Synthesis and Evaluation of Anticancer Activity of O-allylchalcone Derivatives

A large number of novel O -allylchalcones were synthesized by Claisen Schmidt condensation reaction of O -allylvanillin 3 with appropriate substituted acetophenones 4a-h. These model chalcones 5a-h and their precursor O -allylvanillin were screened for their in vitro cytotoxicactivity against four human cancer cell lines. The most potent compound in this series with the IC 50 values below or around 10 μM were 5f against THP-1 cells (10.42 μM) and 5g against THP-1 (4.76 μM), DU-145 (5.21 μM), HL60 (7.90 μM), Hep-G2 (10.12 μM) and MCF-7 (10.32 μM).

[1]  G. Zarrini,et al.  Synthesis, in vitro antimicrobial and antioxidant activities of chalcone and flavone derivatives holding allylic substitutions , 2011, Medicinal Chemistry Research.

[2]  T. Efferth,et al.  Cytotoxicity and mode of action of four naturally occuring flavonoids from the genus Dorstenia: gancaonin Q, 4-hydroxylonchocarpin, 6-prenylapigenin, and 6,8-diprenyleriodictyol. , 2011, Planta medica.

[3]  N. Suh,et al.  Synthesis and biological evaluation of retinoid-chalcones as inhibitors of colon cancer cell growth. , 2010, Bioorganic & medicinal chemistry letters.

[4]  M. Ninova,et al.  Examination of growth inhibitory properties of synthetic chalcones for which antibacterial activity was predicted. , 2009, European journal of medicinal chemistry.

[5]  B. Annabi,et al.  Inhibition of matrix metalloproteinase-2 secretion by chalcones from the twigs of Dorstenia barteri Bureau , 2006 .

[6]  N. Davidson,et al.  Anticancer activities of novel chalcone and bis-chalcone derivatives. , 2006, Bioorganic & medicinal chemistry.

[7]  Sarot Cheenpracha,et al.  Anti-HIV-1 protease activity of compounds from Boesenbergia pandurata. , 2006, Bioorganic & medicinal chemistry.

[8]  A. Kharazmi,et al.  Conformationally restricted anti-plasmodial chalcones. , 2005, Bioorganic & medicinal chemistry letters.

[9]  A. Amaral,et al.  Brazilian phytopharmaceuticals – evaluation against hospital bacteria , 2005, Phytotherapy research : PTR.

[10]  K. Jenett-Siems,et al.  In vitro antiplasmodial activity of prenylated chalcone derivatives of hops (Humulus lupulus) and their interaction with haemin. , 2005, The Journal of antimicrobial chemotherapy.

[11]  N. Lawrence,et al.  The chemistry and biology of antimitotic chalcones and related enone systems. , 2005, Current pharmaceutical design.

[12]  R. Yunes,et al.  Antifungal Activity and Studies on Mode of Action of Novel Xanthoxyline‐Derived Chalcones , 2005, Archiv der Pharmazie.

[13]  X. Wu,et al.  Chalcones: an update on cytotoxic and chemoprotective properties. , 2005, Current medicinal chemistry.

[14]  K. Lee,et al.  Anti-AIDS agents 54. A potent anti-HIV chalcone and flavonoids from genus Desmos. , 2003, Bioorganic & medicinal chemistry letters.

[15]  M. Payá,et al.  ttCH, a selective inhibitor of inducible nitric oxide synthase expression with antiarthritic properties. , 2003, European journal of pharmacology.

[16]  P. Trouillas,et al.  Chalcones: structural requirements for antioxidant, estrogenic and antiproliferative activities. , 2001, Anticancer research.

[17]  C. Olsen,et al.  Synthetic and biological activity evaluation studies on novel 1,3-diarylpropenones. , 2001, Bioorganic & medicinal chemistry.

[18]  A. Izzo,et al.  Flavonoids: old and new aspects of a class of natural therapeutic drugs. , 1999, Life sciences.

[19]  E. Park,et al.  Licochalcone A: An Inducer of Cell Differentiation and Cytotoxic Agent from Pogostemon cabling 1 , 1998, Planta medica.

[20]  D. Scudiero,et al.  New colorimetric cytotoxicity assay for anticancer-drug screening. , 1990, Journal of the National Cancer Institute.

[21]  H. Depypere,et al.  A safety study of oral tangeretin and xanthohumol administration to laboratory mice. , 2005, In vivo.

[22]  M. Alcaraz,et al.  4-dimethylamino-3',4'-dimethoxychalcone downregulates iNOS expression and exerts anti-inflammatory effects. , 2001, Free radical biology & medicine.