Synthesis and in vitro and in vivo anticancer activity of novel 3-methyl-5H-isoxazolo[5′,4′:5,6]pyrido[2,3-b]indoles

Synthesis and evaluation of bis(imino)anthracene derivatives as G-quadruplex ligands

“…22 The anti-cancer activity of indoles has also been shown with indole groups in isoxazolo[5′,4′:5,6]pyrido[2,3-b]indoles, which showed significant anticancer activity comparable to standard drugs however the mechanism of action and structure activity relationship is yet to be investigated. 23 The three groups that contained oxygen, sulphur and nitrogen, and nitrogen and oxygen, 1,3-benzodioxole, 2,5-dimethylthiazole and N-propylmorpholine respectively, showed a close linear correlation between their ability to stabilise G4 structure and IC 50 . They also, as a group had the best IC 50 values with 1,3-benzodioxole and 2,5-dimethyl thiazole as the best candidates for further testing.…”

Metal-Free and Regioselective Synthesis of Functionalized α-Carbolines via [3 + 3] Annulation of Morita–Baylis–Hillman Acetates of Nitroalkenes with Iminoindolines

“…Yellow solid; yield 66 mg, 95%; mp 180−182 °C; IR (film, cm −1 ) 3269 (m), 1718 (s); 1 H NMR (CDCl 3 , 400 MHz) δ 11.75 (br s, 1H), 7.97 (s, 1H), 7.80 (d, J = 8.0 Hz, 1H), 7.68 (d, J = 8.3 Hz, 2H), 7.68 (overlapped d, J = 8.0 Hz, 1H), 7.46 (t, J = 8.0 Hz, 1H), 7.13 (d, J = 8.3 Hz, 2H), 7.10 (overlapped t, J = 8.0 Hz, 1H), 4.80 (q, J = 6.8 Hz, 2H), 3.95 (s, 3H), 1.37 (t, J = 6.8 Hz, 3H); 13 C { 1 H} NMR (CDCl 3 , 100 MHz) δ 166. 2, 160.4, 152.7, 145.4, 143.0, 141.0, 130.9, 130.3, 128.0, 123.2, 120.2, 119.9, 118.1, 117.2, 114.4, 112.4, 62.0, 55.6, 14.5 (4-(4-Methoxyphenyl)-9-methyl-9H-pyrido [2,3-b]indol-2-yl)methanol (5). A slurry of LiAlH 4 (42 mg, 1.1 mmol, 1.1 equiv) in dry THF (5 mL) was cooled to 0 °C.…”

“…4 Also, several isoxazolo [5′,4':5,6]pyrido [2,3b]indoles have been synthesized by the Rajanarendar group, and many of them have shown potential anticancer activity (Figure 1). 5 α-Carboline based thiophene derivatives have also found use in organic semiconductors, in organic thin-film transistors, 6 and in phosphorescent organic light emitting devices. 7 Hence, the development of synthetic routes for the construction of α-carboline for applications in different fields is of considerable interest.…”

Bifunctional Brønsted Base Catalyzed [3 + 3] Annulations of Indolin-2-imines and α,β-Unsaturated Imides: An Enantioselective Approach to α-Carbolinones

“…As a privileged structural motif in drug discovery, α-carbolines (pyrido­[2,3- b ]­indoles) that incorporate pyridine and indole moieties have shown diverse biological activities . α-Carbolinones, one of the important oxidized analogues of α-carbolines, not only exist in a wide variety of bioactive drug leads but also exhibit good translational potential for the synthesis of complex molecules .…”