Novel 1-((benzoimidazole-2-yl)methyl)-3-phenyl- 1,4-dihydropyrazole-5-one and their derivatives

Synthesis and preliminary cytotoxicity test as anti-breast cancer

Mariam Abubaker, Che Wan Zanariah Che Wan Ngah, Musa Ahmad, Bambang Kuswandi

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

This work presented synthesis of new pyrazolone derivatives and their cytotoxicity assay. The synthesis of pyrazolone derivatives have been achieved using condensation of 2-hydrazinyl methyl-1H-benzoimidazole (H1) with ethylbenzoylacetate in presence of ethanol, which in turn, yielded 1-(benzoimidazole-2-yl)methyl-3-phenyl-1, 4-dihydropyrazole-5-one (BPP). Then, it has reacted with diazonium solution in ethanol and benzoyl chloride in hot dioxin to give 4-azo pyrazolone (BMPAP) and 4-acyl pyrazolone (BMPBP) respectively. The newly synthesized compounds were characterized by FT-IR, 1H NMR and13C NMR. The cytotoxicity assay of the BPP, BMPAP and BMPBP on human breast cancer cells (MCF7) demonstrated their killing ability similar with naturally occurring toxins or immune-mediator cells. The cytotoxicity test was performed using MTT assay (3-[4, 5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide). Cell culture with the concentration of 2×104 cells/ml was prepared and was plated (100 µl/well) onto 96-well plates. The diluted ranges of sample extracts were added to each well with identified concentrations: 100, 50, 25, 12.5, 6.25, 3.13 and 1.56 µg/ml and then incubated for 72 hr. MTT solution was added at the end of incubation samples to the cells and continued further for incubation in 3 hr. After solubilization of the purple formazan crystals using DMSO were completed, the Optical Density (OD) was measured using an ELISA reader at a wavelength of 570 nm. The cytotoxicity was recorded as the drug concentration causing 50% growth inhibition of the tumor cells (IC50 value). Overall cytotoxicity test was varied between pyrazolone derivatives with 50% or higher inhibition below 27 µg/ml, and it was considered active and potentially target for further screening.

Original languageEnglish
Pages (from-to)4532-4536
Number of pages5
JournalAdvanced Science Letters
Volume23
Issue number5
DOIs
Publication statusPublished - 1 May 2017
Externally publishedYes

Fingerprint

Cytotoxicity
Breast Cancer
cancer
Synthesis
Breast Neoplasms
Derivatives
Derivative
Cell
Multi-target Tracking
Assays
Cells
Ethanol
assay
nuclear magnetic resonance
ethanol
drug
incubation
Nuclear magnetic resonance
Formazans
ability

Keywords

  • Anti-breast cancer
  • Cytotoxicity assay
  • Pyrazolone derivatives
  • Synthesis
  • Tumor cells

ASJC Scopus subject areas

  • Health(social science)
  • Computer Science(all)
  • Education
  • Mathematics(all)
  • Environmental Science(all)
  • Engineering(all)
  • Energy(all)

Cite this

Novel 1-((benzoimidazole-2-yl)methyl)-3-phenyl- 1,4-dihydropyrazole-5-one and their derivatives : Synthesis and preliminary cytotoxicity test as anti-breast cancer. / Abubaker, Mariam; Ngah, Che Wan Zanariah Che Wan; Ahmad, Musa; Kuswandi, Bambang.

In: Advanced Science Letters, Vol. 23, No. 5, 01.05.2017, p. 4532-4536.

Research output: Contribution to journalArticle

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AB - This work presented synthesis of new pyrazolone derivatives and their cytotoxicity assay. The synthesis of pyrazolone derivatives have been achieved using condensation of 2-hydrazinyl methyl-1H-benzoimidazole (H1) with ethylbenzoylacetate in presence of ethanol, which in turn, yielded 1-(benzoimidazole-2-yl)methyl-3-phenyl-1, 4-dihydropyrazole-5-one (BPP). Then, it has reacted with diazonium solution in ethanol and benzoyl chloride in hot dioxin to give 4-azo pyrazolone (BMPAP) and 4-acyl pyrazolone (BMPBP) respectively. The newly synthesized compounds were characterized by FT-IR, 1H NMR and13C NMR. The cytotoxicity assay of the BPP, BMPAP and BMPBP on human breast cancer cells (MCF7) demonstrated their killing ability similar with naturally occurring toxins or immune-mediator cells. The cytotoxicity test was performed using MTT assay (3-[4, 5-dimethylthiazol-2-yl]-2,5-diphenyltetrazolium bromide). Cell culture with the concentration of 2×104 cells/ml was prepared and was plated (100 µl/well) onto 96-well plates. The diluted ranges of sample extracts were added to each well with identified concentrations: 100, 50, 25, 12.5, 6.25, 3.13 and 1.56 µg/ml and then incubated for 72 hr. MTT solution was added at the end of incubation samples to the cells and continued further for incubation in 3 hr. After solubilization of the purple formazan crystals using DMSO were completed, the Optical Density (OD) was measured using an ELISA reader at a wavelength of 570 nm. The cytotoxicity was recorded as the drug concentration causing 50% growth inhibition of the tumor cells (IC50 value). Overall cytotoxicity test was varied between pyrazolone derivatives with 50% or higher inhibition below 27 µg/ml, and it was considered active and potentially target for further screening.

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