title: 12-Amino-andrographolide analogues: synthesis and cytotoxic activity.
abstract: Andrographolide, a diterpenoid lactone of the plant Andrographis paniculata, has been shown to be cytotoxic against various cancer cells in vitro. In the present study, a series of β-amino-γ-butyrolactone analogues has been synthesized from naturally occurring andrographolide via one pot tandem aza-conjugate addition-elimination reaction. By using economic procedure without any base or catalyst at room temperature, the products obtained were in fair to excellent yields with high stereoselectivity. The cytotoxicity of all new amino analogues were evaluated against six cancer cell lines and revealed their potential for being developed as promising anti-cancer agents.
authors.affiliation: Department of Chemistry and Center for Innovation in Chemistry, Faculty of Science, Burapha University, Chonburi, 20131, Thailand.
authors.forename: Sakkasem
authors.initials: S
authors.lastname: Kasemsuk
authors.forename: Uthaiwan
authors.initials: U
authors.lastname: Sirion
authors.forename: Kanoknetr
authors.initials: K
authors.lastname: Suksen
authors.forename: Pawinee
authors.initials: P
authors.lastname: Piyachaturawat
authors.forename: Apichart
authors.initials: A
authors.lastname: Suksamrarn
authors.forename: Rungnapha
authors.initials: R
authors.lastname: Saeeng
mesh_terms: D035685:Andrographis; D000818:Animals; D000970:Antineoplastic Agents / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D045744:Cell Line, Tumor; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D004224:Diterpenes / Q000138:chemical synthesis* / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor / Q000379:methods; D006801:Humans; D061986:MCF-7 Cells; D051379:Mice; D035261:Plant Components, Aerial; D051381:Rats; D013329:Structure-Activity Relationship
chemical_list: D000970:Antineoplastic Agents; D003603:Cytotoxins; D004224:Diterpenes; C030419:andrographolide