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4-Diazo and 4-(Triaz-1-en-1-yl)-1H-pyrrole-2-carboxylates as Agents Inducing Apoptosis. / Галенко, Екатерина; Галенко, Алексей Викторович; Новиков, Михаил Сергеевич; Хлебников, Александр Феодосиевич; Kudryavtsev, I.V.; Terpilowski, Maxim A.; Serebriakova, M.K.; Trulioff, A.S.; Goncharov, Nikolay V.

In: ChemistrySelect, Vol. 2, No. 25, 2017, p. 7508-7513.

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@article{1e0fd407a0464e0f98741ba3c6e1f561,
title = "4-Diazo and 4-(Triaz-1-en-1-yl)-1H-pyrrole-2-carboxylates as Agents Inducing Apoptosis",
abstract = "New beta-diazopyrrole and -triazenylpyrrole derivatives were synthesized from isoxazoles and pyridinium salts in two and three steps, respectively. The apoptotic/necrotic difference for these compounds was estimated on THP-1 cell line. The most effective of the panel is methyl 3-diazo-2-(2,4-dimethylphenyl)-4-phenyl-3H-pyrrole-5-carboxylate which demonstrated cytotoxic activity from the lowest concentration of 3.3 mu M with a steep rise of the apoptotic effect and the largest apoptotic/necrotic difference within the range of 3.3 to 33 mu M. Moreover, this diazopyrrole showed the highest sum total of apoptotic and necrotic AUCs within the same low range of concentrations. Methyl 2-(4-bromophenyl)-3-diazo-4-(3-methoxyphenyl)-3H-pyrrole-5-carboxylate and methyl 5-(4-bromophenyl)-3-(3-methoxyphenyl)-4-(piperidin-1-yl/morpholin-4-yldiazenyl)-1H-pyrrole-2-carboxylates were found to be quite promising compounds which deserve further cytophysiological and mechanistic research using different cell lines.",
keywords = "apoptosis, cytotoxicity, diazo compounds, heterocycles, BIOLOGICAL-ACTIVITY, CANCER-CELLS, INDEX, 3-TRIAZENOPYRROLES, TRIAZENOINDAZOLES, CAMPTOTHECIN, RESISTANCE",
author = "Екатерина Галенко and Галенко, {Алексей Викторович} and Новиков, {Михаил Сергеевич} and Хлебников, {Александр Феодосиевич} and I.V. Kudryavtsev and Terpilowski, {Maxim A.} and M.K. Serebriakova and A.S. Trulioff and Goncharov, {Nikolay V.}",
year = "2017",
doi = "10.1002/slct.201701538",
language = "Английский",
volume = "2",
pages = "7508--7513",
journal = "ChemistrySelect",
issn = "2365-6549",
publisher = "Wiley-Blackwell",
number = "25",

}

RIS

TY - JOUR

T1 - 4-Diazo and 4-(Triaz-1-en-1-yl)-1H-pyrrole-2-carboxylates as Agents Inducing Apoptosis

AU - Галенко, Екатерина

AU - Галенко, Алексей Викторович

AU - Новиков, Михаил Сергеевич

AU - Хлебников, Александр Феодосиевич

AU - Kudryavtsev, I.V.

AU - Terpilowski, Maxim A.

AU - Serebriakova, M.K.

AU - Trulioff, A.S.

AU - Goncharov, Nikolay V.

PY - 2017

Y1 - 2017

N2 - New beta-diazopyrrole and -triazenylpyrrole derivatives were synthesized from isoxazoles and pyridinium salts in two and three steps, respectively. The apoptotic/necrotic difference for these compounds was estimated on THP-1 cell line. The most effective of the panel is methyl 3-diazo-2-(2,4-dimethylphenyl)-4-phenyl-3H-pyrrole-5-carboxylate which demonstrated cytotoxic activity from the lowest concentration of 3.3 mu M with a steep rise of the apoptotic effect and the largest apoptotic/necrotic difference within the range of 3.3 to 33 mu M. Moreover, this diazopyrrole showed the highest sum total of apoptotic and necrotic AUCs within the same low range of concentrations. Methyl 2-(4-bromophenyl)-3-diazo-4-(3-methoxyphenyl)-3H-pyrrole-5-carboxylate and methyl 5-(4-bromophenyl)-3-(3-methoxyphenyl)-4-(piperidin-1-yl/morpholin-4-yldiazenyl)-1H-pyrrole-2-carboxylates were found to be quite promising compounds which deserve further cytophysiological and mechanistic research using different cell lines.

AB - New beta-diazopyrrole and -triazenylpyrrole derivatives were synthesized from isoxazoles and pyridinium salts in two and three steps, respectively. The apoptotic/necrotic difference for these compounds was estimated on THP-1 cell line. The most effective of the panel is methyl 3-diazo-2-(2,4-dimethylphenyl)-4-phenyl-3H-pyrrole-5-carboxylate which demonstrated cytotoxic activity from the lowest concentration of 3.3 mu M with a steep rise of the apoptotic effect and the largest apoptotic/necrotic difference within the range of 3.3 to 33 mu M. Moreover, this diazopyrrole showed the highest sum total of apoptotic and necrotic AUCs within the same low range of concentrations. Methyl 2-(4-bromophenyl)-3-diazo-4-(3-methoxyphenyl)-3H-pyrrole-5-carboxylate and methyl 5-(4-bromophenyl)-3-(3-methoxyphenyl)-4-(piperidin-1-yl/morpholin-4-yldiazenyl)-1H-pyrrole-2-carboxylates were found to be quite promising compounds which deserve further cytophysiological and mechanistic research using different cell lines.

KW - apoptosis

KW - cytotoxicity

KW - diazo compounds

KW - heterocycles

KW - BIOLOGICAL-ACTIVITY

KW - CANCER-CELLS

KW - INDEX

KW - 3-TRIAZENOPYRROLES

KW - TRIAZENOINDAZOLES

KW - CAMPTOTHECIN

KW - RESISTANCE

U2 - 10.1002/slct.201701538

DO - 10.1002/slct.201701538

M3 - статья

VL - 2

SP - 7508

EP - 7513

JO - ChemistrySelect

JF - ChemistrySelect

SN - 2365-6549

IS - 25

ER -

ID: 13392828