Synthesis and in vitro cytotoxicity of 5-substituted 2-cyanoimino-4-imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives

A series of 5-substituted 2-cyanoimino-4-imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives were synthesized and their anticancer cytotoxicity were evaluated in in vitro assay. It was found that the bulky aryl functionality in the 5-position of the 2-cyanoimino-4-imidazolidinone compounds was...

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Published inBioorganic & medicinal chemistry letters Vol. 14; no. 5; pp. 1169 - 1172
Main Authors CHERN, Jyh-Haur, SHIA, Kak-Shan, CHANG, Chung-Ming, LEE, Chung-Chi, LEE, Yen-Chun, TAI, Chia-Liang, LIN, Ying-Ting, CHANG, Chih-Shiang, TSENG, Huan-Yi
Format Journal Article
LanguageEnglish
Published Oxford Elsevier 08.03.2004
Subjects
Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - toxicity
Biological and medical sciences
Cell Line, Tumor
Fibroblasts - drug effects
General aspects
Humans
Imidazoles - chemical synthesis
Imidazoles - toxicity
Medical sciences
Pharmacology. Drug treatments
Pyrimidinones - chemical synthesis
Pyrimidinones - toxicity
Antineoplastic agent
Five membered ring
Nitrogen heterocycle
Toxicity
Cytotoxicity
In vitro
Pyridine derivatives
Cell line
Structure activity relation
Six membered ring
Chemical synthesis
Fibroblast
Tumor cell
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Abstract A series of 5-substituted 2-cyanoimino-4-imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives were synthesized and their anticancer cytotoxicity were evaluated in in vitro assay. It was found that the bulky aryl functionality in the 5-position of the 2-cyanoimino-4-imidazolidinone compounds was essential for the cytotoxicity of these heterocyclic compounds. Some of the derivatives exhibited modest cytotoxicity against a variety of cancer cell lines. One of the derivatives, [1-[6-(4-chlorophenoxy)hexyl]-5-oxo-4-phenyl-3-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]aminomethanenitrile (Compound 11), exhibited the most potent cytotoxic activity with IC(50) in the nanomolar range. The cytotoxicity of these derivatives was selection with no apparent toxic effect toward normal fibroblasts.
AbstractList A series of 5-substituted 2-cyanoimino-4-imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives were synthesized and their anticancer cytotoxicity were evaluated in in vitro assay. It was found that the bulky aryl functionality in the 5-position of the 2-cyanoimino-4-imidazolidinone compounds was essential for the cytotoxicity of these heterocyclic compounds. Some of the derivatives exhibited modest cytotoxicity against a variety of cancer cell lines. One of the derivatives, [1-[6-(4-chlorophenoxy)hexyl]-5-oxo-4-phenyl-3-(4-pyridyl)tetrahydro-1H-2-imidazolyliden]aminomethanenitrile (Compound 11), exhibited the most potent cytotoxic activity with IC(50) in the nanomolar range. The cytotoxicity of these derivatives was selection with no apparent toxic effect toward normal fibroblasts.
Author CHANG, Chih-Shiang
CHERN, Jyh-Haur
LIN, Ying-Ting
LEE, Chung-Chi
TSENG, Huan-Yi
CHANG, Chung-Ming
SHIA, Kak-Shan
LEE, Yen-Chun
TAI, Chia-Liang
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Issue 5
Keywords Antineoplastic agent
Five membered ring
Nitrogen heterocycle
Toxicity
Cytotoxicity
In vitro
Pyridine derivatives
Cell line
Structure activity relation
Six membered ring
Chemical synthesis
Fibroblast
Tumor cell
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Snippet A series of 5-substituted 2-cyanoimino-4-imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives were synthesized and their anticancer cytotoxicity were...
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SubjectTerms Antineoplastic agents
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - toxicity
Biological and medical sciences
Cell Line, Tumor
Fibroblasts - drug effects
General aspects
Humans
Imidazoles - chemical synthesis
Imidazoles - toxicity
Medical sciences
Pharmacology. Drug treatments
Pyrimidinones - chemical synthesis
Pyrimidinones - toxicity
Title Synthesis and in vitro cytotoxicity of 5-substituted 2-cyanoimino-4-imidazodinone and 2-cyanoimino-4-pyrimidinone derivatives
URI https://www.ncbi.nlm.nih.gov/pubmed/14980658
Volume 14
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