68236-20-4Relevant articles and documents
Modified procedure for the synthesis of 2-chloroquinoline-3-carbaldehydes using phosphorus pentachloride
Romero, Angel H.
, p. 287 - 291 (2016)
An alternative, convenient, and efficient procedure for the synthesis of 2-chloroquinoline-3-carbaldehyde was carried out by the action of Vilsmeiers reagent on acetanilides using phosphorus pentachloride as chlorinating agent in place of phosphoryl chloride, obtaining good yields for activated acetanilides. The optimal conditions for this reaction requires only 4.5 equivalents of phosphorus pentachloride, 3 equivalents of N,N-dimethylformamide, and 1 equivalent of the corresponding acetanilide at 100 °C for approximately 4 h.
Tandem and transition metal-free synthesis of novel benzoimidazo-quinazoline as highly selective Hg2+ sensors
Shiri, Morteza,Heravi, Majid M.,Faghihi, Zeinab,Zadsirjan, Vahideh,Mohammadnejad, Masoumeh,Ranjbar, Maryam
, p. 2439 - 2449 (2018)
A one-pot procedure for the synthesis of novel planar aza-heterocycles possessing good fluorescence potencies was described. These benzo-imidazopyrimido[4,5-b]quinolone derivatives came from the reaction of 2-chloroquinoline-3-carboxaldehydes and 2-aminobenzimidazole using K2CO3 in DMF. The fluorescence study of these conjugated systems was also considered, which revealed that they have highly selective sensing of mercury. Consequently, to investigate another aspect of the reaction, a three-component reaction was developed by adding malononitrile to the aforementioned starting materials in the presence of l-proline under reflux condition in H2O/EtOH to provide amino-quinolin-3-yl-dihydrobenzo-imidazo-pyrimidine-3-carbonitriles in good yields.
Structure-based design, synthesis, biological evaluation, and molecular docking of novel 10-methoxy dibenzo[b,h][1,6]naphthyridinecarboxamides
Vennila,Selvakumar,Satish,Sunny,Madhuri,Elango
, p. 133 - 141 (2020/10/15)
10-methoxy dibenzo[b,h][1,6]naphthyridine carboxylic acid was successfully synthesized from 3-methoxyaniline by a new route. By utilizing a structure-based epharmacophore developed from the active site of 3-phosphoinositide-dependent kinase-1, a series of nine novel 10-methoxy dibenzo[b,h][1,6]naphthyridinecarboxamides was synthesized and characterized by different spectral techniques. Three of them are found to be active by screening against A549 cell line and showed significant anticancer activity when compared to a marketed lung cancer drug, pemetrexed. The molecular docking and in silico pharmacokinetic predictions provide detailed understanding for utilizing the dibenzo[b,h][1,6]naphthyridine scaffold in future drug discovery and development of PDK1 inhibitors.
Discovery of novel quinoline-based analogues of combretastatin A-4 as tubulin polymerisation inhibitors with apoptosis inducing activity and potent anticancer effect
Ibrahim, Tarek S.,Hawwas, Mohamed M.,Malebari, Azizah M.,Taher, Ehab S.,Omar, Abdelsattar M.,Neamatallah, Thikryat,Abdel-Samii, Zakaria K.,Safo, Martin K.,Elshaier, Yaseen A. M. M.
, p. 802 - 818 (2021/03/29)
A new series of quinoline derivatives of combretastatin A-4 have been designed, synthesised and demonstrated as tubulin polymerisation inhibitors. These novel compounds showed significant antiproliferative activities, among them, 12c exhibited the most potent inhibitory activity against different cancer cell lines (MCF-7, HL-60, HCT-116 and HeLa) with IC50 ranging from 0.010 to 0.042 μM, and with selectivity profile against MCF-10A non-cancer cells. Further mechanistic studies suggest that 12c can inhibit tubulin polymerisation and cell migration, leading to G2/M phase arrest. Besides, 12c induces apoptosis via a mitochondrial-dependant apoptosis pathway and caused reactive oxygen stress generation in MCF-7 cells. These results provide guidance for further rational development of potent tubulin polymerisation inhibitors for the treatment of cancer.Highlights A novel series of quinoline derivatives of combretastatin A-4 have been designed and synthesised. Compound 12c showed significant antiproliferative activities against different cancer cell lines. Compound 12c effectively inhibited tubulin polymerisation and competed with [3H] colchicine in binding to tubulin. Compound 12c arrested the cell cycle at G2/M phase, effectively inducing apoptosis and inhibition of cell migration.