SYNTHESIS AND IN-VITRO STUDY OF NOVEL (Z)-1-BENZHYDRYL-4-CINNAMYLPIPERAZINE DERIVATIVES AS POTENTIAL ANTICANCER AGENTS

  • S. Shivaprakash BTM II Stage, Bangalore
  • K. R. Kiran BTM II Stage, Bangalore
  • Latha Diwakar BTM II Stage, Bangalore
  • Chandrasekara G Reddy Vittal Mallya Scientific Redearch Foundation

Abstract

Objective: The objective of this study was to synthesize Z- 1-benzhydryl-4-cinnamylpiperazines by novel stereo selective synthetic method and evaluation of their anticancer properties.

Methods: A series of novel (Z)-1-benzhydryl-4-cinnamylpiperazine derivatives (9a-j) were synthesized, starting from benzophenones in six steps. Wittig condensation of appropriate benzyltriphenyl phosphonium halides with various 1-benzhydryl- 4-(2-ethanal) piperazines (3a-j), and column purification over silica gel afforded pure Z- 1-benzhydryl-4-cinnamylpiperazines.

Results: The structures of newly synthesized compounds 9a-j were established by 1H & 13C NMR and mass spectral analysis. The anticancer potential (MTT assay) of synthesized compounds was tested against human cervical cancer (HeLa) and murine microglial (BV-2) cell lines. Results indicated that the most of the Z-derivatives exhibited moderate to good anticancer activity on both the cell lines over their E- antipodes.

Conclusion: Compound 9i (cis- flunarizine) exhibited exceptionally superior activity against both HeLa and BV-2 cell lines with IC50 value of 13.23±3.51 µM and 23.1±4.12 µM respectively. Hence, this compound may be considered to be a potential lead molecule for further development

 

Keywords: Benzophenones, Cinnamylpiperazine derivatives, Wittig reaction, Cinnarizine, Anticancer activity

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Author Biography

Chandrasekara G Reddy, Vittal Mallya Scientific Redearch Foundation
Research Co-ordinator

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Shivaprakash, S., K. R. Kiran, L. Diwakar, and C. G. Reddy. “SYNTHESIS AND IN-VITRO STUDY OF NOVEL (Z)-1-BENZHYDRYL-4-CINNAMYLPIPERAZINE DERIVATIVES AS POTENTIAL ANTICANCER AGENTS”. International Journal of Pharmacy and Pharmaceutical Sciences, Vol. 7, no. 1, Nov. 2014, pp. 416-20, https://innovareacademics.in/journals/index.php/ijpps/article/view/3849.
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