2. Academic Validation
  3. Synthesis and anticancer activity of some novel 5,6-fused hybrids of juglone based 1,4-naphthoquinones

Synthesis and anticancer activity of some novel 5,6-fused hybrids of juglone based 1,4-naphthoquinones

  • Eur J Med Chem. 2014 Aug 18:83:84-91. doi: 10.1016/j.ejmech.2014.06.012.
Uppuluri Venkata Mallavadhani 1,  Chakka Vara Prasad 2,  Shweta Shrivastava 3,  V G M Naidu 3
Affiliations

Affiliations

  • 1 Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India. Electronic address: uvmavadani@yahoo.com.
  • 2 Natural Products Chemistry Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India.
  • 3 Department of Pharmacology & Toxicology, National Institute of Pharmaceutical Education& Research, Hyderabad 500037, India.
PMID: 24953027 DOI: 10.1016/j.ejmech.2014.06.012
Abstract

Six novel 5,6-fused hybrids such as dihydrobenzofuran-quinone (4a and 4b), benzofuran-quinone (5a and 5b) and chromene-quinone (6a and 6b) of juglone based 1,4-naphthoquinones were synthesized by employing a three step protocol with the cyclisation of o-allyl phenol as the key step. The Anticancer activity of the newly synthesized compounds was evaluated in vitro against seven human Cancer cell lines including cervix (ME-180 and HeLa), breast (MCF-7, MDA-MB-453 and MDA-MB-231), prostate (PC-3) and colon (HT-29) by using MTT assay. The screening results showed that majority of the synthesized compounds exhibited significant Anticancer activity. In particular, compounds 6a and 6b showed potent activities than the standard drug etoposide against prostate and breast Cancer cell lines respectively. Flow cytometric analysis revealed that compounds 6a and 6b induced Apoptosis and arrested the cell cycle at G2/M phase in PC-3 and MDA-MB-453 cells respectively.

Keywords

Anticancer activity; Apoptosis; Cell cycle arrest; Juglone; Plumbagin.

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