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Title 

Modeling, synthesis and NMR characterization of novel chimera compounds targeting STAT3

 

새로운 STAT3 저해제의 고안과 합성

Authors 

S Dell'OrtoD MasciocchiS VillaF MeneghettiG CelentanoD BarloccoD ColomboL LegnaniL TomaJeon Yoon-JeingByoung-Mog KwonA AsaiA Gelain

Publisher 

Royal Society of Chemistry

Issue Date 

2014

Citation 

MedChemComm, vol. 5, no. 10, pp. 1651-1657

Abstract 

Signal Transducer and Activator of Transcription 3 (STAT3) is a cytoplasmic factor that mediates intracellular signaling commonly generated at cell surface receptors and transmits it to the nucleus. In previous research studies we synthesized several molecules inhibiting STAT3 and among them oxadiazole MD77 and pyridazinone I showed an interesting activity. For the first one, a direct inhibition mechanism was determined, while I interfered within the STAT3 pathway at a different level. In order to discover novel compounds possibly endowed with an improved activity, we decided to merge their scaffolds on the basis of their calculated conformational properties. Therefore we designed and synthesized the chimera diastereomers 3-oxo-N-(4-(trifluoromethyl)phenyl)-2,3,4,4a,5,6-hexahydrobenzo[h]cinnoline-6-carboxamide (1, 2) and 3-oxo-N-(4-(trifluoromethyl)phenyl)-2,3,5,6-tetrahydrobenzo[h]cinnoline-6-carboxamide (3) as racemate and their enantiomeric separation was performed. Modeling studies and theoretical prediction of [α]D values were carried out beside NMR studies which allowed us to assign 1 and 2 relative configurations.

ISSN 

2040-2503

Link 

http://dx.doi.org/10.1039/c4md00177j

Appears in Collections

1. Journal Articles > Journal Articles

Registered Date

2019-05-02


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