Synthesis and antimalarial activity of ethyl 3‐amino‐4‐oxo‐9‐(phenylsubstituted)thieno[2,3‐<i>b</i>]quinoline‐2‐carboxylate derivatives

Charris, Jaime; Barazarte, Arthur; Domínguez, José N.; Lobo, Gricela; Camacho, J.R.; Ferrer, Rosa; Gamboa, Neira; Rodrígues, Juan; Capparelli, Mario V.

doi:10.1002/jhet.5570440320

Cited by 11 publications

(4 citation statements)

References 16 publications

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“…In addition, active researches have been carried out on other types of biological activity in 4-quinolones. The following types of activity have been observed in a series of papers: Antiviral with respect to hepatitis B, C, and HIV viruses [3,4,24] and herpes viruses [3,37], antiallergic [3], antimalarial [68,109], antitubercular [36,39,110], immunomodulating [38], antihypoxic [25], antidiabetic [46]. 4-Quinolones have antithrombocytic [111] and positive cardiotonic activity [24].…”

Section: Biological Activity Of 4-quinolonesmentioning

confidence: 98%

“…Tricyclic compounds containing a 4-quinolone fragment [61], analogs of ofloxacin [63], and pentacyclic derivatives [66] can also be obtained by this method. At position 3 of the 4-quinolones there is usually a carboxyl or alkoxycarbonyl group [55,56,60,[63][64][65][66][67], although there may be a nitro group [59], a CN group [68], or H [58,69]. Moreover, the scheme can also used to obtain the quite rare 2-substituted 4-quinolones (carboxyl group [69], trifluoromethyl group [58]).…”

Section: Type Dmentioning

confidence: 99%

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The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

107

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Data on methods for the construction of the 4-quinolone skeleton and modification of the substituents around it are reviewed. The "structure-activity" relationships of 4-quinolones are examined with respect to antibacterial and antitumor activity.Keywords: 4-quinolones, biological activity. 4-Quinolones have been a subject of research for many scientific teams, and this is reflected in the numerous reviews and monographs devoted to various aspects of the subject. One of the early reviews [1] concerns aspects of the synthesis of individual representatives of the group of 4-quinolones and comparative characterization of their antimicrobial activity. Basic approaches to construction of the fluoroquinolone skeleton and also variation of the substituents at various positions of the ring were examined in the review [2]. The relationship between the structure and antibacterial activity is discussed in [3], and methods for the synthesis of polycyclic derivatives of 4-quinolones based on the annelation of rings to the various faces of the quinoline skeleton are discussed in the review [4]. The reviews [5, 6] were devoted to identification of the structural modifications of 4-quinolones responsible for their conversion from antibacterial agents to antitumor agents. The molecular and biological aspects of the antibacterial action of 4-quinolone-3-carboxylic acids are examined in [7], and issues concerned with the clinical application of 4-quinolones are discussed in the reviews [8][9][10][11][12] and in the monograph [13]. The synthesis and the "structure-activity" relationships of the bioisosteres of 4-quinolones -2-pyridones -are examined in the review [14].The aim of the present review was to classify existing methods for the synthesis not only of fluoroquinolones but also of any 4-quinolones, to demonstrate the effects of modification of the molecule at all positions, to summarize data on the various types of activity, and to examine the "structure-activity" relationship with respect to antibacterial and antitumor activity.

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Section: Biological Activity Of 4-quinolonesmentioning

confidence: 98%

Section: Type Dmentioning

confidence: 99%

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Boteva

Красных

2009

Chem Heterocycl Comp

107

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“…[3][4][5] more effective, antimalarial drugs, a number of quinoline, quinolone, pyrimidone, pyridopyrimidone, thiocromone, pyrazole and benzothiazine derivatives were synthesised, characterised and tested for antimalarial activity. [6][7][8][9][10][11][12][13][14][15] 3-Amino-7-chloro-9-phenyl-1,9H-pyrazolo- [4,3-b] Compounds 1 and 2 were synthesised as reported elsewhere. 16,17 Crystals suitable for X-ray diffraction were obtained by the slow evaporation of solution in EtOH.…”

