Synthesis and cytotoxicity of Baylis-Hillman template derived betulinic acid-triazole conjugates. Issue 29 (20th July 2017)

• Record Type: Journal Article
• Authors: Suman, Pathi; Patel, Amardeep; Solano, Lucas; Jampana, Gayathri; Gardner, Zachary S.; Holt, Crystal M.; Jonnalagadda, Subash C.
• Is Part Of: Tetrahedron. Volume 73:Issue 29(2017)
• Page Start: 4214
• Page End: 4226
• Publication Date: 2017-07-20
• Subjects: Betulin -- Betulinic acid -- Baylis-Hillman reaction -- Click reaction -- Triazole -- Cycloaddition; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2016.11.056
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: Several alkynes and azides were prepared starting from betulinic acid and Baylis-Hillman reaction-derived allylic alcohols. These alkynes and azides were then coupled under click cycloaddition conditions to obtain functionalized betulinic acid-triazole conjugates. Similarly, pyrazinyl- and indolylbetulinic acid-triazoles were also prepared employing cycloaddition chemistry. All the synthetic compounds were tested for their cytotoxicity against murine breast cancer (4T1) and human pancreatic cancer (MIA PaCa-2) cell lines. Based on these in vitro assays, two series of compounds have been identified as lead compounds for further development. Graphical abstract: