438590-10-4Relevant academic research and scientific papers
Cascade embedding triethyltryptophanium iodide ionic liquid (TrpEt3+I?) on silicated titanomagnetite core (Fe3-xTixO4-SiO2@TrpEt3+I?): A novel nano organic–inorganic hybrid to prepare a library of 4-substituted quinoline-2-carboxylates and 4,6-disubstituted quinoline-2-carboxylates
Nikoofar, Kobra,Molaei Yielzoleh, Fatemeh
, p. 1549 - 1562 (2021)
A library of substituted quinolone-2-carboxylates (4,6-disubstituted quinolone-2-carboxylates, 6-substituted quinoline dialkyl-2,4-dicarboxylates, and 6-substituted 4-[2-methoxy-2-oxoethyl]quinoline-2-methylcarboxylates) was obtained through different scopes of one-pot and one-step MCRs such as (a) three-component reaction of aromatic amines, dialkyl acetylenedicarboxylates, and terminal alkenes/ketones; (b) pseudo three-component reaction of anilines and dialkyl acetylenedicarboxylates; and (c) pseudo three-component reaction of anilines and methyl propiolate under solvent-free conditions at 100°C. The promoter of these annulation processes is a novel inorganic–organic core–shell that was obtained from silicated titanomagnetite, tryptophan amino acid, and ethyl iodide. The tryptophan embedded on the silicated titanomagnetite core (Fe3-xTixO4-SiO2) followed by alkylation with ethyl iodide subsequently result in in situ preparation of triethyltryptophanium iodide ionic liquid (TrpEt3+I?). The final nanohybrid (Fe3-xTixO4-SiO2@TrpEt3+I?) was characterized by field-emission scanning electron microscope, EDAX, FT-IR, TGA/DTG, vibrating sample magnetometer, and X-ray fluorescence techniques. The highlighted features of the protocol are as follows: (a) synthesis of a vast range of substituted quinolines through a straightforward method from simple substrates under solvent-free conditions, (b) utilizing various scopes of functionalities as substrates, (c) simple separation of the nano promoter via an external magnet, (d) regioselectivity in the cascade annulation procedure, and (e) recovery and reusability of the nanocomposite within three runs without significant activity loss.
GLUCOSE TRANSPORT INHIBITORS
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Page/Page column 174; 175, (2017/01/02)
The present invention relates to quinoline-4-carboxamide derivatives of Formula (I) that selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds,
GLUCOSE TRANSPORT INHIBITORS
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, (2015/07/07)
The present invention relates to chemical compounds that selectively inhibit glucose transporter 1 (GLUT1), to methods of preparing said compounds, to pharmaceutical compositions and combinations comprising said compounds, to the use of said compounds for
Synthesis and in vitro pharmacology of substituted quinoline-2,4-dicarboxylic acids as inhibitors of vesicular glutamate transport
Carrigan, Christina N.,Bartlett, Richard D.,Esslinger, C. Sean,Cybulski, Kimberly A.,Tongcharoensirikul, Pakamas,Bridges, Richard J.,Thompson, Charles M.
, p. 2260 - 2276 (2007/10/03)
The vesicular glutamate transport (VGLUT) system selectively mediates the uptake of L-glutamate into synaptic vesicles. Uptake is linked to an H+-ATPase that provides coupling among ATP hydrolysis, an electrochemical proton gradient, and glutamate transport. Substituted quinoline-2,4-dicarboxylic acids (QDCs), prepared by condensation of dimethyl ketoglutaconate (DKG) with substituted anilines and subsequent hydrolysis, were investigated as potential VGLUT inhibitors in synaptic vesicles. A brief panel of substituted QDCs was previously reported (Carrigan et al. Bioorg. Med. Chem. Lett. 1999, 9, 2607-2612)1 and showed that certain substituents led to more potent competitive inhibitors of VGLUT. Using these compounds as leads, an expanded series of QDC analogues were prepared either by condensation of DKG with novel anilines or via aryl-coupling (Suzuki or Heck) to dimethyl 6-bromoquinolinedicarboxylate. From the panel of almost 50 substituted QDCs tested as inhibitors of the VGLUT system, the 6-PhCH=CH-QDC (Ki = 167 μM), 6-PhCH2CH2-QDC (Ki = 143 μM), 6-(4′-phenylstyryl)-QDC (Ki = 64 μM), and 6-biphenyl-4-yl-QDC (Ki=41 μM) were found to be the most potent blockers. A preliminary assessment of the key elements needed for binding to the VGLUT protein based on the structure-activity relationships for the panel of substituted QDCs is discussed herein. The substituted QDCs represent the first synthetically derived VGLUT inhibitors and are promising templates for the development of selective transporter inhibitors.
Quinoline-2,4-dicarboxylic acids: Synthesis and evaluation as inhibitors of the glutamate vesicular transport system
Carrigan, Christina N.,Esslinger, C. Sean,Bartlett, Richard D.,Bridges, Richard J.,Thompson, Charles M.
, p. 2607 - 2612 (2007/10/03)
Twenty-six quinoline-2,4-dicarboxylic acids (QDC's) were synthesized by a modified Doebner-von Miller pathway and tested as inhibitors against the glutamate vesicular transport (GVT) protein. The QDC's were active as inhibitors with the most potent QDC's found to contain halogens at the 6-/8-position, a hydroxyl at the 8-position, or a tethered aromatic moiety at the 6- or 7-position of the quinoline.
