Design, click synthesis, anticancer screening and docking studies of novel benzothiazole-1,2,3-triazoles appended with some bioactive benzofused heterocycles

Aouad, Mohamed Reda; Almehmadi, Meshal A.; Rezki, Nadjet; Al-blewi, Fawzia Faleh; Messali, Mouslim; Ali, Imran

doi:10.1016/j.molstruc.2019.04.005

Cited by 60 publications

(41 citation statements)

References 52 publications

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“…Recently, benzothiazole scaffold has been an attractive subject due to its potently anticancer activity in medicinal chemistry [10][11][12] .…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative benzothiazoles incorporating a trimethoxyphenyl scaffold as novel colchicine site tubulin polymerisation inhibitors

Liu

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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Tubulin polymerisation inhibitors exhibited an important role in the treatment of patients with prostate cancer. Herein, we reported the medicinal chemistry efforts leading to a new series of benzothiazoles by a bioisosterism approach. Biological testing revealed that compound 12a could significantly inhibit in vitro tubulin polymerisation of a concentration dependent manner, with an IC 50 value of 2.87 lM. Immunofluorescence and EBI competition assay investigated that compound 12a effectively inhibited tubulin polymerisation and directly bound to the colchicine-binding site of b-tubulin in PC3 cells. Docking analysis showed that 12a formed hydrogen bonds with residues Tyr357, Ala247 and Val353 of tubulin. Importantly, it displayed the promising antiproliferative ability against C42B, LNCAP, 22RV1 and PC3 cells with IC 50 values of 2.81 lM, 4.31 lM, 2.13 lM and 2.04 lM, respectively. In summary, compound 12a was a novel colchicine site tubulin polymerisation inhibitor with potential to treat prostate cancer. A novel colchicine site tubulin polymer ization inhibitor Time/minutesFluorescence intensity

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“…Recently, benzothiazole scaffold has been an attractive subject due to its potently anticancer activity in medicinal chemistry [10][11][12] .…”

Section: Introductionmentioning

confidence: 99%

Antiproliferative benzothiazoles incorporating a trimethoxyphenyl scaffold as novel colchicine site tubulin polymerisation inhibitors

Liu

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…The 1,2,3‐triazole tethered isatin–benzothiazole hybrids 20 (IC 50 : >10 μM, MTT assay) were devoid of activity against SW182 and H199 cancer cells, [ 77 ] whereas movement of benzothiazole to C‐3 position of isatin moiety was beneficial for the activity and hybrids 21 (GI 50 : 10.92–94.64 μM, SRB assay) showed potential activity against MDA‐MB‐468, MDA‐MB‐231, and MCF‐7 breast cancer cell lines. [ 78 ] The SAR demonstrated that the benzothiazole fragment was indispensable for the activity and alkylamino group at the N‐1 position preferred.…”

Section: Isatin–coumarin Hybridsmentioning

confidence: 99%

Recent advances in isatin hybrids as potential anticancer agents

Ding

Zhou

Zeng

2020

Archiv der Pharmazie

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The isatin framework is a useful template for the development of novel anticancer agents. This is exemplified by the fact that several isatin‐based anticancer agents, such as semaxanib, sunitinib, nintedanib, and hesperadin, are already in use or under clinical trials for the treatment of diverse kinds of cancers. Isatin‐based hybrids could be obtained by incorporating other anticancer pharmacophores into the isatin skeleton and they have the potential to overcome drug resistance with reduced side effects. Thus, isatin‐based hybrids may provide attractive scaffolds for the development of novel anticancer agents. This review covers the recent advances of isatin‐based hybrids with anticancer activity, covering articles published between 2001 and 2019. The anticancer activities of these molecules and the structure–activity relationships are also discussed. The purpose of this review article is to set up the direction for the design and development of isatin‐based hybrids with high efficacy and low toxicity.

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“…Based on the above observations and by taking the advantages of MW, we herein report the click synthesis of novel benzothiazole based 1,2,3-triazole moiety by both conventional and microwave irradiation as a valuable addition to our interest on the development of new polyheterocyclic compounds [21][22][23][24][25][26][27][28][29]. Microwave technique has been used in this study because it improves reaction rates, environmentally friendly and operational simplicity [30].…”

Section: Introductionmentioning

confidence: 97%

Green microwave versus conventional synthesis, crystal structure of 1-(4-(Benzothiazol-2-yl)piperazin-1-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethenone and HS-Analysis

Said

Messali

Rezki

et al. 2020

Journal of Taibah University for Science

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This study reports an efficient eco-friendly microwave assisted synthesis of 1-(4-(benzothiazol-2yl)piperazin-1-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethanone (4) through the click cyclocondensation of 2-azido-1-(4-(benzo[d]thiazol-2-yl)piperazin-1-yl)ethanone (3) with phenyl acetylene. The synthesis was carried out under optimized copper catalyst copper(II) sulfate pentahydrate/sodium ascorbate, t-BuOH/water (1:1, v/v) to afford the regioselective 1,4-disubstituted 1,2,3-triazole isomer. The reactions were greatly accelerated using microwave irradiation. The new designed 1,2,3-triazole was fully characterizid by IR, NMR, MS spectral data and X-ray diffraction. The crystal structure of 4 demonstrated a conventional chair conformation for the piperazine ring. Interesting Hirshfeld Surface Analysis (HAS) was conducted showing clear agreement with the XRD analysis.

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Design, click synthesis, anticancer screening and docking studies of novel benzothiazole-1,2,3-triazoles appended with some bioactive benzofused heterocycles

Cited by 60 publications

References 52 publications

Antiproliferative benzothiazoles incorporating a trimethoxyphenyl scaffold as novel colchicine site tubulin polymerisation inhibitors

Antiproliferative benzothiazoles incorporating a trimethoxyphenyl scaffold as novel colchicine site tubulin polymerisation inhibitors

Recent advances in isatin hybrids as potential anticancer agents

Green microwave versus conventional synthesis, crystal structure of 1-(4-(Benzothiazol-2-yl)piperazin-1-yl)-2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethenone and HS-Analysis

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