Quinoline and ferrocene conjugates: Synthesis, computational study and biological evaluations

O ‐ and N‐regioisomers of new quinoline‐ferrocene conjugates exhibit different cytostatic activity. NovelO‐alkylated quinoline andN‐alkylated 4‐quinolone derivatives attached to the ferrocene moiety through 4,1‐ (7a –d,8a –d and12a –d) and 1,4 ‐disubstituted (9a,9b,10a and10b) 1,2,3 ‐triazole moiety were synthesized. The observed regioselectivity ofO‐ vs.N‐alkylation was explored by the use of NMR and computational techniques. Among theN‐alkylated derivatives, the quinolone‐ferrocene conjugate9a displayed marked activities against chronic myeloid leukemia in blast crisis (K562) and Burkitt lymphoma (Raji). The 6 ‐chloroquinolone‐ferrocene conjugate12c, with selective inhibitory activity on Raji cells and no cytostatic effect on normal MDCK1 cells was highlighted as the most promising anticancer organometallic complex in a group ofO‐alkylated quinolines.

Source: Applied Organometallic Chemistry - November 19, 2018 Category: Chemistry Authors: Silvija Mara čić, Jasmina Lapić, Senka Djaković, Teuta Opačak‐Bernardi, Ljubica Glavaš‐Obrovac, Valerije Vrček, Silvana Raić‐Malić Tags: FULL PAPER Source Type: research