6059-31-0Relevant academic research and scientific papers
Design, synthesis and biological evaluation of novel acridine and quinoline derivatives as tubulin polymerization inhibitors with anticancer activities
Ren, Yichang,Ruan, Yong,Cheng, Binbin,Li, Ling,Liu, Jin,Fang, Yuyu,Chen, Jianjun
, (2021/08/30)
A series of acridine and quinoline derivatives were designed and synthesized based on our previous work as novel tubulin inhibitors targeting the colchicine binding site. Among them, compound 3b exhibited the highest antiproliferative activity with an IC50 of 261 nM against HepG-2 cells (the most sensitive cell line). In addition, compound 3b was able to suppress the formation of HepG-2 colonies. Mechanism studies revealed that compound 3b effectively inhibited tubulin polymerization in vitro and disrupted microtubule dynamics in HepG-2 cells. Furthermore, compound 3b inhibited the migration of cancer cells in a dose dependent manner. Moreover, compound 3b induced cell cycle arrest in G2/M phase and led to cell apoptosis. Finally, docking studies demonstrated that compound 3b fitted nicely in the colchicine binding site of tubulin and overlapped well with CA-4. Collectively, these results suggested that compound 3b represents a novel tubulin inhibitor deserving further investigation.
Preparation method of intermediate for leukemia treatment medicines
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Paragraph 0071; 0072; 0073; 0074; 0075, (2019/01/23)
The invention belongs to the technical field of chemical medicines, and specifically relates to a preparation method of an intermediate for leukemia treatment medicines. The method comprises the stepsof supporting N-[3-(triethoxysilyl)propyl]-4,5-dihydroi
Trifluoroacetic acid in 2,2,2-trifluoroethanol facilitates SNAr reactions of heterocycles with arylamines
Carbain, Benoit,Coxon, Christopher R.,Lebraud, Honorine,Elliott, Kristopher J.,Matheson, Christopher J.,Meschini, Elisa,Roberts, Amy R.,Turner, David M.,Wong, Christopher,Cano, Celine,Griffin, Roger J.,Hardcastle, Ian R.,Golding, Bernard T.
supporting information, p. 2311 - 2317 (2014/03/21)
Small-molecule drug discovery requires reliable synthetic methods for attaching amino compounds to heterocyclic scaffolds. Trifluoroacetic acid-2,2,2-trifluoroethanol (TFA-TFE) is as an effective combination for achieving SNAr reactions between
Solvent- and chromatography-free amination of π-deficient nitrogen heterocycles under microwave irradiation. A fast, efficient and green route to 9-aminoacridines, 4-aminoquinolines and 4-aminoquinazolines and its application to the synthesis of the drugs amsacrine and bistacrine
Staderini, Matteo,Cabezas, Nieves,Bolognesi, Maria Laura,Menéndez, J. Carlos
, p. 1024 - 1030 (2013/02/23)
Focused microwave irradiation of equimolecular mixtures of 9-chloroacridines, 4-chloroquinolines and 4-chloroquinazolines with amines in the presence of 2 equiv of phenol allows the general, fast and high-yielding synthesis of aminated heterocycles, with a very broad scope in terms of amine structure (aromatic, linear primary aliphatic, α-branched primary aliphatic, secondary aliphatic and diamines). Workup consisted of a simple washing with water and purification could be achieved by crystallization, avoiding the use of organic solvents in extraction and chromatographic purification steps. This protocol provides a solution to the long-standing synthetic problem of achieving a practical and efficient method for the amination of π-deficient nitrogen heterocycles for medicinal chemistry applications.
Microwave-accelerated solvent- and catalyst-free synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles
Motiwala, Hashim F.,Kumar, Raj,Chakraborti, Asit K.
, p. 369 - 374 (2008/02/11)
An efficient synthesis of 4-aminoaryl/alkyl-7-chloroquinolines and 2-aminoaryl/alkylbenzothiazoles has been developed by microwave-accelerated regioselective aromatic nucleophilic substitution of 4,7-dichloroquinoline and 2-chlorobenzothiazole with aromatic and aliphatic amines under solvent-free conditions in the absence of any added protic or Lewis acid catalyst. Chemoselective reaction with the amino group in preference to the phenolic hydroxy group was observed. Thus, the treatment of 4,7-dichloroquinoline (1 equiv.) with a mixture of aniline (2 equiv.) and phenol (2 equiv.) afforded exclusive formation of 4-aminophenyl-7-chloroquinoline. When 4,7-dichloroquinoline (1 equiv.) was separately treated with 2-aminophenol (2 equiv.) and 4-aminophenol (2 equiv.), 4-(2'-hydroxyphenyl)-7-chloroquinoline and 4-(4'-hydroxyphenyl)-7-chloroquinoline, respectively, were formed. CSIRO 2007.
