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Synthesis of new phosphate derivative of benzothiazole and its inhibiting effect on two series of human neuroblastoma cell growth

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Abstract

The sodium salt of di ((1-hydroxy-2-benzothiazolium-1-yl) ethyliden-1,1-H-bisphosphonic acid) orthophosphate was synthesized and its toxicity and viability effects screened on two different human neuroblastoma cell lines. This novel derivative of benzothiazole provides a new compound in connection with research and therapeutic application for tumor cell growth inhibition. Benzothiazole was alkylated in reaction with bromoacetic acid and then converted to its H-bisphosphonic acid derivative in presence of H3PO3/POCl3. The procedure led to formation of two molecules of corresponding H-bisphosphonic acid which attached together via a phosphate bridge. The investigated compound exhibits activities (IC50 value) ranging from 14–23 μM (corresponding to human neuroblastoma SK-BE (2) and SK-NM-C cells).

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Authors and Affiliations

  1. Department of Chemistry, Islamic Azad University, Central Tehran Branch, Tehran, Iran

    Mahshid Nikpour Nezhati, Homayon Ahmad Panahi, Mohammad Mehdi Sadughi & Reihaneh Kooshkestani

  2. Department of Pharmacology, Tehran University, Tehran, Iran

    Gholam Hossein Riazi

  3. Department of Chemistry, Islamic Azad University, Varamin Branch (Pishva), Iran

    Elham Moniri

  4. Department of Chemistry, Imam Khomeini International University (IKIU), Qazvine, Iran

    Nasir Ahmad Rajabi

  5. Young Researchers Club, Islamic Azad University, Central Tehran Branch, Tehran, Iran

    Nasir Ahmad Rajabi

  6. Young Researchers Club, Islamic Azad University, Ghaemshahr Branch, Tehran, Iran

    Mohammad Mehdi Sadughi

  7. Department of Microbiology, Islamic Azad University, Science and Research Campus, Tehran, Iran

    Natasha Rahmani Zaker

  8. Department of Biochemistry, Alzahra University, Tehran, Iran

    Robab Ardekani

Authors
  1. Mahshid Nikpour Nezhati
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  2. Gholam Hossein Riazi
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  3. Homayon Ahmad Panahi
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  4. Elham Moniri
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  5. Nasir Ahmad Rajabi
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  6. Mohammad Mehdi Sadughi
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  7. Natasha Rahmani Zaker
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  8. Robab Ardekani
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  9. Reihaneh Kooshkestani
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Correspondence to Mahshid Nikpour Nezhati.

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Nezhati, M.N., Riazi, G.H., Panahi, H.A. et al. Synthesis of new phosphate derivative of benzothiazole and its inhibiting effect on two series of human neuroblastoma cell growth. Korean J. Chem. Eng. 30, 675–679 (2013). https://doi.org/10.1007/s11814-012-0191-0

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  • DOI: https://doi.org/10.1007/s11814-012-0191-0

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