Synthesis and Antiproliferative Evaluation of Amide-Containing Anthraquinone, Xanthone, and Carbazole

Abstract

Certain amide-containing anthraquinone, xanthone, and carbazole derivatives have been synthesized and evaluated in vitro for their antiproliferative activities against a panel of human cancer cell lines including nasopharyngeal carcinoma (NPC-TW01), lung carcinoma (NCI-H661), and leukemia (Jurkat). Among them, 2-(9,10-dioxo-9,10-dihydroanthracen-2-yloxy)-N-(naphthalen-2-yl)acetamide (13) was the most active against NPC-TW01 with an IC 50 value of 2.62 µM while its xanthone and dibenzofuran counterparts, 14 and 15, were inactive with an IC 50 value of 16.10 and 11.09 µM, respectively. Studies on NPC-TW01 cell cycle distribution revealed that compound 13 inhibited proliferation of NPC-TW01 by the alteration of cell division and the accumulation of cells in G 0 /G 1 phase.

Carbazole scaffolds in cancer therapy: a review from 2012 to 2018

“…Amide-containing carbazole derivatives 7a–d and 8 (Figure 12) have been synthesized and their in vitro anti-proliferative activities against NPC-TW01 (nasopharyngeal carcinoma), NCI-H661 (lung carcinoma) and Jurkat (leukaemia) cell lines were evaluated. All carbazole derivatives were inactive or weakly active, with IC 50 values ranging from 11.09 to 42.77 µM 39 .…”

Recent synthetic strategies for the construction of functionalized carbazoles and their heterocyclic motifs enabled by Lewis acids

“…The selectively collected list of carbazoles and annulated carbazoles as well as their bio-applications are detailed and summarised in the Table 1. 142–179…”

Synthesis and antiproliferative evaluation of oxime, methyloxime, and amide‐containing quinazolinones

“…For the past few years, we have been interested in the design and synthesis of novel heterocyclic compounds as potential anti‐NPC agents . Among them, N ‐(biphenyl‐4‐yl)‐2‐(2‐oxo‐1,2‐dihydroquinolin‐7‐yloxy)acetamide ( I ) and N ‐(naphthalen‐2‐yl)‐2‐(4‐oxo‐2‐phenyl‐4 H ‐chromen‐7‐yloxy)acetamide ( II ) were found to be selectively active against the growth of NPC‐TW01 with IC 50 values of <10 and 1.37 μM, respectively.…”

“…More recently, we have prepared certain N ‐(naphthalen‐2‐yl)acetamide derivatives and evaluated in vitro for their antiproliferative activities against a panel of human cancer cell lines. Among them, N ‐(naphthalen‐2‐yl)‐2‐(2‐oxo‐1,2,3,4‐tetrahydroquinolin‐6‐yloxy)acetamide ( III ) and 2‐(9,10‐dioxo‐9,10‐dihydroanthracen‐2‐yloxy)‐ N ‐(naphthalen‐2‐yl)acetamide ( IV ) were found to have selective antiproliferative activities against NPC‐TW01 with IC 50 values of 0.6 and 2.62 μM, respectively. In continuation of our studies to explore active and selective anti‐NPC agents and establish structure–activity relationships, the present report describes the preparation of certain amide‐containing quinazolinone derivatives (Figure ).…”