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Synthesis of certain tetrahydroacridine derivatives of anticipated medicinal value

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Abstract

This study aims at the synthesis and evaluation of the chemotherapeutic activity of a number of 9-substituted tetrahydroacridine derivatives. The starting material, acridine hydrazide, could be prepared through the interaction between cyclohexanone and anthranilic acid, then chlorination of the product, then condensation of the last compound with hydrazine hydrate. The structures of the new compounds were established by IR, 1H NMR, MS spectra, and elemental analysis in certain cases. Antitumor activities as a trial to obtain more effective and less toxic agents were evaluated. The antitumor activity results indicated that the selected tetrahydroacridine derivatives showed antitumor activity against the liver cancer (HEPG2) tumor cell line tested, but with varying intensities in comparison to the known anticancer drugs, 5-fluorouracil and doxorubicin. It was found that compound VIb was the most active and induced a marked growth inhibition (0.694 μg/ml concentration) in a dose-dependent manner against liver cancer (HEPG2), while compound XVIIIa was second in regards to the growth inhibition activity (2.97 μg/ml concentration).

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Acknowledgments

The authors are grateful to the members of the Therapeutical Chemistry Department, Pharmaceutical and Drug Industries Division, National Research Centre, for helping to accomplish this work.

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Authors and Affiliations

  1. Medicinal Chemistry Department, National Research Centre, Dokki, Cairo, Egypt

    Omar A. Fathhalla & Rehab Sayed Ahmed Ismail

  2. Organic Chemistry Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt

    Mosaad S. Mohamed & Rehab Sayed Ahmed Ismail

  3. Pharmaceutical Chemistry Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt

    Madeha A. Farag & Rehab Sayed Ahmed Ismail

Authors
  1. Omar A. Fathhalla
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  2. Mosaad S. Mohamed
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  3. Madeha A. Farag
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  4. Rehab Sayed Ahmed Ismail
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Correspondence to Omar A. Fathhalla.

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Fathhalla, O.A., Mohamed, M.S., Farag, M.A. et al. Synthesis of certain tetrahydroacridine derivatives of anticipated medicinal value. Res Chem Intermed 39, 3487–3505 (2013). https://doi.org/10.1007/s11164-012-0857-6

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  • DOI: https://doi.org/10.1007/s11164-012-0857-6

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