Synthesis and cytotoxicity of Baylis-Hillman template derived betulinic acid-triazole conjugates

Pathi Suman, Amardeep Patel, Lucas Solano, Gayathri Jampana, Zachary S. Gardner, Crystal M. Holt, Subash C. Jonnalagadda

Research output: Contribution to journalArticle

16 Scopus citations

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.

Original languageEnglish (US)
Pages (from-to)4214-4226
Number of pages13
JournalTetrahedron
Volume73
Issue number29
DOIs
StatePublished - Jan 1 2017

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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