An easy synthetic protocol for imidazo‐1,4‐oxazines and evaluation of their toxicities

Abstract

Imidazo-1,5-alkynyl alcohol derivatives were synthesized, and they were cyclized to imidazo-1,4-oxazines by means of cesium carbonate. Propargyl-allene isomerization was examined, and the reaction mechanism was proposed. Moreover, cytotoxicity of synthesized molecules against LN405 cell lines was investigated by means of structure-activity relationship (SAR). With SAR study, toxicities of some functional groups have been shown. In addition, two lead compounds were tested against DNA damaging. 2 of 12 | KUZU et al. 3.22 | [1-(Prop-2-yn-1-yl)-4-(thiophen-2-yl)-1H-imidazol-2-yl](thiophen-2-yl)methanol (7h) Brown solid, m.p.: 145-146°C; yield: 80%. 1 H NMR (400 MHz, d 6 -DMSO) δ = 7.57 (s, 1H, H-7), 7.47 (dd, J 15,17 = 1.26 Hz, J 15,16 = 5.05 Hz, 1H, H-15), 7.34 (dd,

Synthesis of Indolizines by Dimerization of N‐Propargylated Pyrroles via Allene Intermediates

“…Initially, based on our previous works on the synthesis of azaheterocyclic compounds, [15] we chose N ‐propargyl‐C‐2‐substituted‐pyrroles as the starting material, synthesized as described in our previous report [16a–e] . Reaction of 13a with a base provided the indolizine derivative 15a in relatively good yield beside the allene 16 and the hydrolysis compound 17 .…”

A novel class for carbonic anhydrases inhibitors and evaluation of their non‐zinc binding

“…4.1.2 | Synthesis of compounds 11a-p [58] The commercially available acetyl-substituted aromatic compounds…”

“…and 12b [58] The obtained imidazole derivatives 11f and 11g (1 mmol) were dissolved in methanol, and NaBH 4 (2 mmol) was added to the solution at room temperature. The solution was stirred for 2 h; the reaction completion was controlled by TLC and the mixture was recrystallized with water.…”

Copper-Catalyzed Synthesis of Fused Imidazopyrazine N-Oxide Skeletons

“…N-Propargyl 2,4-disubstituted imidazoles 1a-g and Npropargyl 2-substituted imidazoles 3a and 3h were synthesized by methods reported in the literature [for details of the reactions, see the Supplementary Information (SI), Scheme S3]. [16][17][18] During the propargylation reaction to form 1a-g, 3a, and 3h, the N-1 atom was propargylated exclusively. To determine the structure of the favored N-propargylated isomer, we calculated their relative enthalpies and Gibbs free energies (SI; Figure S1).…”

“…FT-IR(ATR cm-1): 3437, 3103, 2981, 2903, 2834, 2357, 2016, 1674, 1600, 1513, 1462, 1418, 3.77 (s, 6H, OCH3), 3.73 (s, 6H, OCH3), 1.61 (s,3H,CH3). 13 C-NMR (100 MHz, DMSO-d6) δ 151.…”