New palladium(II) complexes bearing pyrazole-based Schiff base ligands: Synthesis, characterization and cytotoxicity

Adnan S. Abu-Surrah, Kayed A. Abu Safieh, Iman M. Ahmad, Maher Y. Abdalla, Mikdad T. Ayoub, Abdussalam K. Qaroush, Ahmad M. Abu-Mahtheieh

Research output: Contribution to journalArticle

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Abstract

Reactions of 5-hydrazino-1,3-dimethyl-4-nitro-1H-pyrazole (1) with substituted benzaldehydes (2-5) in methanol gave the new substituted benzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone Schiff base ligands (6-9) benzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone (H-BDH, 6), 2,3-dimethoxybenzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone (MeO-BDH, 7), 4-chlorobenzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone (Cl-BDH, 8), and 4-hydroxybenzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone (OH-BDH, 9) in moderate to excellent yields. Reactions of these pyrazole-based Schiff bases with [PdCl2(NCPh)2] in acetone at room temperature gave the trans-palladium(II) complexes trans-[PdCl2(L)2] (10-13) (L = 6-9). The isolated compounds were characterized by their physical properties, elemental analysis, IR-, MS (EI)- and NMR-spectroscopy. The cytotoxic effect of these complexes against the fast growing head and neck squamous carcinoma cells SQ20B and SCC-25 has been studied. The influence was dose dependent and varies by cell type. The complexes 11, 12, and 13 had higher clonogenic cytotoxic effect than cisplatin when tested on SQ20B cell line.

Original languageEnglish (US)
Pages (from-to)471-475
Number of pages5
JournalEuropean Journal of Medicinal Chemistry
Volume45
Issue number2
DOIs
StatePublished - Feb 1 2010

Fingerprint

Bearings (structural)
Hydrazones
Schiff Bases
Palladium
Cytotoxicity
Ligands
Benzaldehydes
Acetone
Cisplatin
Nuclear magnetic resonance spectroscopy
Methanol
Magnetic Resonance Spectroscopy
Physical properties
Cells
pyrazole
Cell Line
Temperature
Chemical analysis

Keywords

  • Head and neck carcinoma
  • N-methylpyrazole
  • Palladium(II) complexes
  • Schiff bases

ASJC Scopus subject areas

  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

Cite this

New palladium(II) complexes bearing pyrazole-based Schiff base ligands : Synthesis, characterization and cytotoxicity. / Abu-Surrah, Adnan S.; Abu Safieh, Kayed A.; Ahmad, Iman M.; Abdalla, Maher Y.; Ayoub, Mikdad T.; Qaroush, Abdussalam K.; Abu-Mahtheieh, Ahmad M.

In: European Journal of Medicinal Chemistry, Vol. 45, No. 2, 01.02.2010, p. 471-475.

Research output: Contribution to journalArticle

Abu-Surrah, Adnan S. ; Abu Safieh, Kayed A. ; Ahmad, Iman M. ; Abdalla, Maher Y. ; Ayoub, Mikdad T. ; Qaroush, Abdussalam K. ; Abu-Mahtheieh, Ahmad M. / New palladium(II) complexes bearing pyrazole-based Schiff base ligands : Synthesis, characterization and cytotoxicity. In: European Journal of Medicinal Chemistry. 2010 ; Vol. 45, No. 2. pp. 471-475.
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abstract = "Reactions of 5-hydrazino-1,3-dimethyl-4-nitro-1H-pyrazole (1) with substituted benzaldehydes (2-5) in methanol gave the new substituted benzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone Schiff base ligands (6-9) benzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone (H-BDH, 6), 2,3-dimethoxybenzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone (MeO-BDH, 7), 4-chlorobenzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone (Cl-BDH, 8), and 4-hydroxybenzaldehyde (1,3-dimethyl-4-nitro-1H-pyrazol-5-yl)hydrazone (OH-BDH, 9) in moderate to excellent yields. Reactions of these pyrazole-based Schiff bases with [PdCl2(NCPh)2] in acetone at room temperature gave the trans-palladium(II) complexes trans-[PdCl2(L)2] (10-13) (L = 6-9). The isolated compounds were characterized by their physical properties, elemental analysis, IR-, MS (EI)- and NMR-spectroscopy. The cytotoxic effect of these complexes against the fast growing head and neck squamous carcinoma cells SQ20B and SCC-25 has been studied. The influence was dose dependent and varies by cell type. The complexes 11, 12, and 13 had higher clonogenic cytotoxic effect than cisplatin when tested on SQ20B cell line.",
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AU - Abu Safieh, Kayed A.

AU - Ahmad, Iman M.

AU - Abdalla, Maher Y.

AU - Ayoub, Mikdad T.

AU - Qaroush, Abdussalam K.

AU - Abu-Mahtheieh, Ahmad M.

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