The potential use of 6-amino-5-methoxy(methyl)-2,3-dimethyl-and 6-amino-5-methoxy(methyl)-1,2,3-trimethyl-indoles in the synthesis of pyrrolo[2,3-f]quinolines

Yamashkin, S. A.; Oreshkina, E. A.; Romanova, I. S.; Yurovskaya, M. A.

doi:10.1007/s10593-006-0051-0

Cited by 3 publications

(1 citation statement)

References 5 publications

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“…Of particular interest are aminoindoles with an aminogroup in the benzene part of the molecule. These compounds, like any aromatic amines can give various kinds of derivatives with an aminogroup (Yamashkin et al 2006;Alyamkina et al 2017). The authors of the present paper carried out the studies on the interaction of β-dioxo compounds with substituted aminoindoles, with different positions of the amino group in the benzene ring.…”

Section: Introductionmentioning

confidence: 99%

A new group of compounds derived from 4-, 5-, 6- and 7-aminoindoles with antimicrobial activity

Степаненко¹,

Yamashkin²,

Kostina³

et al. 2018

RRP

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Introduction. The problem of antibiotic resistance of microorganisms is becoming more urgent in the twenty-first century. Microorganisms possess an evolutionary adaptive capacity. Non-adherence to the basic principles of rational antibiotic therapy leads to menacing consequences. More and more pathogenic microbes are becoming resistant to two or more antibiotics. The search for new compounds with antimicrobial activity is one of the principles for overcoming the antibiotic resistance of microorganisms. Materials and methods. Eighteen test-strains of microorganisms and more than 2000 clinical strains of microorganisms, representating the families Micrococcaceae, Streptococcaceae, Enterobacteriaceae, Moraxellaceae, Pseudomonadaceae, Sphingomonadaceae, Xanthomonadaceae were studied for sensitivity to the compounds derived from 4-, 5-, 6- and 7-aminoindoles. A method of serial dilutions to determine the minimal inhibitory concentration (MIC) of the compounds under study was used in the study, as well as a disc diffusion method. Results and discussion. Sensitivity of the test-strains and of clinical strains of microorganisms to the resulting compounds was studied. The compounds based on substituted 4-, 5-, 6-, 7-aminoindoles showed different activity against the test strains and experimental strains of microorganisms in vitro. It was found that the marked antibacterial activity was exhibited by the compounds containing a trifluoromethyl group. The most significant activity was noted in amides and pyrroloquinolones based on 4-aminoindole, 6-aminoindole and 7-aminoindole.The most effective compounds with laboratory codes 5D, 7D, 39D, S3, HD, 4D showed a pronounced antibacterial activity. Conclusion. Antimicrobial activity of the substituted amides and pyrroloquinolines on the basis of 4-, 5-, 6-, 7-aminoindoles was etermined in our study, as well as the spectra of their action against Gram-positive and Gram-negative microorganisms, which are causative agents of non-specific and certain specific human infectious diseases. Moreover, we evaluated the synthetic potentials of the substituted 4-, 5-, 6-, 7-aminoindoles as the starting compounds for synthesizing a series of indolylamides and pyrroloquinolines. Also, the prospects for targeted synthesis of biologically active compounds based on indole-type aromatic amines were determined.

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Section: Introductionmentioning

confidence: 99%

A new group of compounds derived from 4-, 5-, 6- and 7-aminoindoles with antimicrobial activity

Степаненко¹,

Yamashkin²,

Kostina³

et al. 2018

RRP

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The Potential Use of 6‐Amino‐5‐methoxy(methyl)‐2,3‐dimethyl‐ and 6‐Amino‐5‐methoxy(methyl)‐1,2,3‐trimethylindoles in the Synthesis of Pyrrolo[2,3‐f]quinolines.

et al. 2006

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Fused pyridine derivatives R 0450The Potential Use of 6-Amino-5-methoxy(methyl)-2,3-dimethyl-and 6-Amino-5-methoxy(methyl)-1,2,3-trimethylindoles in the Synthesis of Pyrrolo[2,3-f]quinolines. -It is found that all of the aminoindoles investigated readily undergo condensation reactions with β-dicarbonyl compounds to form the corresponding enamines. However, the possible subsequent cyclization to give the target pyrrolo[2,3-f]quinolines is found only for the condensation product of 6-amino-2,3,5-trimethylindole (IV) with 4,4,4-trifluoroacetoacetate (II). -(YAMASHKIN, S. A.; ORESHKINA, E. A.; ROMANOVA, I. S.; YUROVSKAYA, M. A.; Chem. Heterocycl. Compd. (N. Y.) 42 (2006) 1, 86-91; Ogarev Mordovian State Univ., Saransk 430000, Russia; Eng.) -M. Kowall 41-152

