Cascade C-H Annulation Reaction of Benzaldehydes, Anilines, and Alkynes toward Dibenzo[ a, f]quinolizinium Salts: Discovery of Photostable Mitochondrial Trackers at the Nanomolar Level

Vilas D Kadam; Boya Feng; Xingyu Chen; Wenbo Liang; Fulin Zhou; Yanhong Liu; Ge Gao; Jingsong You

doi:10.1021/acs.orglett.8b03015

Cascade C-H Annulation Reaction of Benzaldehydes, Anilines, and Alkynes toward Dibenzo[ a, f]quinolizinium Salts: Discovery of Photostable Mitochondrial Trackers at the Nanomolar Level

Org Lett. 2018 Nov 16;20(22):7071-7075. doi: 10.1021/acs.orglett.8b03015. Epub 2018 Oct 26.

Authors

Vilas D Kadam¹, Boya Feng¹, Xingyu Chen¹, Wenbo Liang¹, Fulin Zhou¹, Yanhong Liu¹, Ge Gao¹, Jingsong You¹

Affiliation

¹ Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry , Sichuan University , 29 Wangjiang Road , Chengdu 610064 , P. R. China.

PMID: 30362760
DOI: 10.1021/acs.orglett.8b03015

Abstract

Fluorescent mitochondrial trackers with the dibenzo[ a, f]quinolizinium core are unprecedentedly synthesized by a one-pot protocol starting from commercially available benzaldehydes, anilines, and alkynes through a rhodium(III)-catalyzed cascade C-H N- and C-annulation reaction. Among them, 5g is the most prominent and exhibits high specificity, high efficiency at nanomolar level, superior photostability, and low cytotoxicity.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Alkynes / chemistry*
Aniline Compounds / chemistry*
Benzaldehydes / chemistry*
Catalysis
Cell Culture Techniques
Drug Stability
Fluorescent Dyes / chemical synthesis*
Fluorescent Dyes / chemistry
Hep G2 Cells
Humans
Hydrogen Bonding
Microscopy, Confocal
Mitochondria / ultrastructure*
Nanostructures / chemistry*
Quinolizines / chemical synthesis*
Quinolizines / chemistry
Rhodium / chemistry
Salts

Substances

Alkynes
Aniline Compounds
Benzaldehydes
Fluorescent Dyes
Quinolizines
Salts
Rhodium