Publication: One-pot three steps cascade synthesis of novel isoandrographolide analogues and their cytotoxic activity
Issued Date
2017-01-01
Resource Type
ISSN
17683254
02235234
02235234
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2-s2.0-85025593151
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Mahidol University
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SCOPUS
Bibliographic Citation
European Journal of Medicinal Chemistry. Vol.138, (2017), 952-963
Suggested Citation
Teerapich Kasemsuk, Pawinee Piyachaturawat, Rada Bunthawong, Uthaiwan Sirion, Kanoknetr Suksen, Apichart Suksamrarn, Rungnapha Saeeng One-pot three steps cascade synthesis of novel isoandrographolide analogues and their cytotoxic activity. European Journal of Medicinal Chemistry. Vol.138, (2017), 952-963. doi:10.1016/j.ejmech.2017.07.035 Retrieved from: https://repository.li.mahidol.ac.th/handle/20.500.14594/42220
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Title
One-pot three steps cascade synthesis of novel isoandrographolide analogues and their cytotoxic activity
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Abstract
© 2017 Elsevier Masson SAS An efficient one-pot synthesis of novel andrographolide analogues is reported from a naturally occurring and abundant andrographolide isolated from aerial parts of Andrographis paniculata. Reactions in the one-pot proceed through a cascade epoxide ring opening by aniline derivatives/intramolecular ring closing and oxa-conjugate addition-elimination reactions. This methodology produces a new series of 17-amino-8-epi-isoandrographolide analogues in fair to excellent yields with high stereoselectivity using an economic and environmental procedure without base or catalyst at room temperature. Twenty-five analogues were obtained and cytotoxicity of all new analogues were evaluated against six cancer cell lines to search for a new lead compound based on andrographolide structure.
