Recent synthesis of ellipticine and its derivatives

Abstract

The pyrido [4,3-b]carbazole alkaloid, ellipticine, was attracting considerable interest for many years due to its pronounced antitumor activity. We review the most important achievements in the field of ellipticine synthesis and its derivatives since 2012.

Synthesis of Diarylamines and Methylcarbazoles and Formal Total Synthesis of Alkaloids Ellipticine and Olivacine

“…This approach represents a new formal total synthesis of ellipticine ( 1 a ) through a short three‐step process for the efficient preparation of its known precursor carbazole 4 a [20] . Seemingly, it also constitutes a formal total synthesis of natural 9‐methoxyellipticine ( 1 b ), since carbazole 15 e has been previously employed as an efficient starting material during the last steps of the process, including 4 c as an intermediate [19f,20b,39,40] …”

Renal protective effect of ellipticine against streptozotocin induced diabetic nephropathy in rats via suppression of oxidative stress and inflammatory mediator

“…Ellipticine demonstrated anti-inflammatory effect against the lipopolysaccharide induces macrophages via targeting the JNK/AP-1 signaling pathway 24 . Current research has shown the synergistic effect of ellipticine in epithelial cells and that it alleviates the acute pancreatitis related with the acute lung injury in rats 21 , 23 , 24 . The anticancer activity of ellipticine was demonstrated through antioxidant actions 25 , 26 .…”

“…Ellipticine (alkaloid) isolated from the Ochrosia elliptica and belongs with the Apocynaceae family 21 . Ellipticine demonstrates anticancer effect, and already several derivatives of ellipticine are under the clinical trials [22][23][24] . Ellipticine demonstrated anti-inflammatory effect against the lipopolysaccharide induces macrophages via targeting the JNK/AP-1 signaling pathway 24 .…”

Total Synthesis of Olivacine and Ellipticine via a Lactone Ring-Opening and Aromatization Cascade

“…Since 1960s, total synthesis of olivacine and ellipticine has been a subject of many publications, as discussed in several review articles. ,,,− The majority of the methods for their syntheses rely on the late-stage D-ring cyclization, − whereas the late-stage C-ring − and B-ring cyclization strategies have been rarely reported. In their report in 1962, Cranwell and Saxton presented an effective and concise synthesis of ellipticine through the late-stage cyclization of the D-ring from lower rim .…”