Molecules 2015, 20(8), 14638-14655; doi:10.3390/molecules200814638
Synthesis, Characterization, and Anti-Cancer Activity of Some New N′-(2-Oxoindolin-3-ylidene)-2-propylpentane hydrazide-hydrazones Derivatives
Ayman El-Faham 1,2,*
, Muhammad Farooq 3,*
, Sherine N. Khattab 2, Nael Abutaha 3, Mohammad A. Wadaan 3, Hazem A. Ghabbour 4
and Hoong-Kun Fun 4,5
and Hoong-Kun Fun 4,51
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
2
Department of Chemistry, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, Egypt
3
Department of Zoology, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
4
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
5
Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia
*
Authors to whom correspondence should be addressed.
Academic Editor: Jean Jacques Vanden Eynde
Received: 5 July 2015 / Revised: 30 July 2015 / Accepted: 6 August 2015 / Published: 13 August 2015
(This article belongs to the Section Organic Synthesis)
Abstract
Eight novel N′-(2-oxoindolin-3-ylidene)-2-propylpentane hydrazide-hydrazone derivatives 4a–h were synthesized and fully characterized by IR, NMR (1H-NMR and 13C-NMR), elemental analysis, and X-ray crystallography. The cyto-toxicity and in vitro anti-cancer evaluation of the prepared compounds have been assessed against two different human tumour cell lines including human liver (HepG2) and leukaemia (Jurkat), as well as in normal cell lines derived from human embryonic kidney (HEK293) using MTT assay. The compounds 3e, 3f, 4a, 4c, and 4e revealed promising anti-cancer activities in tested human tumour cells lines (IC50 values between 3 and 7 μM) as compared to the known anti-cancer drug 5-Fluorouracil (IC50 32–50 μM). Among the tested compounds, 4a showed specificity against leukaemia (Jurkat) cells, with an IC50 value of 3.14 μM, but this compound was inactive in liver cancer and normal cell lines. View Full-TextKeywords:
valproic acid; isatin; hydrazide-hydrazone; anti-cancer activity
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MDPI and ACS Style
El-Faham, A.; Farooq, M.; Khattab, S.N.; Abutaha, N.; Wadaan, M.A.; Ghabbour, H.A.; Fun, H.-K. Synthesis, Characterization, and Anti-Cancer Activity of Some New N′-(2-Oxoindolin-3-ylidene)-2-propylpentane hydrazide-hydrazones Derivatives. Molecules 2015, 20, 14638-14655.
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