4-Phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one

Sergey A. Smolnikov; Ekaterina V. Gorgopina; Vera R. Lezhnyova; Gwyneth En Tian Ong; Wai Keung Chui; Anton V. Dolzhenko

doi:10.3390/M970

4-Phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one

Sergey A. Smolnikov, Ekaterina V. Gorgopina, Vera R. Lezhnyova, Gwyneth En Tian Ong, Wai Keung Chui, Anton V. Dolzhenko

Malaysia Sch of Pharmacy

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

7 Citations (Scopus)

Abstract

Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2- phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo [1,5-a][1,3,5]triazine-7(6H)-one (3), prepared by the double ring closure of pyrazole and triazine rings upon the treatment of 1-cyanoacetyl-4-benzoylthiosemicarbazide (2) with alkali. The antiproliferative activity of 4 against human lung cancer (A549) and human breast cancer (MDA-MB231) cell lines was investigated. Compound 4 was found to be more active against lung cancer cells than breast cancer cells.

Original language	English
Article number	M970
Number of pages	5
Journal	Molbank
Volume	2017
Issue number	4
DOIs	https://doi.org/10.3390/M970
Publication status	Published - 15 Dec 2017

Keywords

Anticancer activity
Purine isostere
Pyrazole
Pyrazolotriazine
Triazine

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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title = "4-Phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one",

abstract = "Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2- phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo [1,5-a][1,3,5]triazine-7(6H)-one (3), prepared by the double ring closure of pyrazole and triazine rings upon the treatment of 1-cyanoacetyl-4-benzoylthiosemicarbazide (2) with alkali. The antiproliferative activity of 4 against human lung cancer (A549) and human breast cancer (MDA-MB231) cell lines was investigated. Compound 4 was found to be more active against lung cancer cells than breast cancer cells.",

keywords = "Anticancer activity, Purine isostere, Pyrazole, Pyrazolotriazine, Triazine",

author = "Smolnikov, {Sergey A.} and Gorgopina, {Ekaterina V.} and Lezhnyova, {Vera R.} and Ong, {Gwyneth En Tian} and Chui, {Wai Keung} and Dolzhenko, {Anton V.}",

note = "Funding Information: Acknowledgments: This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme (FRGS). Funding Information: This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme (FRGS). Publisher Copyright: {\textcopyright} 2017 by the authors. Licensee MDPI, Basel, Switzerland. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.",

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doi = "10.3390/M970",

language = "English",

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T1 - 4-Phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one

AU - Smolnikov, Sergey A.

AU - Gorgopina, Ekaterina V.

AU - Lezhnyova, Vera R.

AU - Ong, Gwyneth En Tian

AU - Chui, Wai Keung

AU - Dolzhenko, Anton V.

N1 - Funding Information: Acknowledgments: This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme (FRGS). Funding Information: This work is supported by the Ministry of Higher Education, Malaysia under Fundamental Research Grant Scheme (FRGS). Publisher Copyright: © 2017 by the authors. Licensee MDPI, Basel, Switzerland. Copyright: Copyright 2018 Elsevier B.V., All rights reserved.

PY - 2017/12/15

Y1 - 2017/12/15

N2 - Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2- phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo [1,5-a][1,3,5]triazine-7(6H)-one (3), prepared by the double ring closure of pyrazole and triazine rings upon the treatment of 1-cyanoacetyl-4-benzoylthiosemicarbazide (2) with alkali. The antiproliferative activity of 4 against human lung cancer (A549) and human breast cancer (MDA-MB231) cell lines was investigated. Compound 4 was found to be more active against lung cancer cells than breast cancer cells.

AB - Exploring the pharmacologically important pyrazolo[1,5-a][1,3,5]triazin-7(6H)-one scaffold for the construction of new bioactive compounds, we developed a synthesis of 4-phenethylthio-2- phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one (4) via S-alkylation of 2-phenyl-4-thioxopyrazolo [1,5-a][1,3,5]triazine-7(6H)-one (3), prepared by the double ring closure of pyrazole and triazine rings upon the treatment of 1-cyanoacetyl-4-benzoylthiosemicarbazide (2) with alkali. The antiproliferative activity of 4 against human lung cancer (A549) and human breast cancer (MDA-MB231) cell lines was investigated. Compound 4 was found to be more active against lung cancer cells than breast cancer cells.

KW - Anticancer activity

KW - Purine isostere

KW - Pyrazole

KW - Pyrazolotriazine

KW - Triazine

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4-Phenethylthio-2-phenylpyrazolo[1,5-a][1,3,5]triazin-7(6H)-one

Abstract

Keywords

UN SDGs

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