Synthesis and cytotoxic evaluation of novel ester-triazole-linked triterpenoid-AZT conjugates

  • Bioorg Med Chem Lett. 2014 Nov 15;24(22):5190-4. doi: 10.1016/j.bmcl.2014.09.079.
Tuyet Anh Dang Thi  1 ,  Nguyen Thi Kim Tuyet  1 ,  Chinh Pham The  1 ,  Ha Thanh Nguyen  1 ,  Cham Ba Thi  1 ,  Tien Doan Duy  1 ,  Matthias D'hooghe  2 ,  Tuyen Van Nguyen  3
Affiliations
  • 1. Institute of Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam.
  • 2. SynBioC Research Group, Department of Sustainable Organic Chemistry and Technology, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium.
  • 3. Institute of Chemistry, Vietnam Academy of Science and Technology, 18-Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam. Electronic address: [email protected].
PMID: 25442310 DOI: 10.1016/j.bmcl.2014.09.079
Abstract

Betulinic acid and analogous naturally occurring triterpenoid acids were transformed into the corresponding propargyl esters and subsequently deployed as substrates for a click chemistry-mediated coupling with azidothymidine (AZT) en route to novel 1,2,3-triazole-tethered triterpenoid-AZT conjugates. Twelve new hybrids were thus prepared and assessed in terms of their cytotoxic activity, revealing an interesting Anticancer activity of five triterpenoid-AZT hybrids on KB and Hep-G2 tumor cell lines.

Keywords
AZT; Cytotoxic agents; Hybrids; Triterpenoids.