Functionalization of 9-thioxanthone at the 1-position: From arylamino derivatives to [1]benzo(thio)pyrano[4,3,2-de]benzothieno[2,3-b]quinolines of biological interest

Abstract : Original 1-amino substituted thioxanthone derivatives were easily prepared from the bare heterocycle by a deprotometalation-iodolysis-copper-catalyzed CeN bond formation sequence. This last reaction delivered mono-or/and diarylated products depending on the aniline involved. 1-Amino-9-thioxanthone was also prepared and reacted with 2-iodoheterocycles. Interestingly, while 1-(arylamino)-9-thioxanthones could be isolated, their subsequent cyclization was found to deliver original hexacyclic derivatives of helicoidal nature. Evaluation of their photophysical properties revealed high fluorescence in polar media, indicating potential applications for biological imaging. These compounds being able to inhibit PIM1 kinase, their putative binding mode was examined through molecular modeling experiments. Altogether, these results tend to suggest the discovery of a new family of fluorescent PIM inhibitors and pave the way for their future rational optimization.
Complete list of metadatas

Cited literature [129 references]  Display  Hide  Download

https://hal.archives-ouvertes.fr/hal-02404054
Contributor : Laurent Picot <>
Submitted on : Wednesday, December 18, 2019 - 10:48:58 AM
Last modification on : Friday, February 7, 2020 - 1:27:59 AM

Files

main_thioxanthones_Mongin_corr...
Files produced by the author(s)

Identifiers

Citation

Blandine Baratte, Nahida Mokhtari Brikci-Nigassa, Lionel Nauton, Pascale Moreau, Olivier Mongin, et al.. Functionalization of 9-thioxanthone at the 1-position: From arylamino derivatives to [1]benzo(thio)pyrano[4,3,2-de]benzothieno[2,3-b]quinolines of biological interest. Bioorganic Chemistry, Elsevier, 2020, 94, pp.103347. ⟨10.1016/j.bioorg.2019.103347⟩. ⟨hal-02404054⟩

Share

Metrics

Record views

53

Files downloads

103