β-Elemene derivatives produced from SeO ₂ -mediated oxidation reaction

Abstract

Herein, we report the first access of β-elemene derivatives through the SeO 2 -mediated oxidation reaction. Several new compounds were isolated through such a one-step reaction, and their structures were elucidated using various 2D-NMR techniques. This method provides easy access to multiple oxidative β-elemene derivatives in one single step and represents the first modifications on cyclohexyl ring of β-elemene. It is expected to open up the opportunity for future derivatization on cyclohexyl ring of β-elemene. The new compounds obtained above showed better anti-proliferation activities than β-elemene itself on several cancer cell lines. Among them, compound 17 shows the best activity in antiproliferation assays of A549 and U-87MG cell lines.

Design, synthesis and biological evaluation of novel histone deacetylase (HDAC) inhibitors derived from β -elemene scaffold

“…It was discovered by us that the two allylic chloro groups had differentiated reactivity in the presence of a nucleophile. This is presumably due to the stereo effects in the chair-like conformation of cyclohexane ring, in which slightly more bulky around 14-position in 21 leads to less reactivity than 13-position 46 . By carefully controlling the reaction conditions, two different R 3 were installed at position 13- of 21 to yield intermediate 22 .…”

Nickel-catalyzed cross-electrophile allylation of vinyl bromides and the modification of anti-tumour natural medicine β-elemene

“…β-Elemene is an anti-tumour natural medicine, which is a sesquiterpene exacted from the rhizome of Traditional Chinese Medicine (TCM) Curcuma wenyujin . 21 After years of experimentation and efforts, 22 elemene oral emulsion (CFDA number H20010338) and elemene injection (CFDA number H10960114) developed by our research team were approved by the China Food and Drug Administration (CFDA) as broad-spectrum anti-tumour drugs in the 1990s ( Fig. 3a ).…”

Functionalized Chromans from ortho-Quinone Methides and Arylallenes

“…It should be noted that while both C2 and C4 positions are benzylic as well as allylic in nature, the fact that C2 is adjacent to the pyran oxygen may provide a handle to distinguish these two positions during the functionalization. In deed, upon treating with SeO 2 , depending on the nature of the group at C4 as well as the reaction temperature, these 3-methylenechromans underwent the Riley oxidation to afford the corresponding 3-acyl-2 H -chromenes 23a – 23f , the chromenols 24a – 24d and/or the 3-formyl-2-arylchromenes 25a – 25f . It is apparent that both allylic positions at C2 and C4 could undergo the Riley oxidation to furnish different types of products as delineated in Scheme .…”