Antiprotozoal 4-aryloxy-2-aminoquinolines and related compounds

Markees, D. G.; Dewey, Virginia C.; Kidder, George W.

doi:10.1021/jm00296a048

Cited by 107 publications

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“…Quinoline derivatives are important owing to their wide occurrence in natural products and in biologically active compounds (Markees et al, 1970;Campbell et al, 1988;Kalluraya & Sreenivasa, 1998). The pyrimidine nucleus also plays an important role in the medicinal chemistry and is reported to possess a broad spectrum of biological activities such as antimicrobial, anti-inflammatory, anthelmintic, anti HIV, antitubercular properties (Prasad et al, 2008;Vaidya & Mathias 2005;Virsodia et al, 2008).…”

Section: Structure Descriptionmentioning

confidence: 99%

3-[6-(4-Methoxyphenyl)-2-methylpyrimidin-4-yl]-2-(4-methylpiperazin-1-yl)quinoline

et al. 2018

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Section: Structure Descriptionmentioning

confidence: 99%

3-[6-(4-Methoxyphenyl)-2-methylpyrimidin-4-yl]-2-(4-methylpiperazin-1-yl)quinoline

et al. 2018

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“…Quinoline derivatives find importance owing to their wide occurrence in natural products and in biologically active compounds (Markees et al, 1970;Campbell et al, 1988;Kalluraya & Sreenivasa, 1998). Quinoline chalcone analogues have also attracted significant attention as a result of their bio-activity, e.g.…”

Section: Structure Descriptionmentioning

confidence: 99%

1-(4-Methoxyphenyl)-3-[2-(4-methylpiperazin-1-yl)quinolin-3-yl]prop-2-en-1-one

Sharma¹,

Desai²,

Sreenivasa³

et al. 2017

IUCr Data

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In the title molecule, C 24 H 25 N 3 O 2 , the piperazine ring adopts a chair conformation. The methoxyphenyl-substituted ring makes a dihedral angle of 6.79 (5) with the quinoline ring system. In the crystal, molecules are consolidated in the crystal packing by a combination of weak C-HÁ Á ÁN and C-HÁ Á ÁO interactions. -stacking interactions also occur. Structure descriptionQuinoline derivatives find importance owing to their wide occurrence in natural products and in biologically active compounds (Markees et al., 1970;Campbell et al., 1988;Kalluraya & Sreenivasa, 1998). Quinoline chalcone analogues have also attracted significant attention as a result of their bio-activity, e.g. anti-plasmodial, anti-microbial, anti-malarial and anti-cancer (Dimmock et al., 1999;Wu et al., 2006).In the molecule of the title compound, (Fig. 1), bond lengths are in normal ranges and are comparable with related structures (Kaiser et al., 2009;Prasath et al., 2010Prasath et al., , 2011. The piperazine ring adopts a chair conformation with best mirror plane passing through atoms C20 and C22 [asymmetry parameter ÁC s (C20) = 2/3] and the best twofold rotational axis bisecting the C22-C23 and C20-C21 bonds [asymmetry parameter ÁC 2 (C22-C23) = 0.43; Duax & Norton, 1975). The quinoline ring system is essentially planar with a maximum deviation of 0.0384 (1) Å for atom C17. The methoxyphenylsubstituted ring makes a dihedral angle of 6.79 (5) with the quinoline ring system. In the crystal, molecules are consolidated in the crystal packing by a combination of weak C-HÁ Á ÁN and C-HÁ Á ÁO interactions (Table 1, Fig. 2). The crystal structure also features -stacking interactions observed between the (C11-C13/C18/N1/C19) ring and the methoxyphenyl-substituted ring [centroid-centroid separation = 3.680 (1) Å , interplanar spacing = 3.350 Å and centroid shift = 1.52 Å ] and the benzene ring (C13-

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“…For background to and the biological activities of quinoline derivatives, see : Loh, Quah et al (2010a,b); Loh et al (2010); Sasaki et al (1998); Reux et al (2009); Morimoto et al (1991); Michael (1997); Markees et al (1970); Campbell et al (1988). For the hydrogen-bond motif, see: Bernstein et al (1995).…”

Section: Related Literaturementioning

confidence: 99%

2-Cyanoquinolin-1-ium nitrate

Loh¹,

Hemamalini²,

Fun³

2010

Acta Cryst E

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A proton is transferred from the nitric acid to the N atom of 2-cyanoquinoline during crystallization, resulting in the formation of the title salt, C10H7N2 +·NO3 −. The quinolinium ring system is approximately planar, with a maximum deviation of 0.013 (3) Å. In the crystal, a very asymmetric bifurcated N—H⋯(O,O) hydrogen bond to two O atoms of an adjacent nitrate anion occurs, generating an R 2 1(4) ring motif. C—H⋯O hydrogen bonds link the ions into sheets stacking along the a axis.

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Antiprotozoal 4-aryloxy-2-aminoquinolines and related compounds

Cited by 107 publications

References 0 publications

3-[6-(4-Methoxyphenyl)-2-methylpyrimidin-4-yl]-2-(4-methylpiperazin-1-yl)quinoline

3-[6-(4-Methoxyphenyl)-2-methylpyrimidin-4-yl]-2-(4-methylpiperazin-1-yl)quinoline

1-(4-Methoxyphenyl)-3-[2-(4-methylpiperazin-1-yl)quinolin-3-yl]prop-2-en-1-one

2-Cyanoquinolin-1-ium nitrate

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