title: Piperlongumine derived cyclic sulfonamides (sultams): Synthesis and in vitro exploration for therapeutic potential against HeLa cancer cell lines.
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 GI50values were found to be 0.1 or <0.1 μM.
authors.affiliation: 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.
authors.forename: Nitin P
authors.initials: NP
authors.lastname: Lad
authors.affiliation: Department of Medicinal Chemistry, Piramal Enterprises Ltd., 1-Nirlon Complex, Goregaon (East), Mumbai 400063, India.
authors.forename: Sarang
authors.initials: S
authors.lastname: Kulkarni
authors.affiliation: Department of Medicinal Chemistry, Piramal Enterprises Ltd., 1-Nirlon Complex, Goregaon (East), Mumbai 400063, India.
authors.forename: Rajiv
authors.initials: R
authors.lastname: Sharma
authors.affiliation: Department of Medicinal Chemistry, Piramal Enterprises Ltd., 1-Nirlon Complex, Goregaon (East), Mumbai 400063, India.
authors.forename: Malcolm
authors.initials: M
authors.lastname: Mascarenhas
authors.affiliation: 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.
authors.forename: Mahesh R
authors.initials: MR
authors.lastname: Kulkarni
authors.affiliation: 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.
authors.forename: Shivaji S
authors.initials: SS
authors.lastname: Pandit
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D049109:Cell Proliferation / Q000187:drug effects; D060326:Chemistry Techniques, Synthetic; D004148:Dioxolanes / Q000737:chemistry*; D015195:Drug Design; D004354:Drug Screening Assays, Antitumor; D006367:HeLa Cells; D006801:Humans; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D010881:Piperidones
chemical_list: D000970:Antineoplastic Agents; D004148:Dioxolanes; D013449:Sulfonamides; C498077:piperlongumine; D010881:Piperidones
keywords: Anticancer; GI(50) values; Piperlongumine (PL) derived cyclic sulfonamide (sultams); Ring closing metathesis