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Medicinal Chemistry Research

, Volume 26, Issue 7, pp 1367–1376 | Cite as

Phenacyl group containing amide derivative of dehydroabietylamine exhibiting enhanced cytotoxic activity against PLC and MCF7 cancer cell lines

  • Muhammad Ayaz Mustufa
  • Afshan Aslam
  • Cigdem Ozen
  • Imran Ali Hashmi
  • Naim ul Hasan Naqvi
  • Mehmet Ozturk
  • Firdous Imran Ali
Original Research

Abstract

New amide derivatives of (+)-dehydroabietylamine, tricyclic abietane diterpene amine, were prepared using Zhongping’s protocol. (+)-N-(2-phenyl-acetyl)-dehydroabietylamine derivative (11) demonstrated noticeable growth attenuation of hepatocellular carcinoma cell lines including PLC/PRF/5, SNU475, Hep3B-TR, and Huh7 with IC50 of 7.4 µM, 9.8 µM, 11.7 µM, and 11.8 µM, respectively. A breast cancer cell line MCF7 was the most sensitive against amide 11 with lowest IC50 value (4.8 µM). Low cell confluence and increase in G2/M phase was recorded after 48 and 72 h of treatment of amide 11 on PLC/PRF/5 cell line. Finally, amide 11 has comparatively sufficient therapeutic role due to addition of N-phenacyl group at C-18. Amide 11 demonstrated as potential candidate for future cancer interference and research.

Graphical Abstract

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Keywords

Cancer Dehydroabietylamine Amides Cytotoxic activity NMR spectroscopy FTIR 

Notes

Acknowledgements

One of the authors is thankful to Higher Education Commission of Pakistan for providing fellowship. Muhammad Ayaz Mustufa was supported by a TUBITAK (Turkey) PhD fellowship. This work was partly supported by grants to M.O. from TUBITAK (111T558) and TUBA (Turkish Academy of Sciences).

Conflict of Interest: The authors declared that they have no competing interests.

Compliance with Ethical Standards

Conflict of interest

The authors declare that they have no competing interests.

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Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • Muhammad Ayaz Mustufa
    • 1
    • 4
  • Afshan Aslam
    • 2
  • Cigdem Ozen
    • 3
  • Imran Ali Hashmi
    • 2
  • Naim ul Hasan Naqvi
    • 1
  • Mehmet Ozturk
    • 3
  • Firdous Imran Ali
    • 2
  1. 1.Baqai Institute of Pharmaceutical SciencesBaqai Medical UniversityKarachiPakistan
  2. 2.Depatment of ChemistryUniversity of KarachiKarachiPakistan
  3. 3.Izmir International Biomedicine and Genome Institute, iBG-izmirDokuz Eylül UniversityBalcova-IzmirTurkey
  4. 4.Pakistan Health Research CouncilIslamabadPakistan

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