351-83-7Relevant articles and documents
A Facile Regioselective Aromatic Fluorination of N-Aryl-N-hydroxyamides with Diethylaminosulfur Trifluoride (DAST)
Kikugawa, Yasuo,Matsumoto, Kazuhiro,Mitsui, Kimiyo,Sakamoto, Takeshi
, p. 921 - 922 (1992)
Treatment of N-aryl-N-hydroxyamides with diethylaminosulfur trifluoride (DAST) under conventional reaction conditions results in removal of the hydroxy function and introduction of a fluorine atom at the para position of the aromatic ring, in high yield.
Arylquinolinecarboxamides: Synthesis, in vitro and in silico studies against Mycobacterium tuberculosis
Bokosi, Fostino R. B.,Beteck, Richard M.,Jordaan, Audrey,Seldon, Ronnet,Warner, Digby F.,Tshiwawa, Tendamudzimu,Lobb, Kevin,Khanye, Setshaba D.
supporting information, p. 2140 - 2151 (2021/07/21)
A series of fourteen 6-substituted-2-(methoxyquinolin-3-yl) methyl)-N-(pyridin-3-ylmethyl) benzamides was prepared from commercially available anilines in five simple and convenient synthetic steps. The structures of all new products were confirmed by routine spectroscopic methods: IR, 1H and 13C NMR, and HRMS (electrospray ionization). The resulting arylquinolinecarboxamides were subjected to biological screening assay for in vitro inhibitory activity against Mycobacterium tuberculosis (Mtb) H37Rv strain. Several compounds exhibited modest antitubercular activity with compounds 8–11, 15 and 19 exhibiting MIC90 values in the range of 32–85 μM. The antitubercular data suggested that inhibition of Mtb can be imparted by the introduction of a non-polar substituent on C-6 of the quinoline scaffold. Further, to understand the possible mode of action of the series, the reported compounds and bedaquiline were subjected to in silico docking studies against MtbATPase to determine their potential to interfere with the mycobacterial adenosine triphosphate (ATP) synthase. The results showed that these compounds have the potential to serve as antimycobacterial agents. In silico ADME pharmacokinetic prediction results showed the ability of these arylquinolinecarcboxamides to be absorbed, distributed, metabolized and excreted efficiently.
Synthesis, crystal structure, anticancer and molecular docking studies of quinolinone-thiazolidinone hybrid molecules
Krishnappagowda, Lokanath Neratur,Kumar, Vasantha,Pai, Vinitha R.,Poojary, Boja,Rai, Vaishali M.,Shivalingegowda, Naveen,Udupi, Vishwanatha
, (2021/08/12)
A new series of quinolone-thiazolidinone hybrid molecules 8a-o were prepared. Quinoline compounds were synthesized by Meth-Cohn synthesis and were condensed with 2,3-disubstituted thiazolidinone. These molecules were screened for their anticancer activities against MDA-MB-231 and MCF-7 cell line using MTT assay. Potent compounds were tested for their cytotoxicity on normal HEK 293 cell lines and most potent compound was tested for its cell cycle analysis. Molecular docking and molecular dynamic studies were performed on human N-acetyl transferase (hNAT-1) protein using Schrodinger molecular docking toolkit. Compound 8n emerged as potent with IC50 8.16?μM against MDA-MB-231 cell line followed by 8e with IC50 17.68?μM. Compound 8n arrested cell cycle at G2/M phase and was non-toxic to human normal kidney cell line. The potent compound 8n binds well with human NAT-1 protein with remarkable hydrogen bonding and π–π interactions. Molecular dynamic studies of 8n further confirm the target for these molecules. Target quinolinone-thiazolidinones were found to be new class of compounds targeting hNAT-1 and can serve as new lead compounds in drug discovery.
