Synthesis of a novel series of artemisinin dimers with potent anticancer activity involving Sonogashira cross-coupling reaction

Stereoselective chlorothiolation of artemisinin-derived C-10 oxa terminal alkynes

“…Accordingly, artemisinin is treated with NaBH 4 in MeOH at 0 • C to afford dihydroartemisinin 2 in 90 % yield which upon treatment with propargyl/homopropargyl alcohol in the presence of BF 3 ·OEt 2 in dichloromethane afforded artemisinin-derived terminal alkynes 5a/5b [6][7][8][9][10][11]. Initially, we attempted the chlorothiolation reaction on 5a in dichloroethane using 4-methylbenzenesulfenylchloride which was generated in situ from the reaction of 4-methylbenzenthiol with N-chlorosuccinamide [28].…”

“…Moreover, Haynes et al reported artemisone as one of the sulfur-containing second-generation derivatives of artemisinin which is now undergoing clinical trials [12]. Inspired by the potent anticancer sulfur-containing artemisinin derivatives, and in continuation of our interest in maximizing the structural diversity of artemisinin analogs to find potent anticancer agents, we wish to report the stereoselective chlorothiolation of artemisinin-derived C-10 oxa alkynes [6][7][8][9][10][11].…”

“…2). Efforts in this direction have yielded a large number of artemisinin analogs with profound anticancer or antimalarial activities, and are in different stages of clinical development [6][7][8][9][10][11][12]26].…”

Synthesis of a novel series of fluoroarene derivatives of artemisinin as potent antifungal and anticancer agent

“…Although host immunity plays a role in the occurrence Fusarium infections in human. As part of our continuing search for new and more structurally diverse artemisinin analogues, [17][18][19][20][21][22][23][24] we herein report on the in vitro antifungal activity of a series of artemisinin derivatives against this organism. A series of nine flouro arene derivaties of artemisinin are prepared for this study.…”

“…In our previous studies we have reported the anticancer activities of various artemisinin derivatives. [17][18][19] Very recently, we have reported application of Sonogashira cross-coupling in the synthesis of artemisinin dimer derivatives. 17 In this paper we will report application of palladium catalysed Suzuki cross-coupling reaction to get these novel derivatives.…”