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Oxadiazole-substituted naphtho[2,3-b]thiophene-4,9-diones as Potent Inhibitors of Keratinocyte Hyperproliferation. Structure-activity Relationships of the Tricyclic Quinone Skeleton and the Oxadiazole Substituent

Oxadiazole-substituted naphtho[2,3-b]thiophene-4,9-diones as Potent Inhibitors of Keratinocyte Hyperproliferation. Structure-activity Relationships of the Tricyclic Quinone Skeleton and the Oxadiazole Substituent

Atila Basoglu, Simone Dirkmann, Nader Zahedi Golpayegani, Silke Vortherms, Jan Tentrop, Dominica Nowottnik, Helge Prinz, Roland Fröhlich, Klaus Müller

Eur J Med Chem. 2017 Jul 7;134:119-132.

PMID: 28410493

Abstract:

Novel analogues of oxadiazole-substituted naphtho[2,3-b]thiophene-4,9-diones were synthesized in which the tricyclic quinone skeleton was systematically replaced with simpler moieties, such as structures with fewer rings and open-chain forms, while the oxadiazole ring was maintained. In addition, variants of the original 1,2,4-oxadiazole ring were explored. Overall, the complete three-ring quinone was essential for potent suppression of human keratinocyte hyperproliferation, whereas analogous anthraquinones were inactive. Also, the oxadiazole ring per se was not sufficient to elicit activity. However, rearrangement of the heteroatom positions in the oxadiazole ring resulted in highly potent inhibitors with compound 24b being the most potent analogue of this series showing an IC50 in the nanomolar range. Furthermore, experiments in isolated enzymatic assays as well as in the keratinocyte-based hyperproliferation assay did not support a major role of redox cycling in the mode of action of the compounds.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP551907643	Thiophene-4		551907-64-3	Price

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