Ru(II)-Catalyzed C(sp2)–H Activation
Annulation: Synthesis of Fluorescent Benzoisoquinolonyl Acetate/Peptides
from N‑Arylamides and Ethyne at Room Temperature
Posted on 2024-05-16 - 03:43
Benzoisoquinolones are aryl ring
extended isoquinolinone derivatives,
which are constituents of alkaloid natural products. This report describes
the synthesis of novel benzoisoquinolone amino acid/peptide derivatives
from the respective N-aryl amino esters/peptides
through Ru-catalyzed C(sp2)–H annulation at room
temperature. The N-terminal amide acts as an intrinsic
directing group and coordinates with the active Ru(II) catalyst for
the C–H bond activation and annulation of the aryl ring to
produce benzoisoqunolone derivatives. Importantly, these benzoisoquinolinones
exhibit fluorescence (QY ∼35%) in protic polar solvents, possibly
due to charge transfer, and exhibit cell internalization to the cell
nucleus without any significant cytotoxicity to human cell lines (HEK293T).
Hence, our results are exceptional to transform standard amino acids/peptides
into fluorescent peptides at room temperature in the late stage, which
could be applicable for tracking specific target peptides by fluorescence
microscopy.
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Gupta, Manish
K.; Panda, Ankita; Sharma, Nagendra K. (1753). Ru(II)-Catalyzed C(sp2)–H Activation
Annulation: Synthesis of Fluorescent Benzoisoquinolonyl Acetate/Peptides
from N‑Arylamides and Ethyne at Room Temperature. ACS Publications. Collection. https://doi.org/10.1021/acs.joc.4c00048