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An impact of 1H-indol-4-, -5-, -6-, -7-ylamines-substituted compounds on the microbial cell genetic apparatus

Масейкина

Степаненко

Ямашкин

et al. 2020

Russian Journal of Infection and Immunity

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The study of new antimicrobial compounds includes determining the mechanism of their effect on the microbial cell. As a rule, the effect of most modern synthetic antimicrobials is associated either with the suppression of DNA synthesis, or with the suppression of bacterial protein synthesis at the level of translation or transcription.There are sensitive and simple methods for screening and monitoring the potential genotoxic activity of a wide range of natural and synthetic compounds. To date, the Ames test has been widely used, based on the sensitivity of Salmonella strains to carcinogenic chemicals, although some compounds that cause Ames negative reactions could actually be carcinogenic to animals.Similarly, the SOS chromotest is an SOS transcriptional analysis that can evaluate DNA damage caused by chemical and physical mutagens. It measures the expression of a reporter gene (β-galactosidase). The β-galactosidase enzyme processes ortho-nitrophenyl galactopyranoside to form a yellow compound detected at 420 nm. Then, the induction of β-galactosidase normalizes the activity of alkaline phosphatase, an enzyme expressed constitutively by Escherichia coli. SOS chromotest is also widely used for genotoxicological studies. The answer is quick (several hours) and does not require the survival of the test strain. Dose response curves for various chemicals include a linear region. The slope of this area is taken as a measure of SOS induction.Therefore, an SOS chromotest was selected for the study, which allows one to identify the DNA-mediated effect of the studied compounds.The aim of the work was to evaluate the SOS-inducing activity of antimicrobial compounds based on substituted 1H-indol-4-, 5-, 6-, 7-ylamines.The strain Escherichia coli PQ 37 with the genotype F-thr leu his-4 pyrD thi galE lacΔU169 srl300 :: Th10 rpoB rpsL uvrA rfa trp :: Mis + sfi A :: Mud (Ar, lac) cts, Due to the presence of sfi A genes :: lac Z, lacZ β-galactosidase gene expression in strain PQ 37 is controlled by the promoter of the sfiA gene, one of the components of the E. coli SOS regulon. The indicator of the SOS-inducing activity of the studied compounds in the SOS chromotest is the activity of β-galactosidase, which evaluates the activity of active microorganisms - alkaline phosphatase, which also allows you to control the toxic effect of the studied compounds on bacterial cells.The results showed that 4,4,4-trifluoro-N-(6-methoxy-1,2,3-trimethyl-1H-indol-5-yl)-3-oxobutanamide (1), 4,4,4-trifluoro-N-(6-methyl-2-phenyl-1H-indol-5-yl)-3-oxobutanamide (2) and N-(1,5-dimethyl-2-phenyl-1H-indol-6-yl)-4,4,4-trifluoro-3-oxobutanamide (3) does not possess SOS-inducing activity in the studied concentrations. 4-Hydroxy-8-phenyl-4-(trifluoromethyl)-1,3,4,7-tetrahydro-2H-pyrrolo [2,3-h] -quinolin-2-one (4), 9-hydroxy-5-methyl-2-phenyl-9-(trifluoromethyl)-1,6,8,9-tetrahydro-7Н-pyrrolo-[2,3-f]quinolin-7-one (5), 6-hydroxy-2,3-dimethyl-6-(trifluoromethyl)-1,6,7,9-tetrahydro-8H-pyrrolo[3,2-h]quinolin-8-one (6) and 1,2,3,9-tetramethyl-6-(trifluoromethyl)-1,9-dihydro-8H-pyrrolo [3,2-h]quinolin-8-one (7) showed dose-dependent SOS-inducing activity in bactericidal concentrations. The obtained research results allowed us to identify compounds 4, 5, 6, 7, the mechanism of action of which includes exposure to DNA of a microbial cell.

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The potential use of 6-amino-5-methoxy(methyl)-2,3-dimethyl-and 6-amino-5-methoxy(methyl)-1,2,3-trimethyl-indoles in the synthesis of pyrrolo[2,3-f]quinolines

Cited by 3 publications

References 5 publications

A new group of compounds derived from 4-, 5-, 6- and 7-aminoindoles with antimicrobial activity

A new group of compounds derived from 4-, 5-, 6- and 7-aminoindoles with antimicrobial activity

The Potential Use of 6‐Amino‐5‐methoxy(methyl)‐2,3‐dimethyl‐ and 6‐Amino‐5‐methoxy(methyl)‐1,2,3‐trimethylindoles in the Synthesis of Pyrrolo[2,3‐f]quinolines.

An impact of 1H-indol-4-, -5-, -6-, -7-ylamines-substituted compounds on the microbial cell genetic apparatus

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