Synthesis and Study of Some Properties of New Tetrazole-Containing Derivatives of Morpholin-4-yl-1,3,5-triazine and 4-Methylpiperidin-1-yl-1,3,5-triazine

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Synthesis and Study of Some Properties of New Tetrazole-Containing Derivatives of Morpholin-4-yl-1,3,5-triazine and 4-Methylpiperidin-1-yl-1,3,5-triazine. / Mikolaichuk, O. V.; Protas, A. V.; Popova, E. A.; Lutsev, M. D.; Smirnov, E. Yu.; Golotin, V. A.; Ostrovskii, V. A.; Kornyakov, I. V.; Semenov, K. N.; Sharoyko, V. V.; Molchanov, O. E.; Maistrenko, D. N.

In: Russian Journal of General Chemistry, Vol. 93, No. 5, 01.05.2023, p. 1050–1063.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{33c6b2e28bf24600bdb2ffe39adfa78e,

title = "Synthesis and Study of Some Properties of New Tetrazole-Containing Derivatives of Morpholin-4-yl-1,3,5-triazine and 4-Methylpiperidin-1-yl-1,3,5-triazine",

abstract = "Abstract: New tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine were synthesized. The cytotoxic activity of the obtained compounds against human liver Huh-7 and human lung A549 tumor cell lines was tested by MTT assay. It was demonstrated that these substances do not show pronounced cytotoxic effects. The most significant antitumor activity was exhibited by 1,3,5-triazine containing a 5-phenyltetrazol-2-ylacetohydrazide moiety and a 4-methylpiperidine ring as substituents, as well as by 1,3,5-triazine bearing a 5-methyl-1H-tetrazol-1-ylacetohydrazide moiety and two morpholine rings. For these compounds, the interaction with DNA was studied by UV spectroscopy. Also, for N'-(4,6-dimorpholino-1,3,5-triazin-2-yl)-2-(5-methyl-1H-tetrazol-1-yl)acetohydrazide, the DNA binding constant was determined (K bin 9.02×104 M−1), and the ability to inhibit the tyrosine kinase domain of the cell-surface receptors was evaluated. It was shown that the studied tetrazole-containing 1,3,5-triazine derivatives do not exhibit antioxidant activity against NO radicals and do not cause photoinduced hemolysis.",

keywords = "1,3,5-triazine, 5-aryltetrazoles, 5-methyl-1H-tetrazol-1-ylacetohydrazide, 5-phenyl-2H-tetrazol-2-ylacetohydrazide, cytotoxic activity, inhibitory activity",

author = "Mikolaichuk, {O. V.} and Protas, {A. V.} and Popova, {E. A.} and Lutsev, {M. D.} and Smirnov, {E. Yu.} and Golotin, {V. A.} and Ostrovskii, {V. A.} and Kornyakov, {I. V.} and Semenov, {K. N.} and Sharoyko, {V. V.} and Molchanov, {O. E.} and Maistrenko, {D. N.}",

year = "2023",

month = may,

day = "1",

doi = "10.1134/S1070363223050055",

language = "English",

volume = "93",

pages = "1050–1063",

journal = "Russian Journal of General Chemistry",

issn = "1070-3632",

publisher = "МАИК {"}Наука/Интерпериодика{"}",

number = "5",

}

RIS

TY - JOUR

T1 - Synthesis and Study of Some Properties of New Tetrazole-Containing Derivatives of Morpholin-4-yl-1,3,5-triazine and 4-Methylpiperidin-1-yl-1,3,5-triazine

AU - Mikolaichuk, O. V.

AU - Protas, A. V.

AU - Popova, E. A.

AU - Lutsev, M. D.

AU - Smirnov, E. Yu.

AU - Golotin, V. A.

AU - Ostrovskii, V. A.

AU - Kornyakov, I. V.

AU - Semenov, K. N.

AU - Sharoyko, V. V.

AU - Molchanov, O. E.

AU - Maistrenko, D. N.

PY - 2023/5/1

Y1 - 2023/5/1

N2 - Abstract: New tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine were synthesized. The cytotoxic activity of the obtained compounds against human liver Huh-7 and human lung A549 tumor cell lines was tested by MTT assay. It was demonstrated that these substances do not show pronounced cytotoxic effects. The most significant antitumor activity was exhibited by 1,3,5-triazine containing a 5-phenyltetrazol-2-ylacetohydrazide moiety and a 4-methylpiperidine ring as substituents, as well as by 1,3,5-triazine bearing a 5-methyl-1H-tetrazol-1-ylacetohydrazide moiety and two morpholine rings. For these compounds, the interaction with DNA was studied by UV spectroscopy. Also, for N'-(4,6-dimorpholino-1,3,5-triazin-2-yl)-2-(5-methyl-1H-tetrazol-1-yl)acetohydrazide, the DNA binding constant was determined (K bin 9.02×104 M−1), and the ability to inhibit the tyrosine kinase domain of the cell-surface receptors was evaluated. It was shown that the studied tetrazole-containing 1,3,5-triazine derivatives do not exhibit antioxidant activity against NO radicals and do not cause photoinduced hemolysis.

AB - Abstract: New tetrazole-containing derivatives of morpholin-4-yl-1,3,5-triazine and 4-methylpiperidin-1-yl-1,3,5-triazine were synthesized. The cytotoxic activity of the obtained compounds against human liver Huh-7 and human lung A549 tumor cell lines was tested by MTT assay. It was demonstrated that these substances do not show pronounced cytotoxic effects. The most significant antitumor activity was exhibited by 1,3,5-triazine containing a 5-phenyltetrazol-2-ylacetohydrazide moiety and a 4-methylpiperidine ring as substituents, as well as by 1,3,5-triazine bearing a 5-methyl-1H-tetrazol-1-ylacetohydrazide moiety and two morpholine rings. For these compounds, the interaction with DNA was studied by UV spectroscopy. Also, for N'-(4,6-dimorpholino-1,3,5-triazin-2-yl)-2-(5-methyl-1H-tetrazol-1-yl)acetohydrazide, the DNA binding constant was determined (K bin 9.02×104 M−1), and the ability to inhibit the tyrosine kinase domain of the cell-surface receptors was evaluated. It was shown that the studied tetrazole-containing 1,3,5-triazine derivatives do not exhibit antioxidant activity against NO radicals and do not cause photoinduced hemolysis.

KW - 1,3,5-triazine

KW - 5-aryltetrazoles

KW - 5-methyl-1H-tetrazol-1-ylacetohydrazide

KW - 5-phenyl-2H-tetrazol-2-ylacetohydrazide

KW - cytotoxic activity

KW - inhibitory activity

UR - https://www.mendeley.com/catalogue/8eb78c6e-d1c9-3e25-ab11-2b910f16be5c/

U2 - 10.1134/S1070363223050055

DO - 10.1134/S1070363223050055

M3 - Article

VL - 93

SP - 1050

EP - 1063

JO - Russian Journal of General Chemistry

JF - Russian Journal of General Chemistry

SN - 1070-3632

IS - 5

ER -

ID: 113806400