Synthesis and antinephritic activities of quinoline-3-carboxamides and related compounds

Tsuji, Kiyoshi; Spears, Glen W.; Nakamura, Katsuya; Tojo, Takashi; Seki, Nobuo; Sugiyama, Aiko; Matsuo, Masaaki

doi:10.1016/s0960-894x(01)00671-0

Cited by 27 publications

(22 citation statements)

References 17 publications

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“…The known isatoic anhydride 3 [6] was converted to the amine 8a (Scheme 1) in nearly quantitative yield with catalytic sodium ethoxide in refluxing ethanol for 30 minutes [7]. The preparation of acid 9a has been previously described by us [8] and proceeds in 93% yield by hydrolysis of 4 with aqueous sodium hydroxide in methanol.…”

Section: Jul-aug 2002 799mentioning

confidence: 99%

An efficient synthesis of a class of novel N‐Alkyl‐N‐aryl‐4‐hydroxy‐1‐methyl‐2‐oxo‐1,2‐dihydro‐3‐quinolinecarbothioamides

Spears

Tsuji

Tojo

et al. 2002

Journal of Heterocyclic Chem

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Section: Jul-aug 2002 799mentioning

confidence: 99%

An efficient synthesis of a class of novel N‐Alkyl‐N‐aryl‐4‐hydroxy‐1‐methyl‐2‐oxo‐1,2‐dihydro‐3‐quinolinecarbothioamides

Spears

Tsuji

Tojo

et al. 2002

Journal of Heterocyclic Chem

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“…antimalarial, 2 antibacterial, 3,4 antitubuerculosis, 5 anticancer activity, 6,7 analgesic activity, 8 anti-inflammatory activity, 8 anti-rheumatic, 9 antitinephritic, 10 or in treating alzheimer's disease (AD).…”

Section: Introductionmentioning

confidence: 99%

Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate

Fathala¹,

Pazdera²

2017

Arkivoc

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A series of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates 7a-f has been developed by the direct condensation of ethyl [4-hydroxy-2-oxo--1-phenyl-1,2-dihydro-3-quinoline] carboxylate 4 with amino acid ester hydrochloride in the presence of triethylamine. The quinoline amino acid esters 7a-f were the key intermediate for the preparation of a series of methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino)alkanamido] alkanoate 10-13(a-f) via azide coupling method with amino acid ester.

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“…In molecule A the C (7) -C (8) bond at 1.414(7) Å is lengthened in comparison with its mean value of 1.326 Å [17]. This might be explained by the significant contribution to the geometry of the molecule of a …”

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confidence: 99%

“…109.0 Analysis of the bond lengths in molecule B (bonds O (1) -C (9) at 1.249 (7) and C (7) -C (8) at 1.404(8) Å were lengthened (mean values 1.210 and 1.326 Å) but bonds O (2) -C (7) at 1.304 (6) and C (8) -C (9) 1.432(8) Å were shortened (mean values 1.333 and 1.464 Å)] permitted the suggestion that the geometry of the ester 1 molecule is described as a resonance hybrid of two canonical structures 1 ↔ 1a (Scheme 1). This was also confirmed by the fairly weak character of the intramolecular hydrogen bond in the B molecule O (2) -H (20) …”

mentioning

confidence: 99%

4-hydroxy-2-quinolones. 94. Improved synthesis and structure of 1-hydroxy-3-oxo-5,6-dihydro-3h-pyrrolo[3,2,1-i,j]-quinoline-2-carboxylic acid ethyl ester

Украинец

Сидоренко

Gorokhova

et al. 2006

Chem Heterocycl Compd

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A modified method is proposed for preparation and purification, and the special features of the spatial structure have been studied for the ethyl ester Keywords: heterocyclic derivatives of tricarbonylmethane, ethyl esters of 4-hydroxy-2-oxoquinoline-3-carboxylic acids, X-ray structural analysis.Esters of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids display interesting pharmacological properties [2][3][4] and in addition are widely used for obtaining the corresponding alkyl, aryl and heterylamides, and hydrazides. The various hetaryl-substituted quinol-2-ones possess antithyroidal [5], anti-inflammatory [6], local anesthetic [7], antinephritic [8], antitubercular [9], herbicidal [10], antitumor [11], and other forms of biological activity.Several methods of synthesizing such compounds are known today. However, only some of them are used, mostly for preparative purposes, and assume the interaction of alkylanthranilates [12], isatoic acid anhydrides [13,14], or 2-carbalkoxyphenyl isocyanates [15] with derivatives of malonic acid. Subsequent heterocyclization catalyzed by bases leads to esters of 4-hydroxy-2-oxo-1,2-dihydroquinoline-3-carboxylic acids. On the whole these methods have been well studied, give excellent yields, and are limited only by the availability of the appropriate anthranilic acids.Comparatively recently a new variant has been proposed for assembling 4-hydroxy-3-carbalkoxy-2-oxoquinoline systems, based on the interaction of trialkyl methanetricarboxylates with N-substituted anilines, including cyclic derivatives. As an example may be given the synthesis of the ethyl ester of 1-hydroxy-3-oxo-5,6-dihydro-3H-pyrrolo[3,2,1-i,j]quinoline-2-carboxylic acid (1). This includes the condensation of indoline 2 with the triethyl ester of methanetricarboxylic acid (3) [16]. The advantage of this method is that it is one stage, and also it is possible in certain cases to synthesize successfully desired compounds difficult to obtain by other methods. Regrettably, it is not devoid of drawbacks, the most important of which is the formation of side products, acyclic methanetri-N-R-carboxamides. For the suppression of this undesirable reaction a double [16], and sometimes a triple [14], excess of triethyl methanetricarboxylate is used, which reduces the overall

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Synthesis and antinephritic activities of quinoline-3-carboxamides and related compounds

Cited by 27 publications

References 17 publications

An efficient synthesis of a class of novel N‐Alkyl‐N‐aryl‐4‐hydroxy‐1‐methyl‐2‐oxo‐1,2‐dihydro‐3‐quinolinecarbothioamides

An efficient synthesis of a class of novel N‐Alkyl‐N‐aryl‐4‐hydroxy‐1‐methyl‐2‐oxo‐1,2‐dihydro‐3‐quinolinecarbothioamides

Synthesis of methyl 2-[(1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonylamino] alkanoates and methyl 2-[2-((1,2-dihydro-4-hydroxy-2-oxo-1-phenylquinolin-3-yl)carbonyl-amino)alkanamido] alkanoate

4-hydroxy-2-quinolones. 94. Improved synthesis and structure of 1-hydroxy-3-oxo-5,6-dihydro-3h-pyrrolo[3,2,1-i,j]-quinoline-2-carboxylic acid ethyl ester

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