Journal of Applied Biological Chemistry

The Korean Society for Applied Biological Chemistry (한국응용생명화학회)
권호 표지
DOI QR코드

DOI QR Code

Synthesis and Identification of Novel Pyrazoline and Its Anti-cancer Property

새로운 피라졸린 화합물의 합성과 구조결정 및 항암효과

  • Koh, Dong-Soo (Department of Applied Chemistry, Dongduk Women's University)
  • 고동수 (동덕여자대학교 응용화학과)
  • Received : 2011.05.31
  • Accepted : 2011.06.04
  • Published : 2011.06.30
Download PDF
⟨ Previous Next ⟩

Abstract

Novel pyrazoline (4) was synthesized from chalcone (3) which was prepared from 2'-hydroxy-l'acetonaphthone (1) and 4-methoxy benzaldehyde (2). Pyrazoline (4) forms resonance assisted hydrogen bond between naphthol hydroxyl group and imine nitrogen in a pyrazoline ring. Pyrazoline (4) shows Poly ADP-ribose Polymerase (PARP) cleavage ability as a proof of apoptosis in cancer cell, which reveals its anti-cancer property.

Keywords

References

  1. Chin J, Kim DC, Kim HJ, Panosyan FB, and Kim KM (2004) Chiral shift reagent for amino acids based on resonance-assisted hydrogen bonding. Org Lett 6, 2591-2593. https://doi.org/10.1021/ol049084x
  2. Congiu C, Onnis V, Vesci L, Castronia M, and Pisano C (2010) Synthesis and in vitro antitumor activity of new 4,5-dihydroxypyrazol derivatives. Bioorg Med Chem 18, 6238-6248. https://doi.org/10.1016/j.bmc.2010.07.037
  3. Dittmer C, Raabe G, and Hintermann L (2007) Asymmetric cyclization of 2'-hydroxychaicones to flavanones: Catalysis by chiral Bronsted acids and bases. Eur J Org Chem 5886-5898.
  4. Havrylyuk D, Zimenkovsky B, Vasylenko O, Zaprutko L, Gzella A, and Lesyk R (2009) synthesis of novel thiazolone-based compounds containing pyrazolone moiety and evalution of their anti-cancer activity. Eur J Med Chem 44, 114-119.
  5. Joshi RS, Mandhane PG, Diwakar SD, Dabhade SK, and Gill GH (2010) Synthesis, analgesic and anti-inflammatory activities of some novel pyrazoline derivatives. Bioorg Med Chem Lett 20, 3721-3725. https://doi.org/10.1016/j.bmcl.2010.04.082
  6. Kaplancikli ZA, Ozdemir A, Turan-Zitouni G, Altintop MD, and Can OD (2010) New pyrazoline derivatives and their antidepressant activity. Eur J Med Chem 45, 4383-4387. https://doi.org/10.1016/j.ejmech.2010.06.011
  7. Karuppasamy M, Mahapatra M, Yabanoglu S, Ucar G Sinha BA, Basu A, Mishra N, Sharon A, Kulandaivelu U, and Jayaprakash V (2010) Development of selective and reversible pyrazoline based MAO-A inhibitors: Synthesis, biological evaluatim, and docking studies. Bioorg Med Chem 18, 1875-1881. https://doi.org/10.1016/j.bmc.2010.01.043
  8. Koh D (2005) Application of multcomponent reactions in synthesis of diimines as salen analogue. Agric Chem Biotechnol 48, 105-107.
  9. Lazebnik YA, Kaufmann SH, Desnoyers S, Poirier GG, and Earnshow WC (1994) Cleavage of poly(ADP-ribose)polymerase by a proteinase with properities like ICE. Nature 371, 346-347. https://doi.org/10.1038/371346a0
  10. Manna K and Agrawal YK (2009) Microwave assited synthesis of new indophenazine 1,3,5-trisubstituted pyrazoline derivatives of benzofuran and their antimicrobial activity. Bioorg Med Chem Lett 19, 2688-2692. https://doi.org/10.1016/j.bmcl.2009.03.161
  11. Marathey MG (1954) Synthesis of dihydroflavonols and flavonols. J Org Chem 20, 563-571.
  12. Mishra N and Sasmal D (2011) Development of selective and reversible pyrozoline based MAO-B inbibitor: Virtual screening, synthesis and biological evaluation. Bioorg Med Chem Lett 21, 1969-1973. https://doi.org/10.1016/j.bmcl.2011.02.030
  13. Nagata S (2000) Apoptotic DNA fragmentation. Exp Cell Res 256, 12-18. https://doi.org/10.1006/excr.2000.4834
  14. Prasad YR, Rao AL, Prasoona L, Mutali K, and Kumar PR (2005) Synthesis and antidepressant activity of some 1,3,5-triphenyl-2-pyrazolines and 3-(2''-hydroxynaphthalene-1''-yl)-1,5-diphenyl-2-pyrazolines. Bioorg Med Chem Lett 15, 5030-5034. https://doi.org/10.1016/j.bmcl.2005.08.040
  15. Shaharyar M Abdullah MM, Bakht MA, and Majeed J (2010) Pyrazoline bearing benzimidazoles: Search for anticancer agent. Eur J Med Chem 45, 114-119. https://doi.org/10.1016/j.ejmech.2009.09.032
  16. Siddiqui ZN, Musthafa TNM, Ahmad A, and Khan AU (2011) Thermal solvent-free synthesis of novel pyrazolyl chalcones and pyrazolines as potential antimicrobial agents. Bioorg Med Chem Lett 21, 2860-2865. https://doi.org/10.1016/j.bmcl.2011.03.080

Cited by

  1. Complete assignments of 1H and 13C NMR data for 21 naphthalenyl‐phenyl‐pyrazoline derivatives vol.51, pp.9, 2011, https://doi.org/10.1002/mrc.3981