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Medicinal Chemistry Research

, Volume 24, Issue 6, pp 2476–2484 | Cite as

Synthesis and evaluation of linear furanocoumarins as potential anti-breast and anti-prostate cancer agents

  • Siddheshwar K. Chauthe
  • Shivani Mahajan
  • Mahesh Rachamalla
  • Kulbhushan Tikoo
  • Inder P. SinghEmail author
Original Research

Abstract

A series of 22 furanocoumarin derivatives were synthesized and evaluated for cytotoxicity against breast cancer (MCF-7 and MDA-MB-231) and prostate cancer (PC-3) cell lines along with normal cell line. Several analogs were synthesized by replacing prenyl moiety with alkyl, aromatic, and heteroaromatic functionality to study the structure–activity relationship. Compounds 20 and 22 with adamantoylamino, diprenylamino and substituted benzene sulfonamide substituents showed potent antiproliferative activity in MCF-7 cell line with IC50 values of 0.48 and 0.53 µM, respectively. Both the compounds showed higher IC50 value in MCF-10A cell lines indicating nontoxicity in normal cell lines.

Keywords

Anticancer Breast cancer Cytotoxic Furanocoumarin Imperatorin Prostate cancer 

Abbreviations

TBAB

Tetrabutylammonium bromide

FBS

Fetal bovine serum

MTT

Methylthiazolyl tetrazolium assay

SAR

Structure–activity relationship

DMEM

Dulbecco’s modified Eagle medium

EDTA

Ethylenediaminetetraacetic acid

Notes

Acknowledgments

SKC is thankful to the Council of Scientific and Industrial Research, India for fellowship. The authors are thankful to the Director of NIPER for extending support to this work.

Conflict of interest

Authors declared no conflict of interest.

Supplementary material

44_2014_1312_MOESM1_ESM.doc (3.3 mb)
Supplementary material 1.Spectral data for the compounds 611, 1417, and 24 are provided in supplementary information. (DOC 3370 kb)

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • Siddheshwar K. Chauthe
    • 1
  • Shivani Mahajan
    • 1
  • Mahesh Rachamalla
    • 2
  • Kulbhushan Tikoo
    • 2
  • Inder P. Singh
    • 1
    Email author
  1. 1.Department of Natural ProductsNational Institute of Pharmaceutical Education and Research (NIPER)PunjabIndia
  2. 2.Department of Pharmacology and ToxicologyNational Institute of Pharmaceutical Education and Research (NIPER)PunjabIndia

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