Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones

Dmytro Havrylyuk; Borys Zimenkovsky; Olexandr Vasylenko; Craig W. Day; Donald F. Smee; Philippe Grellier; Roman Lesyk

doi:10.1016/j.ejmech.2013.05.044

Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones

Dmytro Havrylyuk, Borys Zimenkovsky, Olexandr Vasylenko, Craig W. Day, Donald F. Smee, Philippe Grellier, Roman Lesyk

Chemistry

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

78 Scopus citations

Abstract

A series of novel 5-pyrazoline substituted 4-thiazolidinones have been synthesized. Target compounds were evaluated for their anticancer activity in vitro within DTP NCI protocol. Among the tested compounds, the derivatives 4d and 4f were found to be the most active, which demonstrated certain sensitivity profile toward the leukemia subpanel cell lines with GI₅₀ value ranges of 2.12-4.58 μM (4d) and 1.64-3.20 μM (4f). The screening of antitrypanosomal and antiviral activities of 5-(3-naphthalen-2-yl-5-aryl-4,5-dihydropyrazol-1-yl)-thiazolidine-2,4-diones was carried out with the promising influence of the mentioned compounds on Trypanosoma brucei, but minimal effect on SARS coronavirus and influenza types A and B viruses.

Original language	English
Pages (from-to)	228-237
Number of pages	10
Journal	European Journal of Medicinal Chemistry
Volume	66
DOIs	https://doi.org/10.1016/j.ejmech.2013.05.044
State	Published - Aug 2013

Bibliographical note

Funding Information:
We are grateful to Dr. V.L. Narayanan from Drug Synthesis and Chemistry Branch, National Cancer Institute, Bethesda, MD, USA, for in vitro evaluation of anticancer activity. Evaluations of compounds for antiviral activity were supported by funds from contract N01-AI-15435 from the Virology Branch, Division of Microbiology and Infectious Diseases, National Institute of Allergy and Infectious Diseases, National Institutes of Health , Bethesda, MD, USA.

Publisher Copyright:
© 2013 Elsevier Masson SAS.

Keywords

4-Thiazolidinones
Anticancer activity
Antitrypanosomal activity
Antiviral activity
Pyrazolines
Synthesis

ASJC Scopus subject areas

Pharmacology
Drug Discovery
Organic Chemistry

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10.1016/j.ejmech.2013.05.044

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title = "Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones",

abstract = "A series of novel 5-pyrazoline substituted 4-thiazolidinones have been synthesized. Target compounds were evaluated for their anticancer activity in vitro within DTP NCI protocol. Among the tested compounds, the derivatives 4d and 4f were found to be the most active, which demonstrated certain sensitivity profile toward the leukemia subpanel cell lines with GI50 value ranges of 2.12-4.58 μM (4d) and 1.64-3.20 μM (4f). The screening of antitrypanosomal and antiviral activities of 5-(3-naphthalen-2-yl-5-aryl-4,5-dihydropyrazol-1-yl)-thiazolidine-2,4-diones was carried out with the promising influence of the mentioned compounds on Trypanosoma brucei, but minimal effect on SARS coronavirus and influenza types A and B viruses.",

keywords = "4-Thiazolidinones, Anticancer activity, Antitrypanosomal activity, Antiviral activity, Pyrazolines, Synthesis",

author = "Dmytro Havrylyuk and Borys Zimenkovsky and Olexandr Vasylenko and Day, {Craig W.} and Smee, {Donald F.} and Philippe Grellier and Roman Lesyk",

note = "Funding Information: We are grateful to Dr. V.L. Narayanan from Drug Synthesis and Chemistry Branch, National Cancer Institute, Bethesda, MD, USA, for in vitro evaluation of anticancer activity. Evaluations of compounds for antiviral activity were supported by funds from contract N01-AI-15435 from the Virology Branch, Division of Microbiology and Infectious Diseases, National Institute of Allergy and Infectious Diseases, National Institutes of Health , Bethesda, MD, USA. Publisher Copyright: {\textcopyright} 2013 Elsevier Masson SAS.",

year = "2013",

month = aug,

doi = "10.1016/j.ejmech.2013.05.044",

language = "English",

volume = "66",

pages = "228--237",

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AU - Havrylyuk, Dmytro

AU - Zimenkovsky, Borys

AU - Vasylenko, Olexandr

AU - Day, Craig W.

AU - Smee, Donald F.

AU - Grellier, Philippe

AU - Lesyk, Roman

N1 - Funding Information: We are grateful to Dr. V.L. Narayanan from Drug Synthesis and Chemistry Branch, National Cancer Institute, Bethesda, MD, USA, for in vitro evaluation of anticancer activity. Evaluations of compounds for antiviral activity were supported by funds from contract N01-AI-15435 from the Virology Branch, Division of Microbiology and Infectious Diseases, National Institute of Allergy and Infectious Diseases, National Institutes of Health , Bethesda, MD, USA. Publisher Copyright: © 2013 Elsevier Masson SAS.

PY - 2013/8

Y1 - 2013/8

N2 - A series of novel 5-pyrazoline substituted 4-thiazolidinones have been synthesized. Target compounds were evaluated for their anticancer activity in vitro within DTP NCI protocol. Among the tested compounds, the derivatives 4d and 4f were found to be the most active, which demonstrated certain sensitivity profile toward the leukemia subpanel cell lines with GI50 value ranges of 2.12-4.58 μM (4d) and 1.64-3.20 μM (4f). The screening of antitrypanosomal and antiviral activities of 5-(3-naphthalen-2-yl-5-aryl-4,5-dihydropyrazol-1-yl)-thiazolidine-2,4-diones was carried out with the promising influence of the mentioned compounds on Trypanosoma brucei, but minimal effect on SARS coronavirus and influenza types A and B viruses.

AB - A series of novel 5-pyrazoline substituted 4-thiazolidinones have been synthesized. Target compounds were evaluated for their anticancer activity in vitro within DTP NCI protocol. Among the tested compounds, the derivatives 4d and 4f were found to be the most active, which demonstrated certain sensitivity profile toward the leukemia subpanel cell lines with GI50 value ranges of 2.12-4.58 μM (4d) and 1.64-3.20 μM (4f). The screening of antitrypanosomal and antiviral activities of 5-(3-naphthalen-2-yl-5-aryl-4,5-dihydropyrazol-1-yl)-thiazolidine-2,4-diones was carried out with the promising influence of the mentioned compounds on Trypanosoma brucei, but minimal effect on SARS coronavirus and influenza types A and B viruses.

KW - 4-Thiazolidinones

KW - Anticancer activity

KW - Antitrypanosomal activity

KW - Antiviral activity

KW - Pyrazolines

KW - Synthesis

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Synthesis and biological activity evaluation of 5-pyrazoline substituted 4-thiazolidinones

Abstract

Bibliographical note

Keywords

ASJC Scopus subject areas

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