong, Ping; Zheng, Pengwu

doi:10.1016/j.bmcl.2016.02.059

Cited by 41 publications

(14 citation statements)

References 19 publications

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“…Based on the structural characteristics of type II c-Met inhibitors, we can obtain a general feature which can be divided into four units of A-D 20 (Fig. 2).…”

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confidence: 99%

Imidazopyridine hydrazone derivatives exert antiproliferative effect on lung and pancreatic cancer cells and potentially inhibit receptor tyrosine kinases including c-Met

Damghani

Moosavi

Khoshneviszadeh

et al. 2021

Sci Rep

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Aberrant activation of c-Met signalling plays a prominent role in cancer development and progression. A series of 12 imidazo [1,2-α] pyridine derivatives bearing 1,2,3-triazole moiety were designed, synthesized and evaluated for c-Met inhibitory potential and anticancer effect. The inhibitory activity of all synthesized compounds against c-Met kinase was evaluated by a homogeneous time-resolved fluorescence (HTRF) assay at the concentration range of 5–25 µM. Derivatives 6d, 6e and 6f bearing methyl, tertiary butyl and dichloro-phenyl moieties on the triazole ring, respectively, were the compounds with the highest potential. They significantly inhibited c-Met by 55.3, 53.0 and 51.3%, respectively, at the concentration of 25 µM. Synthetic compounds showed antiproliferative effects against lung (EBC-1) and pancreatic cancer cells (AsPc-1, Suit-2 and Mia-PaCa-2) expressing different levels of c-Met, with IC50 values as low as 3.0 µM measured by sulforhodamine B assay. Active derivatives significantly blocked c-Met phosphorylation, inhibited cell growth in three-dimensional spheroid cultures and also induced apoptosis as revealed by Annexin V/propidium iodide flow cytometric assay in AsPc-1 cells. They also inhibited PDGFRA and FLT3 at 25 µM among a panel of 16 kinases. Molecular docking and dynamics simulation studies corroborated the experimental findings and revealed possible binding modes of the select derivatives with target receptor tyrosine kinases. The results of this study show that some imidazopyridine derivatives bearing 1,2,3-triazole moiety could be promising molecularly targeted anticancer agents against lung and pancreatic cancers.

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“…Based on the structural characteristics of type II c-Met inhibitors, we can obtain a general feature which can be divided into four units of A-D 20 (Fig. 2).…”

mentioning

confidence: 99%

Imidazopyridine hydrazone derivatives exert antiproliferative effect on lung and pancreatic cancer cells and potentially inhibit receptor tyrosine kinases including c-Met

Damghani

Moosavi

Khoshneviszadeh

et al. 2021

Sci Rep

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“…Although a considerable number of synthetic methods are available in the literature, the search for new 1,2,3‐triazoles bearing different functional groups as promising candidates to medicines is still required. In this sense, pyridine and its derivatives combined to triazole cores have been recently studied as cytotoxic agents, antileishmanial, antimicrobial and anti‐inflamatorials . Besides, the incorporation of a chalcogen atom in a carbon chain modifies their physico‐chemical properties, which in pharmacological terms, can dramatically increase the native biological activity of a bioactive molecule, as showed by our group…”

Section: Introductionmentioning

confidence: 84%

Et₂NH‐Mediated 1,3‐Dipolar Cycloaddition: Synthesis of 1‐(2‐(Organylselanyl)pyridin‐3‐yl)‐1H‐1,2,3‐triazole‐4‐carboxylate Derivatives

et al. 2017

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The use of Et 2 NH as organocatalyst for 1,3-dipolar cycloadditions of 3-azido-2-organylselanyl-pyridines with 1,3dicarbonyl compounds is reported in this work. Reactions were conducted using DMSO as solvent at room temperature in air. All products were obtained in good to excellent yields. The reaction took place under very mild conditions and tolerated a range of functionalities. 1-(2-(Phenylselanyl)pyridin-3-yl)-1H-1,2,3-triazole-4-carboxylate containing an alkyne substituent was selected as candidate for a Cu-catalyzed azide alkyne cycloaddition reaction, affording the bis-triazole in good yields.

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“…Tang et al . have synthesized a range of new pyrrolo[2,3‐ b ]pyridine derivatives containing triazole scaffold by this procedure that a mixture of chloropyrrolopyridine ( 128 ), substituted‐nitrophenol ( 129 ) and N,N‐diisopropylethylamine was heated at 200 °C in 1‐methyl‐2‐pyrrolidinone (NMP) under microwave irradiation to prepare compounds 130 .…”

Section: 4‐disubstituted‐123‐triazoles As Anti‐cancer Agentsmentioning

confidence: 99%

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

Mashayekh

Shiri

2019

ChemistrySelect

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The click chemistry is one of the most powerful CÀ N bond forming-reactions towards five-membered heterocycles. The copper-catalyzed azide-alkyne cycloaddition (CuAAC) has widely used in the discovery of anti-cancer drugs and many articles have been published in this field. This review article aims to review general mechanism aspects and the recent advances (2016-2019) of click chemistry for cancer therapy.

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Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 1,2,3-triazole moiety as c-Met kinase inhibitors

Cited by 41 publications

References 19 publications

Imidazopyridine hydrazone derivatives exert antiproliferative effect on lung and pancreatic cancer cells and potentially inhibit receptor tyrosine kinases including c-Met

Imidazopyridine hydrazone derivatives exert antiproliferative effect on lung and pancreatic cancer cells and potentially inhibit receptor tyrosine kinases including c-Met

Et₂NH‐Mediated 1,3‐Dipolar Cycloaddition: Synthesis of 1‐(2‐(Organylselanyl)pyridin‐3‐yl)‐1H‐1,2,3‐triazole‐4‐carboxylate Derivatives

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

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Discovery of novel pyrrolo[2,3-b]pyridine derivatives bearing 1,2,3-triazole moiety as c-Met kinase inhibitors

Cited by 41 publications

References 19 publications

Imidazopyridine hydrazone derivatives exert antiproliferative effect on lung and pancreatic cancer cells and potentially inhibit receptor tyrosine kinases including c-Met

Imidazopyridine hydrazone derivatives exert antiproliferative effect on lung and pancreatic cancer cells and potentially inhibit receptor tyrosine kinases including c-Met

Et2NH‐Mediated 1,3‐Dipolar Cycloaddition: Synthesis of 1‐(2‐(Organylselanyl)pyridin‐3‐yl)‐1H‐1,2,3‐triazole‐4‐carboxylate Derivatives

An Overview of Recent Advances in the Applications of Click Chemistry in the Synthesis of Bioconjugates with Anticancer Activities

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Et₂NH‐Mediated 1,3‐Dipolar Cycloaddition: Synthesis of 1‐(2‐(Organylselanyl)pyridin‐3‐yl)‐1H‐1,2,3‐triazole‐4‐carboxylate Derivatives