Synthesis of Dihydrocoumarin derivatives from Methyl trans-Cinnamate And Evaluation of their Bioactivity as Potent anticancer Agents
Keywords:
dihydrocoumarin derivatives, methyl trans-cinnmate, cinnamic acid, 4-phenylchroman-2-one, 8-methyl -4- phenylchroman-2-one, and 6-methyl-4-phenylchroman-2-oneAbstract
Synthesis of dihydrocoumarin derivatives from methyl trans-cinnamate is described. The reaction can be carried out as a simple one pot reaction using acid catalyst. Firstly, methyl trans-cinnamate was converted into cinnamic acid via hydrolysis reaction with alkaline. Secondly, esterification reaction of cinnamic acid was carried out by using an acid catalyst p-toluensulfonic acid with phenol, o-cresol, p-cresol which lead to the production of 4-phenylchroman-2-one, 8-methyl -4-phenylchroman-2-one, and 6-methyl-4-phenylchroman-2-one.
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References
Sinaga, Erna. Alpinia galanga (L.) Willd., Lengkuas. Pusat Penelitian dan Pengembangan Tumbuhan Obat UNAS (P3TO UNAS). http://www.warintek.ristek.go.id/pangan_kesehatan/tanaman_obat /depkes/Bunglai % 20laki.pdf, tanggal 10 Mei 2012.
Ernawati, Teni, Deana Wahyuningrum, Minarti, Yulia Anita, Lia Meilawati, dan Puspa D. Lotulung, “Development of Raw Materials for Drugs by Using Methyl trans Cinnamate Isolated from Galangal (Alpinia malaccensis) as Novel Approaches to Drug Discoveryâ€. In Proceeding of The Eijkman Institute Comes of Age: Vitamins, Genomics, dan Welfar. Jakarta: Eijkman Institute for Molecular Biology, PIV-5, pp 146, 2011.
Muchtaridi, Ikhsan Rambia, Ida Musfiroh. Kadar Metil Sinamat dari Batang, Daun dan Rimpang Tumbuhan Laja Gowah (Alpinia Malaccensis (Burm f.)) dengan GC/MS. Fakultas Farmasi Universitas Padjajaran, 2008.
Li, Q. F., S. L. Shi, Q. R. Liu, J. Tang, J. Song, dan Y. Liang. “ Anticancer Effects of Ginsenoside Rg1, Cinnamic Acid, and Tanshinone in Osteosarcoma MG-63 Cells: Down Regulation and Cytoplasmic Trafficking of Neucleophosminâ€, Int. J. Biochem. Cell Biol, Vol. 40,pp.1918 – 1929, 2008.
Baltas,M. P. De, dan F. Bedos Belval. “Cinnamis Acid Derivatives as Anticancer Agents- A Review. Current Medicinal Chemistryâ€, Vol.18, pp.1672 – 1703, 2011.
Bairwa, Ranjeet, Mariam S. Degani, “Novel Molecular Hybrid of Cinnamic Acids and Guanylhidrazones as Potential Antitubercular Agentsâ€, Bioorganic and Medicinal Chemistry Letters, Vol.20, pp.1623 – 1625, 2010.
Li, Kelin, Lindsay N. Foressee, dan Jon A. Tunge. “Trifluoroacetic Acid Mediated Hydroarylation: Synthesis of Dihydrocoumarins dan Dihydroquinolonesâ€, J. Org. Chem, Vol.70 (7), pp. 2881 – 2883, 2005.
Lin, Hsiu Chen, Shin Hui Tsai, Chien Shu Chen, “Structure Activity Relationship of Coumarin Derivatives on Xanthine oxidase Inhibiting and Free Radical-Scavenging Activitiesâ€, Biochemical Pharmacology, Vol.75, pp.1416 – 1425, 2008.
Baba, Masaki, Yongri Jin, Atsuo Mizuno, Studies on Cancer Chemoprevention by Traditional Folk Medicines XXIV, “Inhibitory Effect of A Coumarin Derivative, 7-isopentenylcoumarin, Against Tumor-Preventionâ€, Biol. Pharm. Bull, Vol. 25 (2), pp. 244 – 246, 2002.
Ekowati, Heny, Indwiani Astuti, dan Mustofa, “Anticancer Activity of Calanone on HeLa Cell Lineâ€, Indo. J. Chem, Vol.10(2), pp. 247 – 251, 2010.
Chuang, Jing-Yuang, Yung Feng Huang, Hsu Feng Lu, “Coumarin Induces Cell Cycle Arrest and Apoptosis in Human Cervical Cancer HeLa Cells Through A Mitochondria and Caspase-3 Dependent Mechanism and NF-kB Down-Regulationâ€, In vivo, Vol. 2t, pp.1003 – 1010, 2007.
Sudalai, A. dan A. R. Jagdale. “p-toluenesulfonic acid Mediated Hydroarilation of Cinnamic Acids with Anisoles and Phenols Under Metal and Solvent-Free Conditionsâ€, Tetrahedron Letters, Vol. 48, pp. 4895 – 4898, 2007.
Dey, P. M. dan J. B. Harborne, “Methods in Plant Biochemistry: Assays for Bioactivityâ€, Volume 6. London: Academic Press, pp. 1 – 30, 1991.
McLaughlin, Jerry L., Lingling L. Rogers, dan Jon E. Anderson, “The Use of Biological Assays to Evaluate Botanicalsâ€, Drug Information Journal, Vol.32, pp. 513 – 524, 1998.
Wu, Bin, Jin-Shui Zhu, Yi Zhang, Wei-Ming Shen, dan Qiang Zhang, “ Predictive Value of MTT Assay as An in vitro Chemosensitivity Testing for Gastric Cancer: One Institution’s Experienceâ€, World Journal Gastroenterology, Vol.14 (19), pp. 3064 – 3068, 2008.
Sumaryono, Wahono dan Agung Eru Wibowo, “Aktivitas sitotoksik Ekstrak Etanol Daun Aglaia elliptica Blume terhadap Galur Sel Kanker Serviks (HeLa)â€, J. Ilmu Kefarmasian Indonesia, Vol. 8(1), pp. 19 – 23, 2010.
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