Synthesis and biological activity of pyrazole analogues of the staurosporine aglycon K252c

Esvan, Yannick J.; Giraud, F; Pereira, Elisabeth; Suchaud, Virginie; Nauton, Lionel; Théry, Vincent; Dezhenkova, Lyubov G.; Kaluzhny, Dmitry N.; Mazov, Vsevolod N.; Shtil, Alexander A.; Anizon, Fabrice; Moreau, Pascale

doi:10.1016/j.bmc.2016.05.032

Cited by 18 publications

(14 citation statements)

References 27 publications

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“…A strong lead candidate, compound 47 (Figure 58), was synthesized from staurosporine aglycone (K252c) 90 . The structure–activity relationship showed that compound 47 is a powerful tropomyosine kinase TrkA inhibitor; therefore, it was selected as a proof of concept for in vitro and in vivo studies 53 .…”

Section: Hexacyclic Fused Carbazolesmentioning

confidence: 99%

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Issa

Prandina

Bedel

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

111

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For over half a century, the carbazole skeleton has been the key structural motif of many biologically active compounds including natural and synthetic products. Carbazoles have taken an important part in all the existing anti-cancer drugs because of their discovery from a large variety of organisms, including bacteria, fungi, plants, and animals. In this article, we specifically explored the literature from 2012 to 2018 on the anti-tumour activities reported to carbazole derivatives and we have critically collected the most significant data. The most described carbazole anti-tumour agents were classified according to their structure, starting from the tricyclic–carbazole motif to fused tetra-, penta-, hexa- and heptacyclic carbazoles. To date, three derivatives are available on the market and approved in cancer therapy.

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Section: Hexacyclic Fused Carbazolesmentioning

confidence: 99%

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

Issa

Prandina

Bedel

et al. 2019

Journal of Enzyme Inhibition and Medicinal Chemistry

111

View full text Add to dashboard Cite

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“…Sulfonamide 18 was purchased from ChemBridge. tert -Butyl 3-(chlorocarbonyl)-1 H -indole-1-carboxylate was prepared using a literature procedure . 6-Methoxy-2-pyridinecarbonyl chloride was prepared using a literature procedure .…”

Section: Methodsmentioning

confidence: 99%

Modular Synthesis of 3,6-Disubstituted-1,2,4-triazines via the Cyclodehydration of β-Keto-N-acylsulfonamides with Hydrazine Salts

et al. 2018

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A straightforward method for preparing 3,6-disubstituted-1,2,4-triazines through a redox-efficient cyclodehydration of β-keto- N-acylsulfonamides with hydrazine salts is described. Two approaches for synthesizing the requisite β-keto- N-acylsulfonamides are presented, which allow for the late stage incorporation of either the C3 or C6 substituent in a flexible manner from acid chlorides or α-bromoketones, respectively. The scope of this methodology includes primary and secondary sp-linked substituents at both the C3 and C6 positions, and the mild reaction conditions tolerate a variety of sensitive functionalities.

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“…73 The cytotoxicity has been evaluated toward colon carcinoma HCT116 and leukemia K562 cultured human tumor cells. 74 Other pyrazole drugs with biological activities are Rimonabant, which functions as a cannabinoid receptor and is utilized to treat obesity, Celecoxib, which inhibits COX-2, Fomepizole, an alcohol dehydrogenase inhibitor and Sildenal, which selectively inhibits phosphodiesterase type 5. 75 Recently, pyrazole derivatives with 5-phenyl-2-furan substitutions were synthesized by Ahmed et.…”

Section: Medicinal Applicationsmentioning

confidence: 99%