Synthesis and biological evaluation of 2,5-diaryl-1,3,4-oxadiazole derivatives as novel Src homology 2 domain-containing protein tyrosine phosphatase 2 (SHP2) inhibitors

Meng, Xiangdong; Gao, Lixin; Wang, Zhijia; Feng, Bo; Zhang, Chun; Satheeshkumar, Rajendran; Li, Jia; Zhu, Yu‐Cheng; Zhou, Yubo; Wang, Wen-Long

doi:10.1016/j.bioorg.2021.105384

Cited by 9 publications

(3 citation statements)

References 41 publications

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“…Compound 61 ( Figure 4 ) exhibited SHP2 inhibitory activity with an IC 50 value of 2.73 ± 0.20 µM, with approximately 1.56-fold, 5.26-fold and 7.36-fold selectivity for SHP2 over SHP1, PTP1B and TCPTP, respectively. Further studies confirmed that compound 61 induced apoptosis and inhibited the proliferation of TF-1 cells in vitro by blocking the SHP2/p-STAT3 pathway 65 .…”

Section: Oxadiazolementioning

confidence: 68%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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Oxadiazole is a five-membered heterocyclic compound containing two nitrogen atoms and one oxygen atom. The 1,3,4-oxadiazole and 1,2,4-oxadiazole have favourable physical, chemical, and pharmacokinetic properties, which significantly increase their pharmacological activity via hydrogen bond interactions with biomacromolecules. In recent years, oxadiazole has been demonstrated to be the biologically active unit in a number of compounds. Oxadiazole derivatives exhibit antibacterial, anti-inflammatory, anti-tuberculous, anti-fungal, anti-diabetic and anticancer activities. In this paper, we report a series of compounds containing oxadiazole rings that have been published in the last three years only (2020–2022) as there was no report or their activities described in any article in 2019, which will be useful to scientists in research fields of organic synthesis, medicinal chemistry, and pharmacology.

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Section: Oxadiazolementioning

confidence: 68%

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Wang

Sun

Jia

et al. 2022

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…To explore the interaction mode between small molecule 7a and 3CL pro (PDB code: 6M2N) [ 23 ], we carried out molecular docking by applying AutoDock 4.2 program [ 31 , 32 , 33 , 34 ]. Figure 3 a showed that 7a docked well into the binding pockets S1 and S2 of 3CL pro , in which the S1, S2 sites play a key role in substrate recognition [ 35 ].…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Biochemical Evaluation of 8H-Indeno[1,2-d]thiazole Derivatives as Novel SARS-CoV-2 3CL Protease Inhibitors

Feng

Gao

et al. 2022

Molecules

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The COVID-19 pandemic caused by SARS-CoV-2 is a global burden on human health and economy. The 3-Chymotrypsin-like cysteine protease (3CLpro) becomes an attractive target for SARS-CoV-2 due to its important role in viral replication. We synthesized a series of 8H-indeno[1,2-d]thiazole derivatives and evaluated their biochemical activities against SARS-CoV-2 3CLpro. Among them, the representative compound 7a displayed inhibitory activity with an IC50 of 1.28 ± 0.17 μM against SARS-CoV-2 3CLpro. Molecular docking of 7a against 3CLpro was performed and the binding mode was rationalized. These preliminary results provide a unique prototype for the development of novel inhibitors against SARS-CoV-2 3CLpro.

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“…[30][31] Our group identified some thiadiazole derivatives with inhibitory activities and fluorescence properties. [32][33][34] In recent years, it has been found that benzothiazole πconjugated moiety exhibits good photophysical properties and has attracted wide interest of researchers. [35][36] The novel pyrido[2,1-b] benzothiazole derivatives 15 a-15 d (shown in Figure 1) exhibited remarkable fluorescence intensity with considerably high quantum yields with anti-bacterial and antifungal activities.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Evaluation of Fluorescent Properties of Benzothiazole Derivatives

et al. 2023

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Fluorescence imaging is conducive to establish a bridge between molecular biology and clinical medicine, and provides new tools for disease process research, early diagnosis, and efficacy evaluation, because of the advantages of rapid imaging and nondestructive detection. Herein, a series of fluorescent molecules with thiadiazole, or thiazole, or benzothiazole cores were designed and synthesized to develop more excellent fluorescent molecules in bio‐imaging. According to theoretical and experimental methods, we found that benzothiazole derivative 14 B with conjugate expansion by (4‐aminophenyl) ethynyl group was the most excellent fluorescent molecule among all the investigated compounds and exhibited low cytotoxicity and strong blue and green fluorescence by confocal cell imaging.

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Synthesis and biological evaluation of 2,5-diaryl-1,3,4-oxadiazole derivatives as novel Src homology 2 domain-containing protein tyrosine phosphatase 2 (SHP2) inhibitors

Cited by 9 publications

References 41 publications

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Research progress on the synthesis and pharmacology of 1,3,4-oxadiazole and 1,2,4-oxadiazole derivatives: a mini review

Synthesis and Biochemical Evaluation of 8H-Indeno[1,2-d]thiazole Derivatives as Novel SARS-CoV-2 3CL Protease Inhibitors

Design, Synthesis and Evaluation of Fluorescent Properties of Benzothiazole Derivatives

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