2. Academic Validation
  3. Novel sesquiterpenes from Schisandra grandiflora: isolation, cytotoxic activity and synthesis of their triazole derivatives using "click" reaction

Novel sesquiterpenes from Schisandra grandiflora: isolation, cytotoxic activity and synthesis of their triazole derivatives using "click" reaction

  • Eur J Med Chem. 2015 Mar 6:92:449-58. doi: 10.1016/j.ejmech.2014.12.040.
B Poornima 1,  Bandi Siva 1,  G Shankaraiah 1,  A Venkanna 1,  V Lakshma Nayak 2,  Sistla Ramakrishna 2,  C Venkat Rao 3,  K Suresh Babu 4
Affiliations

Affiliations

  • 1 Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India.
  • 2 Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.
  • 3 Department of Chemistry, Sri Venkateswara University, Tirupati 517502, India.
  • 4 Natural Products Laboratory, Division of Natural Product Chemistry, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 607, India. Electronic address: suresh@iict.res.in.
PMID: 25594739 DOI: 10.1016/j.ejmech.2014.12.040
Abstract

Phytochemical investigation of hexane extract from the fruits of Schisandra grandiflora afforded three novel Sesquiterpenes (1-3) along with the three known compounds (4-6). The structures of these isolates were determined by extensive analysis of spectroscopic data (1D, 2D NMR). Further, a series of triazole analogues of 3 and 4 were prepared using "Click" reaction protocol. The reaction scheme involving one-carbon homologation of 3 and 4 using the Bestmann-Ohira reagent followed by regioselective Huisgen 1,3-dipolar cycloaddition reaction of various azides leading to the formation of triazole analogues (20a-20k &21a-21c) which is being reported for the first time. All the triazole products were characterized using spectral data analysis. The anti-proliferative activity of the isolates and the synthetic analogues were studied against Hela (Cervical Cancer), A549 (Lung Cancer), DU-145 (Prostate Cancer), MCF-7 (Breast Cancer) and B-16 (Mouse melanoma) Cancer cell lines.

Keywords

Bestmann-Ohira homologation; Click reaction; Schisandra grandiflora; Sesquiterpenes; Triazole derivatives and anti-proliferative activity.

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