Antifungal properties of new series of quinoline derivatives

Musioł, Robert; Jampílek, Josef; Buchta, Vladimı́r; Silva, Luis; Niedbala, Halina; Podeszwa, Barbara; Palka, Anna; Majerz-Maniecka, Katarzyna; Oleksyn, Barbara J.; Polański, Jarosław

doi:10.1016/j.bmc.2006.01.016

Cited by 272 publications

(162 citation statements)

References 15 publications

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“…[1][2][3] The structural core of quinoline is often found in more complex natural products 4 and is frequently associated with biological activity, such as anticancer, 5 antifungal, 6 HIV-1 integrase inhibitors, 7 HIV protease inhibitors 8 antileishmanial activity, 9 NK-3 receptor antagonists 10 and pLT antagonists. [11][12][13] Our objectives were to synthesize a series of quinoline derivatives substituted at position 1 and 2 by a spacer linked with a series of amino acids and dipeptides as pLT antagonists regarded as important mediators of human bronchial asthma 14 .…”

Section: Introductionmentioning

confidence: 99%

Convenient syntheses of methyl 2-[2-(3-acetyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetamido] alkanoates and their O-regioisomers

Ali¹,

Fathalla²,

Rayes³

2008

Arkivoc

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Methyl 2-[2-(3-acetyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acet-amido] alkano-ate 7; Oregioisomers 12 and N-substituted dipeptides 14 were efficiently prepared by azide coupling of amino acid esters with the azide derivatives 5, 11 and 13, respectively. Further the N-substituted ester 7 reacted with N 2 H 4 .H 2 O to give the hydrazide 8 which was condensed with furan-2-carbaldehyde to exhibit the hydrazone 9.

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Section: Introductionmentioning

confidence: 99%

Convenient syntheses of methyl 2-[2-(3-acetyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetamido] alkanoates and their O-regioisomers

Ali¹,

Fathalla²,

Rayes³

2008

Arkivoc

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“…For background information on the pharmacological activity of quinoline derivatives, see: Elslager et al (1969); Font et al (1997); Kaminsky & Meltzer (1968); Musiol et al (2006); Nakamura et al (1999); Palmer et al (1993); Ridley (2002); Sloboda et al (1991); Tanenbaum & Tuffanelli (1980); Warshakoon et al (2006). For recent studies on quinoline-based anti-malarials, see: Andrade et al (2007); Cunico et al (2006); da Silva et al (2003); de Souza et al (2005).…”

Section: Related Literaturementioning

confidence: 99%

“…The majority of drugs used against malaria, such as chloroquine (Tanenbaum & Tuffanelli, 1980), mefloquine (Palmer et al, 1993), primaquine (Elslager et al, 1969) and amodiaquine (Ridley, 2002) possess a quinoline ring which has been the mainstay of malaria chemotherapy for much of the past 40 years (Font et al, 1997;Kaminsky & Meltzer, 1968;Musiol et al, 2006;Nakamura et al, 1999;Sloboda et al, 1991;Warshakoon et al, 2006). However, their effectiveness has been seriously eroded in recent years, mainly as a result of the development of parasite resistance (Ridley, 2002).…”

Section: S1 Commentmentioning

confidence: 99%

4-[(2-Chloroethyl)amino]quinolinium chloride monohydrate

et al. 2009

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Key indicators: single-crystal X-ray study; T = 120 K; mean (C-C) = 0.003 Å; R factor = 0.032; wR factor = 0.065; data-to-parameter ratio = 17.8.In the title salt hydrate, C 11 H 12 ClN 2 + ÁCl À ÁH 2 O, the quinolinium core is essentially planar (r.m.s. deviation = 0.027 Å ) with the chloroethyl side chain being almost orthogonal to the core [C-N-C-C torsion angle = À80.0 (3) ]. In the crystal packing, the water molecule bridges three species, forming donor interactions to two chloride anions and accepting a hydrogen bond from the quinolinium H atom. The chloride anion accepts a hydrogen bond from the amine N atom with the result that a two-dimensional supramolecular array is formed in the ac plane. A C-HÁ Á ÁCl interaction also occurs. Related literature

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“…A quinoline scaffold possesses unique physico-chemical properties and therefore it is present in many classes of biologically-active compounds expressing diverse effects [1][2][3][4][5][6]. In addition, according to the results reported recently, some quinoline derivatives and their analogues/isosteres also showed noteworthy herbicidal activities [7][8][9][10][11][12][13][14][15][16][17][18][19][20].…”

Section: Introductionmentioning

confidence: 99%

Preparation and Herbicidal Activity of Halogenated 8-Hydroxyquinoline-2-carboxanilides

Kos

Machalova

Peško

et al. 2013

Proceedings of the 17th International Electronic Conference on Synthetic Organic Chemistry

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Abstract:In this study a series of twelve ring-substituted 8-hydroxyquinoline-2-carboxanilides was prepared and characterized. The discussed compounds were prepared by using microwave-assisted synthesis. The compounds were tested for their activity related to inhibition of photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The compounds were found to inhibit PET in photosystem II. Significant PET-inhibiting activity was observed for meta-substituted compounds showing IC 50 values close to that of photosystem II herbicide DCMU (3-(3,4-dichlorophenyl)-1,1-dimethylurea, IC 50 = 1.9 μmol/L). N-(3-Fluorophenyl)-8-hydroxyquinoline-2-carboxamide showed the highest PET inhibition. The activity of meta-and para-substituted compounds strongly decreased with lipophilicity increase and electron-withdrawing effect. No influence of any of these parameters on PET-inhibiting activity of ortho-substituted compounds was observed.

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Antifungal properties of new series of quinoline derivatives

Cited by 272 publications

References 15 publications

Convenient syntheses of methyl 2-[2-(3-acetyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetamido] alkanoates and their O-regioisomers

Convenient syntheses of methyl 2-[2-(3-acetyl-4-methyl-2-oxo-1,2-dihydroquinolin-1-yl)acetamido] alkanoates and their O-regioisomers

4-[(2-Chloroethyl)amino]quinolinium chloride monohydrate

Preparation and Herbicidal Activity of Halogenated 8-Hydroxyquinoline-2-carboxanilides

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