131775-94-5Relevant academic research and scientific papers
The synthesis of benzo[h]quinolines as topoisomerase inhibitors
Kerry, Mark A.,Boyd, Gary W.,Mackay, Simon P.,Meth-Cohn, Otto,Platt, Louise
, p. 2315 - 2321 (1999)
A range of benzo[h]quinolines of potential biological interest have been prepared by'way of the 2-chloroand the 4-chlorobenzo[h]quinoline-3-carbaldehyde isomers.
Synthesis of novel 1,3,4-oxadiazole derivatives and their nucleoside analogs with antioxidant and antitumor activities
Fadda,Abdel-Rahman,El-Sayed,Zidan,Badria
, p. 856 - 864 (2011)
A series of new (1,3,4-oxadiazol-2-yl)-1H-benzo[h]quinolin-4-one derivatives were synthesized, including glucose and xylose hydrazones that were obtained by the reaction of hydrazides with monosaccharides. Cyclization of the sugar hydrazones with acetic anhydride afforded substituted oxadiazoline derivatives. The newly synthesized compounds were evaluated for their antioxidant properties and cytotoxicity, and showed moderate to high activities.
Synthesis of Fused Pyrimidinone and Quinolone Derivatives in an Automated High-Temperature and High-Pressure Flow Reactor
Tsoung, Jennifer,Bogdan, Andrew R.,Kantor, Stanislaw,Wang, Ying,Charaschanya, Manwika,Djuric, Stevan W.
, p. 1073 - 1084 (2018/06/18)
Fused pyrimidinone and quinolone derivatives that are of potential interest to pharmaceutical research were synthesized within minutes in up to 96% yield in an automated Phoenix high-temperature and high-pressure continuous flow reactor. Heterocyclic scaffolds that are either hard to synthesize or require multisteps are readily accessible using a common set of reaction conditions. The use of low-boiling solvents along with the high conversions of these reactions allowed for facile workup and isolation. The methods reported herein are highly amenable for fast and efficient heterocycle synthesis as well as compound scale-ups.
Novel quinolone-3-carboxylic acid derivatives as anti-HIV-1 agents: design, synthesis, and biological activities
Hajimahdi,Zabihollahi,Aghasadeghi,Ashtiani, S. Hosseini,Zarghi
, p. 1861 - 1876 (2016/10/03)
A new series of quinolone-3-carboxylic acids featuring different hydrophobic groups at N-1, C-2, C-7, and C-8 positions were synthesized and evaluated for their activity against single-cycle replicable HIV NL4-3 as inhibition rate of p24 expression in Hela cells cultures. Most of the synthesized compounds showed anti-HIV activity with no significant cytotoxicity at concentration of 100 μM. The most active compounds 4h, 4k, and 4j exhibited anti-HIV activity with an inhibition rate of 55, 71, and 84 %, respectively. A docking study using the crystallographic data available for PFV integrase including its complexes with Mg2+ and Raltegravir revealed that the active compounds could occupy same space near Raltegravir and interact with the Mg2+ ions in the active site. Thus, the anti-HIV activity of the synthesized compounds might involve a metal chelating mechanism. [InlineMediaObject not available: see fulltext.]
2,2-Bis(ethoxycarbonyl)vinyl (BECV) as a versatile amine protecting group for selective functional-group transformations
Ilangovan, Andivelu,Kumar, Rajendran Ganesh
supporting information; experimental part, p. 2938 - 2943 (2010/07/02)
A 2,2-Bis(ethoxycarbonyl) vinyl- (BECV) group was used for the selective protection of amines at room temperature in the presence of potentially interfering functional groups such as OH, SH, COOH as well as other NH 2 groups. Several functional group transformations such as esterification, O-alkylation, O-acylation, N-alkylation, N-acylation, S-alkylation can selectively be carried out in the presence of the BECV group. The selective deprotection of the BECV group was achieved in a short time using ethylenediamine at room temperature while several other functional groups such as benzoate, aliphatic esters, amides and ethers remain intact. The BECV group shows orthogonal stability against the common protecting groups such as Fmoc, Cbz and Boc.
Benzo(h)quinoline derivatives as G-quadruplex binding agents
Paritala, Hanumantharao,Firestine, Steven M.
scheme or table, p. 1584 - 1587 (2009/10/14)
G-quadruplexes are unusual structures formed from guanine-rich sequences of nucleic acids. G-quadruplexes have been postulated to play important roles in a number of biological systems including gene regulation and the inhibition of enzyme function. Recen
Evaluation of 3-carboxy-4(1H)-quinolones as inhibitors of human protein kinase CK2
Golub, Andriy G.,Yakovenko, Olexander Ya.,Bdzhola, Volodymyr G.,Sapelkin, Vladislav M.,Zien, Piotr,Yarmoluk, Sergiy M.
, p. 6443 - 6450 (2007/10/03)
Due to the emerging role of protein kinase CK2 as a molecule that participates not only in the development of some cancers but also in viral infections and inflammatory failures, small organic inhibitors of CK2, besides application in scientific research, may have therapeutic significance. In this paper, we present a new class of CK2 inhibitors-3-carboxy-4(1H)-quinolones. This class of inhibitors has been selected via receptor-based virtual screening of the Otava compound library. It was revealed that the most active compounds, 5,6,8-trichloro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (7) (IC 50 = 0.3 μM) and 4-oxo-1,4-dihydrobenzo[h]quinoline-3-carboxylic acid (9) (IC50 = 1 μM), are ATP competitive (Ki values are 0.06 and 0.28 μM, respectively). Evaluation of the inhibitors on seven protein kinases shows considerable selectivity toward CK2. According to theoretical calculations and experimental data, a structural model describing the key features of 3-carboxy-4(1H)-quinolones responsible for tight binding to CK2 active site has been developed.
The inhibition of factor inhibiting hypoxia-inducible factor (FIH) by β-oxocarboxylic acids
Banerji, Biswadip,Conejo-Garcia, Ana,McNeill, Luke A.,McDonough, Michael A.,Buck, Matthew R. G.,Hewitson, Kirsty S.,Oldham, Neil J.,Schofield, Christopher J.
, p. 5438 - 5440 (2008/01/27)
Cyclic β-oxocarboxylic acids inhibit factor inhibiting hypoxia-inducible factor via ligation to the active site iron. The Royal Society of Chemistry 2005.
