2. Academic Validation
  3. Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in vitro exploration for therapeutic potential against HeLa cancer cell lines

Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in vitro exploration for therapeutic potential against HeLa cancer cell lines

  • Eur J Med Chem. 2017 Jan 27:126:870-878. doi: 10.1016/j.ejmech.2016.12.022.
Nitin P Lad 1,  Sarang Kulkarni 2,  Rajiv Sharma 2,  Malcolm Mascarenhas 2,  Mahesh R Kulkarni 1,  Shivaji S Pandit 3
Affiliations

Affiliations

  • 1 Research Centre and Post Graduate Department of Chemistry, Padmashri Vikhe Patil College of Arts, Science and Commerce, Pravaranagar, A/P Loni, Tal. Rahata, Dist. Ahmednagar 413713, India; Department of Medicinal Chemistry, Piramal Enterprises Ltd., 1-Nirlon Complex, Goregaon (East), Mumbai 400063, India.
  • 2 Department of Medicinal Chemistry, Piramal Enterprises Ltd., 1-Nirlon Complex, Goregaon (East), Mumbai 400063, India.
  • 3 Research Centre and Post Graduate Department of Chemistry, Padmashri Vikhe Patil College of Arts, Science and Commerce, Pravaranagar, A/P Loni, Tal. Rahata, Dist. Ahmednagar 413713, India. Electronic address: akankshapandit2002@yahoo.com.
PMID: 27987486 DOI: 10.1016/j.ejmech.2016.12.022
Abstract

A novel modification of piperlongumine is designed, bearing a cyclic sulphonamide (sultam) and its synthesis is described. For the first time herein we report the synthesis and biological evaluation of the natural product derived cyclic sulfonamides using Grubbs second generation catalyst (Grubbs II) via ring closing metathesis approach. Synthesis of a series of piperlongumine derived sultams is done in a moderate to good yield using Wittig reaction, Ring-Closing Metathesis (RCM) and, amide synthesis by using mixed anhydride, approach. All synthesized compounds were evaluated for Anticancer activity and some demonstrated dose dependent reduction in HeLa cell growth. Of these 7, 10 and 14 significantly reduced the cell growth. Consequently their calculated GI50 values were found to be 0.1 or <0.1 μM.

Keywords

Anticancer; GI(50) values; Piperlongumine (PL) derived cyclic sulfonamide (sultams); Ring closing metathesis.

Figures