The uses of cyclohexan-1,4-dione for the synthesis of thiophene derivatives as new anti-proliferative, prostate anticancer, c-Met and tyrosine kinase inhibitors

Mohareb, Rafat M.; Al‐Omran, Fatima; Ibrahim, Rehab Ali

doi:10.1007/s00044-017-2087-3

Cited by 6 publications

(1 citation statement)

References 30 publications

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“…Among the 6-membered oxygen-comprising heterocycles are the 2-Amino-4Hpyrans as they show high potencies as antimicrobial and anticancer agents [7,8]. We were concerned within the recent years through heterocyclic transformations using cyclohexan-1,3dione as starting material involved through many multi-component reactions [9][10][11][12][13]. In addition, a number of hydrazide-hydrazone derivatives have been claimed to possess interesting bioactivity such as antibacterial-antifungal, anticonvulsant, antiinflammatory, antimalarial, analgesic, antiplatelets, antituberculosis and anticancer activities [14][15][16][17][18][19][20][21].…”

Section: Introductionmentioning

confidence: 99%

Novel synthesis of pyran-3-hydrazide derivatives and their uses to the synthesis hydrazide-hydrazone, pyrazole and thiazole derivatives with anticancer activities

Samir¹,

Mohareb²

2022

Bull. Chem. Soc. Eth.

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ABSTRACT. The multi-component reaction of ethyl acetoacetate with each of malononitrile (3) benzaldehyde (1) in ethanol containing triethylamine gave the ethyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate (4). The latter compound reacted with hydrazine hydrate to give the hydrazide derivative 6. Compound 6 underwent a series of hetero-cyclization reactions to give pyrzole, hydraide-hydrazone, thiazole derivatives. The produced compounds tested against cancer cell lines six cancer cell lines and showed that compounds 8b, 10b, 11a, 17a, 21 and 24a were the most cytotoxic compounds. Further tests of the latter compounds toward the five tyrosine kinases and Pim-1 kinase showed that compounds 10b, 21 and 24a were the most potent of the tested compounds and compounds 10a, 11a and 17a were of the highest inhibitions toward Pim-1 kinase. The high inhibitions of most of the tested compounds toward the selected cancer cell lines and the tyrosine kinases encourage for future work to be done. KEY WORDS: Hydrazide, Thiophene, Pyrazole, Pyran, Cytotoxicity, Tyrosine kinases Bull. Chem. Soc. Ethiop. 2021, 35(3), 573-586. DOI: https://dx.doi.org/10.4314/bcse.v35i3.9

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