35478-79-6Relevant academic research and scientific papers
Direct C-3-alkenylation of quinolones via palladium-catalyzed C-H functionalization
Li, Mingzong,Li, Liangxi,Ge, Haibo
, p. 2445 - 2449 (2010)
An unprecedented C-3-alkenylation of quinolones was reported through palladium-catalyzed C-H functionalization with 1% catalyst loading. This method provides an efficient route to a variety of new quinolone derivatives.
Cu(I)-Catalyzed Alkynylation of Quinolones
Maestro, Aitor,Lemaire, Sebastien,Harutyunyan, Syuzanna R.
supporting information, p. 1228 - 1231 (2022/02/14)
Herein we report the first alkynylation of quinolones with terminal alkynes under mild reaction conditions. The reaction is catalyzed by Cu(I) salts in the presence of a Lewis acid, which is essential for the reactivity of the system. The enantioselective version of this transformation has also been explored, and the methodology has been applied in the synthesis of the enantioenriched tetrahydroquinoline alkaloid cuspareine.
Highly Enantioselective Catalytic Addition of Grignard Reagents to N-Heterocyclic Acceptors
Guo, Yafei,Harutyunyan, Syuzanna R.
supporting information, p. 12950 - 12954 (2019/08/07)
General methods to prepare chiral N-heterocyclic molecular scaffolds are greatly sought after because of their significance in medicinal chemistry. Described here is the first general catalytic methodology to access a wide variety of chiral 2- and 4-substituted tetrahydro-quinolones, dihydro-4-pyridones, and piperidones with excellent yields and enantioselectivities, utilizing a single catalyst system.
METHODS FOR TREATING GASTRIC AND PANCREATIC MALIGNANCIES
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, (2012/02/13)
The invention provides methods and pharmaceutical compositions for treating pancreatic cancer or gastric cancer or a metastasis thereof.
Synthesis and biological evaluation of new heterocyclic quinolinones as anti-parasite and anti-HIV drug candidates
Darque, Albert,Dumetre, Aurelien,Hutter, Sebastien,Casano, Gilles,Robin, Maxime,Pannecouque, Christophe,Azas, Nadine
supporting information; experimental part, p. 5962 - 5964 (2010/06/17)
We have synthesized quinolinones with potential antiparasitic and anti-HIV activities by an original two-step method involving microwave irradiation and have evaluated their activities against Plasmodium falciparum, Leishmania donovani, Trichomonas vaginalis, and HIV. None of the tested compounds had been previously described using this method of synthesis. One of the compounds had interesting antiparasitic and anti-HIV activity, which could be improved by substitution with different radicals.
Novel and convenient synthesis of 4(1H)quinolones
Tois, Jan,Vahermo, Mikko,Koskinen, Ari
, p. 735 - 737 (2007/10/03)
A rapid two-step synthesis of 4(1H)quinolones is described. The first step involves condensation of o-nitroacetophenone with N,N-dimethylformamide dimethylacetal yielding highly crystalline enamines. In the second step a reductive cyclization is achieved
5-(2-Aminoethyl)dibenzo[c,h][1,6]naphthyridin-6-ones: Variation of N-alkyl substituents modulates sensitivity to efflux transporters associated with multidrug resistance
Ruchelman, Alexander L.,Houghton, Peter J.,Zhou, Nai,Liu, Angela,Liu, Leroy F.,LaVoie, Edmond J.
, p. 792 - 804 (2007/10/03)
5H-8,9-Dimethoxy-5-(2-N,N-dimethylaminoethyl)-2,3-methylenedioxydibenzo[c, h]-[1,6]naphthyridin-6-one (ARC-111) has potent TOP1-targeting activity and pronounced antitumor activity. Several analogues of ARC-111 were synthesized with NH2, N-alkyl, N,N-dialkyl, pyrrolidinyl, piperidinyl, and piperazinyl substituents at the 2-position of the 5-ethyl group. The relative TOP1-targeting activity and cytotoxicity of these structural analogues were assessed in RPMI8402 and P388 tumor cells and their camptothecin-resistant variants CPT-K5 and P388/CPT45, respectively. Potent TOP1-targeting activity was retained within a series of mono N-alkyl analogues that included NHCH 2CH3, NHCH(CH3)2, and NHC(CH 3)3. TOP1-targeting activity was diminished by the presence of a N-benzyl moiety. In a comparison of a series of N-alkyl-N-isopropyl analogues, activity decreased in the order CH3 > CH2CH3 > CH-(CH3)2. Cytotoxicity in RPMI8402 and P388 did correlate with TOP1-targeting activity. Cytotoxic activity was also determined in KB3-1 cells and its variants KB/V-1 and KBH5.0. As KB/V-1 cells overexpress MDR1 and KBH5.0 cells overexpress BCRP, decreased cytotoxicity in these cell lines relative to the parent cell line is indicative of compounds that are substrates for these efflux transporters. In view of their diminished cytotoxicity in KB/V-1 cells, it appears that the likely demethylated metabolites of ARC-111, i.e., where NH2 or NHCH3 replaces the N(CH3)2 at the 2-position of the 5-ethyl substituent, are substrates for MDR1. In contrast, no significant difference in cytotoxicity among these three cell lines was observed with other N-alkyl analogues, including NHC2H5, NHCH(CH 3)2, NHC(CH3)3, N(CH 3)2, N(CH2CH3)2, NCH 3(CH-(CH3)2), and either the pyrrolidinyl or the piperidinyl analogues. The 2-(piperazinyl) analogues were associated with diminished cytotoxicity in KB/V-1 cells, suggesting that the second basic amino substituent is associated with their recognition as substrates by MDR1. Comparative studies on the antitumor activity of ARC-111 and its N-demethylated derivatives (the NHCH3 and NH2 analogues) against SJ-BT45 medulloblastoma xenografts in seid mice revealed that the secondary amine metabolite is at least as active as ARC-111 in vivo, although the primary amine derivative was significantly less potent.
Process for producing quinolone derivatives
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, (2008/06/13)
The present invention relates to a process for producing a 4-quinolone derivative, comprising allowing an o-aminoacetophenone derivative to react with a formic acid in an aprotic solvent in the presence of a suitable base, and adding a protic solvent to the reaction mixture. This is a simple process for producing 4-quinolone derivatives, applicable to large-scale commercial production.