mentioning

confidence: 99%

“…16,17 In vitro and in vivo assays of compounds 1 and 2 were tested following the procedure previously reported. 14 X-ray analysis Experimental crystallographic details are recorded in Table 3. Single crystals of size 0.78 0.58 0.08 mm 1 and 0.49 0.17 0.06 mm 2 were chosen for a single crystal in X-ray analysis.…”

mentioning

confidence: 99%

Crystal structures of two N-phenylated tricyclic benzothiazines with antimalarial activity

Barazarte

Gamboa

Rodrígues

et al. 2009

Journal of Chemical Research

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The crystal structures of two N-phenylated tricyclic benzothiazines were determined 3-amino-7-chloro-9-phenyl-1,9H-pyrazolo-[4,3-b] benzothiazine 4,4-dioxide, C 15 H 11 ClN 4 O 2 S crystallises in P2 1 /c with a = 11.436 (4)Å, b = 10.894 (3)Å, c = 11.858 (4)Å, = 95.297 (9)°, V = 1471.0 (8) Å 3 and Z = 4, while 2,4-diamino-8-chloro-10H-phenylpyrimido-[5,4b]benzothiazine 5,5-dioxide, C 16 H 12 ClN 5 O 2 S crystallises in P2 1 /c with a = 7.496 (2)Å, b = 17.728 (4)Å, c = 11.889 (2)Å, = 91.524 ( 5)°, V = 1579.4 (5)Å 3 and Z = 4. Both molecules are essentially planar, including the exocyclic groups. These compounds were promising as inhibitors of hemoglobin hydrolysis, however, their effect as inhibitors of -hematin formation was marginal. The most active compound to emerge from the in vitro and in vivo murine studies was the pyrimidobezothaizine, suggesting an antimalarial activity via inhibition of haemoglobin hydrolysis, but it was not as efficient as chloroquine.

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Synthesis and Antimalarial Activity of Ethyl 3‐Amino‐4‐oxo‐9‐(phenylsubstituted)thieno[2,3‐b]quinoline‐2‐carboxylate Derivatives.

Charris¹,

Barazarte²,

Domínguez³

et al. 2007

ChemInform

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Fused pyridine derivatives R 0450Synthesis and Antimalarial Activity of Ethyl 3-Amino-4-oxo-9-(phenylsubstituted)thieno[2,3-b]quinoline-2-carboxylate Derivatives. -A series of thieno[2,3-b]quinolone derivatives (III) is synthesized and evaluated for the ability to inhibit β-hematin formation, hemoglobin hydrolysis and in vivo efficacy in rodent Plasmodium berghei. The most active compound is (IIIb) suggesting an antimalarial activity via multiple mechanisms. -(CHARRIS*, J.; BARAZARTE, A.; DOMINGUEZ, J.; LOBO, G.; CAMACHO, J.; FERRER, R.; GAMBOA, N.; RODRIGUES, J.; CAPPARELLI, M. V.; J. Heterocycl. Chem. 44 (2007) 3, 639-643; Lab. Sint. Org., Fac. Farm., Univ. Cent. Venezuela, Caracas 1051, Venez.; Eng.) -H. Haber

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Synthesis and antimalarial activity of ethyl 3‐amino‐4‐oxo‐9‐(phenylsubstituted)thieno[2,3‐b]quinoline‐2‐carboxylate derivatives

Cited by 11 publications

References 16 publications

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

The methods of synthesis, modification, and biological activity of 4-quinolones (review)

Crystal structures of two N-phenylated tricyclic benzothiazines with antimalarial activity

Synthesis and Antimalarial Activity of Ethyl 3‐Amino‐4‐oxo‐9‐(phenylsubstituted)thieno[2,3‐b]quinoline‐2‐carboxylate Derivatives.

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