One-pot three steps cascade synthesis of novel isoandrographolide analogues and their cytotoxic activity

Eur J Med Chem. 2017 Sep 29:138:952-963. doi: 10.1016/j.ejmech.2017.07.035.

Teerapich Kasemsuk ¹, Pawinee Piyachaturawat ², Rada Bunthawong ³, Uthaiwan Sirion ³, Kanoknetr Suksen ², Apichart Suksamrarn ⁴, Rungnapha Saeeng ⁵

Affiliations

1 Department of Chemistry, Faculty of Science and Technology, Rambhai Barni Rajabhat University, Chanthaburi, 22000, Thailand.
2 Department of Physiology, Faculty of Science, Mahidol University, Bangkok, 10400, Thailand.
3 Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi, 20131, Thailand.
4 Department of Chemistry, Faculty of Science, Ramkhamhaeng University, Bangkok, 10240, Thailand.
5 Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi, 20131, Thailand. Electronic address: rungnaph@buu.ac.th.

PMID: 28755636 DOI: 10.1016/j.ejmech.2017.07.035

Abstract

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.

Keywords

Andrographis paniculata; Cytotoxic activity; Epiandrographolide.

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