Publication: Synthesis and cytotoxic activity of new 7-acetoxy-12-amino-14-deoxy andrographolide analogues
Issued Date
2021-02-01
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ISSN
14643405
0960894X
0960894X
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2-s2.0-85098674820
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Mahidol University
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SCOPUS
Bibliographic Citation
Bioorganic and Medicinal Chemistry Letters. Vol.33, (2021)
Suggested Citation
Rada Bunthawong, Uthaiwan Sirion, Arthit Chairoungdua, Kanoknetr Suksen, Pawinee Piyachaturawat, Apichart Suksamrarn, Rungnapha Saeeng Synthesis and cytotoxic activity of new 7-acetoxy-12-amino-14-deoxy andrographolide analogues. Bioorganic and Medicinal Chemistry Letters. Vol.33, (2021). doi:10.1016/j.bmcl.2020.127741 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/76295
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Title
Synthesis and cytotoxic activity of new 7-acetoxy-12-amino-14-deoxy andrographolide analogues
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Abstract
Two new series of 19-silylether- and 19-formyl-7-acetyl-12-amino-14-deoxyandrographolide analogues were designed and synthesized from natural andrographolide via key step reactions including allylic hydroxylation, tandem CAE reaction and one pot formylation. Evaluation of their cytotoxicity against eight cancer cells line found 6e exhibited the highest activity on MCF-7 cancer cell (IC50 2.93) and comparable to the drug elipticin. Replacement of silylether at C-19 with formyl group exhibited selective activity on P-388 cell line. Computational studies revealed the amino group at C-12 and O-acetoxy at C-7 position play significant roles in cytotoxicity against MCF-7 cancer cells. Cytotoxicity of these two series highlights the importance of 12-substituted-14-deoxyandrographolide scaffold and these types of compounds could be employed in future developments against breast cancer.