Abstract
Three series of fused pyrrolophenanthroline derivatives were designed as analogues of phenstatin and synthesized in two steps starting with 1,7-phenanthroline, 4,7-phenanthroline and 1,10-phenanthroline, respectively. Two (Compounds 8a and 11c) of the four compounds tested against a panel of sixty human cancer cell lines of the National Cancer Institute (NCI) exhibited significant growth inhibition activity on several cell lines. Compound 11c showed a broad spectrum in terms of antiproliferative efficacy with GI50 values in the range of 0.296 to 250 μM. Molecular docking studies indicated that Compounds 8a and 11c are accommodated in the colchicine binding site of tubulin in two different ways.
Highlights
Phenanthrolines are versatile moieties which have found use in many applications [1,2,3] due to a wide variety of interesting properties
Compounds 5a–d were successfully synthesized using a two-step procedure starting from 1,7-phenanthroline 1
The results show that the two compounds, 8a and 11c, inhibit cell proliferation in several cancer cell lines, the derivative 11c being the most active and showing cytotoxic activity against the COLO205, MDA-MB-435 and A498 cell lines
Summary
Phenanthrolines are versatile moieties which have found use in many applications [1,2,3] due to a wide variety of interesting properties (complexation [1,2,3], luminescence [1,2,4], biological activities [4,5,6,7], semiconductors [8,9,10]). These polycyclic compounds are naturally occurring in morphine alkaloids, sterols or hormones [11], which makes the phenanthroline scaffold an excellent choice in the generation of unique bioactive compounds. Our group reported several fused pyrrolo [1,7] or [4,7] phenanthrolines which showed moderate antiproliferative activity [15,16,17]
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