Synthesis and Cytotoxic Activity of Indolo[2,3-a]Pyrrolo[3,4-c]Carbazole-5,7-Dione N-Glycosides Substituted on the Maleimide Nitrogen Atom

Эктова, Л. В.; Eremina, V. A.; Тихонова, Н. И.; Plikhtyak, I. L.; Medvedeva, L. A.; Yartseva, I. V.; Моисеева, Н. И.; Голубева, И. С.; Yavorskaya, I. P.; Будько, А. П.; Tarasova, O. I.; Пугачева, Р. Б.

doi:10.1007/s11094-020-02222-x

Cited by 7 publications

(4 citation statements)

References 3 publications

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“…PMR spectrum (DMSO-d 6 ), d, ppm: 2.85 (6H, s, N(CH 3 ) 2 ), 6.59 (1H, dd, J 3.3, 0.8 Hz), 7.08 (1H, dt, J 7.3, 0.8 Hz), 7.17 (1H, dt, J 9.1, 1.0 Hz), 7.29 (1H, d, J 6.9 Hz), 7.30 (1H, d, J 3.8 Hz), 7.59 (1H, d, J 7.7 Hz), 10.69 (1H, s, NH). 13 C NMR spectrum (DMSO-d 6 ), d, ppm: 39.7 (2C), 99.0, 102.5, 110.7, 119.9, 120.4, 122.0, 127.6, 131.6, 139.0, 143.6, 166.5 (C=O), 168.7 (C=O).…”

Section: -(Dimethylamino)-4-(1h-indol-1-yl)-1h-pyrrole-25dione (Xiib)mentioning

confidence: 99%

“…PMR spectrum (DMSO-d 6 ), d, ppm: 7.36 -7.47 (2H, m), 7.56 (1H, dd, J 6.9, 1.5 Hz), 8.20 (1H, dd, J 6.6, 1.9 Hz), 8.44 (1H, s), 10.11 (1H, s), 11.88 (1H, s). 13 C NMR spectrum (DMSO-d 6 ), d, ppm: 114.25, 121. 13, 121.86, 124.56, 124.99, 125.19, 125.77, 134.05, 136.15, 140.22, 165.3, 166.16, 186.73. 3-{3-[bis(1-Propyl-1H-indol-3-yl)methyl]-1H-indol-1-yl}-4-chloro-1H-pyrryole-2,5-dione (XVIII) was synthesized analogously to VIa using XVII (3.0 g, 5.2 mmol) and 1-propylindole (1.67 g, 10.5 mmol) to afford a product that was purified by column chromatography using EtOAc-petroleum-ether (gradient from 1:10 to 1:3) as eluent.…”

Section: -Amino-4-{3-[bis(1-propyl-1h-indol-3-yl)methyl]-1hindol-1-yl}-1h-pyrrole-25-dione (Via)mentioning

confidence: 99%

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Optimization of the Synthesis of New Antibacterial Compounds with Tris(1-Alkylindol-3-YL)Methylium Fragments

et al. 2021

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A new optimal synthetic scheme for new antibacterial compounds combining tris-(1-alkyindol-3-yl)methylium and 3-(indol-1-yl)maleimide in their structures was developed. The proposed method provided a significant increase in the product yield, reduced the labor intensiveness and number of steps, and used readily accessible starting reagents. A good yield was achieved for 3-(formylindol-1-yl)-4-chloromaleimide, a universal precursor enabling two-step syntheses of target tri(indolyl)methanes and production of an extensive library of analogous potentially active compounds from other 1-alkylindoles and various amines and thiols.

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Section: -(Dimethylamino)-4-(1h-indol-1-yl)-1h-pyrrole-25dione (Xiib)mentioning

confidence: 99%

Section: -Amino-4-{3-[bis(1-propyl-1h-indol-3-yl)methyl]-1hindol-1-yl}-1h-pyrrole-25-dione (Via)mentioning

confidence: 99%

Optimization of the Synthesis of New Antibacterial Compounds with Tris(1-Alkylindol-3-YL)Methylium Fragments

et al. 2021

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“…LCS-1269 has demonstrated high antitumor effectivity in experiments in vitro, showing significant antiproliferative activity against HCT-116 cells (Vartanian et al 2017;Ektova et al 2020).…”

Section: Introductionmentioning

confidence: 99%

“…In vivo LCS-1269 inhibits the growth of colon tumor AKATOL to 90% immediately after injection to experimental mice and about 60% during 26 days after the end of treatment; on cervical cancer RShM5, the immediate effect was 80% of tumor growth inhibition and kept on 50% level to the 15 the day of observation. Increase of life span reached 337% and 93% on experimental animals with Erlich tumor and leucosis Р388, accordingly (Yavorskaya et al 2016;Golubeva et al 2020;Ektova et al 2020).…”

Section: Introductionmentioning

confidence: 99%

Development and validation of HPLC method for analysis of indolocarbazole derivative LCS-1269

Shprakh¹,

Будько²,

Kozin³

et al. 2021

PHAR

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Indolocarbazole glycosidic derivative LCS-1269 with significant antiproliferative activity has been synthesized in N.N. Blokhin National Medical Research Center of Oncology. To control the quality of the substance, the chromatographic method of the assay was created and validated. The technique was carried out in a gradient mode using mobile phases consist of acetonitrile, trifluoroacetic acid and purified water. The specificity of the method was shown by checking of test solutions and the special solvent chromatograms. The method linearity was confirmed, and the parameters of linear dependence have been estimated, and the relationship was described by the equation: y = 49.23× – 35.51 with correlation coefficient 0.9998. The method’s precision was determined as the repeatability with a relative error of the mean 1.49% and was 2.433 ± 0.036. Was shown, that the results obtained in the intermediate precision estimation were not burdened with a systematic error. The detection limit and quantitation limit were calculated based on the linear relationship data as 3.15 μg/mL and 9.57 μg/mL, respectively. Sensitive HPLC method for LCS-1269 assay in substance has been developed and validated.

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Molecular-Genetic Basis of Gastrointestinal Stromal Tumor Personalized Therapy by Receptor Tyrosine Kinase Inhibitors (A Review)

et al. 2021

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Synthesis and Cytotoxic Activity of Indolo[2,3-a]Pyrrolo[3,4-c]Carbazole-5,7-Dione N-Glycosides Substituted on the Maleimide Nitrogen Atom

Cited by 7 publications

References 3 publications

Optimization of the Synthesis of New Antibacterial Compounds with Tris(1-Alkylindol-3-YL)Methylium Fragments

Optimization of the Synthesis of New Antibacterial Compounds with Tris(1-Alkylindol-3-YL)Methylium Fragments

Development and validation of HPLC method for analysis of indolocarbazole derivative LCS-1269

Molecular-Genetic Basis of Gastrointestinal Stromal Tumor Personalized Therapy by Receptor Tyrosine Kinase Inhibitors (A Review)

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