Antimitotic activities of 2-phenylindole-3-carbaldehydes in human breast cancer cells

Well‐defined NHCPd complex‐mediated intermolecular direct annulations for synthesis of functionalized indoles (NHC = N‐hetero‐cyclic carbene)

“…According to the above-mentioned general procedure, the following indole derivatives were obtained and their m.p., 1 H-and 13 C-NMR were identical to those described in the literature. 2-Phenyl-1H-indole (entry 1, Table 2, in 68 and 66% yield), [26] 2-(4 -methyl)phenyl-1H-indole (entry 2, Table 2, in 67 and 62% yield), [27] 2-(4 -fluoro)phenyl-1H-indole (entry 3, Table 2, in 62 and 68% yield), [27] 2-(4 -methoxy)phenyl-1H-indole (entry 4, Table 2, in 65 and 58% yield), [28] 2,3,4,9-tetrahydro-1H-carbazole (entry 5, Table 2, in 98 and 92% yield), [29] 6,11-dihydro-5H-benzo[a]carbazole (entry 6, Table 2, in 69 and 65% yield), [30] 2-ethyl-3-methyl-1H-indole (entry 7, Table 2, in 81 and 80% yield), [31] 5-methyl-2-phenyl-1H-indole (entry 8, Table 2, in 70% yield), [27] 5-methyl-2-(4 -methyl)phenyl-1H-indole (entry 9, Table 2, in 72% yield), [32] 5-methyl-2-(4 -fluoro)phenyl-1H-indole (entry 10, Table 2, in 77% yield), [33] 6-methyl-2,3,4,9-tetrahydro-1H-carbazole (entry 11, Table 2, in 92% yield), [31] 8-methyl-6,11-dihydro-5H-benzo[a]carbazole (entry 12, Table 2, in 69% yield), [34] 8-methyl-5,10-dihydroindeno[1,2-b]indole (entry 13, Table 2, in 57% yield), [35] 4-methyl-2-phenyl-1H-indole (entry 14, Table 2, in 61 and 55% yield), [36] 5-methyl-2,3,4,9-tetrahydro-1H-carbazole (entry 16, Table 2, in 87 and 80% yield), [37] 2-(pyridin-4-yl)-1H-indole (entry 18, Table 2, in 86% yield). [38] According to the same procedure, 4-methyl-2-(4 -fluoro)phenyl-1H-indole (entry 15, …”

Fragment-based QSAR: perspectives in drug design

“…On the other hand, the characterization of the chemical space is an important factor to be considered in order to define the applicability of the constructed HQSAR models. To evaluate this crucial component, we have created statistically robust HQSAR models for a set of 180 indole derivatives presenting potent anticancer activity as a result of their ability to bind to the colchicine site and to inhibit tubulin polymerization (results not shown) [51][52][53][54]. Afterwards, we have analyzed and compared a series of HQSAR prediction statistics to provide meaningful insights that can be used for the determination of optimal cutoff values in VS procedures.…”

CoMFA and docking studies of 2-phenylindole derivatives with anticancer activity

“…In addition to its potent cytotoxicity, CA-4 is one of the few tubulin targeting agents reported to have selective vascular-disrupting activity [11,12]. Recently, von Angerer and coworkers have synthesized a series of 2-phenylindole derivatives and assessed their anticancer activities in human breast cancer cell lines [13][14][15]. They found that these compounds prevent the polymerization of the a/b-tubulin dimers to functional microtubules by binding to the colchicine-binding site and all have pronounced cytotoxicity, demonstrating the great potential of developing 2-phenylindole derivatives as a new class of anticancer drug.…”