Carcinogenicity of 5 nitrofurans, 5 nitroimidazoles, 4 nitrobenzenes, and related compounds

Samuel Monroe Cohen, F. Erturk, A. M. von Esch, A. J. Crovetti, G. T. Bryan

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Abstract

1 [(5 Nitrofurfurylidene)amino]hydantoin gave negative results in chronic carcinogenicity tests in rats. Carcinogenic response was moderate for 4 methyl 1 [(5 nitrofurfurylidene)amino] 2 imidazolidinone and 1 (2 hydroxyethyl) 3 [(5 nitrofurfurylidene)amino] 2 imidazolidinone, and strong for l 5 morpholinomethyl 3 [(5 nitrofurfurylidene)amino] 2 oxazolidinone hydrochloride and 1 [(5 nitrofurfurylidene)amino] 2 imidazolidinone. Several other nitrofurans, nitrobenzenes, aminobenzenes, nitroimidazoles, and related compounds were also tested for carcinogenicity with varying results. 5 Nitro 2 furamidoxime, 2 hydrazino 4 phenylthiazole, D (-) threo 1 (p nitrophenyl) 2 dichloracetamido 1,3 propanediol, 1 (2 hydroxyethyl) 2 methyl 5 nitroimidazole, and 2 amino 5 phenyl 2 oxazolin 4 one with Mg(OH)2 gave negative results; hexamethylmelamine and 1,2 dimethyl 5 nitroimidazole were weakly tumorigenic; 4,6 diamino 2 (5 nitro 2 furyl) s triazine and its bisacetamide, formic acid 2 [4(5 nitro 2 furyl) 2 thiazolyl] hydrazide, 2 (2,2 dimethylhydrazino) 4 (5 nitro 2 furyl)thiazole, 2 hydrazino 4(p nitrophenyl)thiazole, and 2 hydrazino 4 (p aminophenyl)thiazole were strongly carcinogenic. The significance of the structural variations is discussed with respect to nitrofuran carcinogenesis and the possible carcinogenicity of other nitroaromatic compounds.

Original languageEnglish (US)
Pages (from-to)403-417
Number of pages15
JournalJournal of the National Cancer Institute
Volume51
Issue number2
StatePublished - Dec 1 1973

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Nitrobenzenes
Nitrofurans
Thiazoles
Altretamine
Carcinogenicity Tests
Hydantoins
Nitroimidazoles
Triazines
Carcinogenesis
4-nitroimidazole
ethylene urea

ASJC Scopus subject areas

  • Cancer Research
  • Oncology

Cite this

Carcinogenicity of 5 nitrofurans, 5 nitroimidazoles, 4 nitrobenzenes, and related compounds. / Cohen, Samuel Monroe; Erturk, F.; von Esch, A. M.; Crovetti, A. J.; Bryan, G. T.

In: Journal of the National Cancer Institute, Vol. 51, No. 2, 01.12.1973, p. 403-417.

Research output: Contribution to journalArticle

Cohen, Samuel Monroe ; Erturk, F. ; von Esch, A. M. ; Crovetti, A. J. ; Bryan, G. T. / Carcinogenicity of 5 nitrofurans, 5 nitroimidazoles, 4 nitrobenzenes, and related compounds. In: Journal of the National Cancer Institute. 1973 ; Vol. 51, No. 2. pp. 403-417.
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abstract = "1 [(5 Nitrofurfurylidene)amino]hydantoin gave negative results in chronic carcinogenicity tests in rats. Carcinogenic response was moderate for 4 methyl 1 [(5 nitrofurfurylidene)amino] 2 imidazolidinone and 1 (2 hydroxyethyl) 3 [(5 nitrofurfurylidene)amino] 2 imidazolidinone, and strong for l 5 morpholinomethyl 3 [(5 nitrofurfurylidene)amino] 2 oxazolidinone hydrochloride and 1 [(5 nitrofurfurylidene)amino] 2 imidazolidinone. Several other nitrofurans, nitrobenzenes, aminobenzenes, nitroimidazoles, and related compounds were also tested for carcinogenicity with varying results. 5 Nitro 2 furamidoxime, 2 hydrazino 4 phenylthiazole, D (-) threo 1 (p nitrophenyl) 2 dichloracetamido 1,3 propanediol, 1 (2 hydroxyethyl) 2 methyl 5 nitroimidazole, and 2 amino 5 phenyl 2 oxazolin 4 one with Mg(OH)2 gave negative results; hexamethylmelamine and 1,2 dimethyl 5 nitroimidazole were weakly tumorigenic; 4,6 diamino 2 (5 nitro 2 furyl) s triazine and its bisacetamide, formic acid 2 [4(5 nitro 2 furyl) 2 thiazolyl] hydrazide, 2 (2,2 dimethylhydrazino) 4 (5 nitro 2 furyl)thiazole, 2 hydrazino 4(p nitrophenyl)thiazole, and 2 hydrazino 4 (p aminophenyl)thiazole were strongly carcinogenic. The significance of the structural variations is discussed with respect to nitrofuran carcinogenesis and the possible carcinogenicity of other nitroaromatic compounds.",
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AU - Cohen, Samuel Monroe

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AU - Crovetti, A. J.

AU - Bryan, G. T.

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N2 - 1 [(5 Nitrofurfurylidene)amino]hydantoin gave negative results in chronic carcinogenicity tests in rats. Carcinogenic response was moderate for 4 methyl 1 [(5 nitrofurfurylidene)amino] 2 imidazolidinone and 1 (2 hydroxyethyl) 3 [(5 nitrofurfurylidene)amino] 2 imidazolidinone, and strong for l 5 morpholinomethyl 3 [(5 nitrofurfurylidene)amino] 2 oxazolidinone hydrochloride and 1 [(5 nitrofurfurylidene)amino] 2 imidazolidinone. Several other nitrofurans, nitrobenzenes, aminobenzenes, nitroimidazoles, and related compounds were also tested for carcinogenicity with varying results. 5 Nitro 2 furamidoxime, 2 hydrazino 4 phenylthiazole, D (-) threo 1 (p nitrophenyl) 2 dichloracetamido 1,3 propanediol, 1 (2 hydroxyethyl) 2 methyl 5 nitroimidazole, and 2 amino 5 phenyl 2 oxazolin 4 one with Mg(OH)2 gave negative results; hexamethylmelamine and 1,2 dimethyl 5 nitroimidazole were weakly tumorigenic; 4,6 diamino 2 (5 nitro 2 furyl) s triazine and its bisacetamide, formic acid 2 [4(5 nitro 2 furyl) 2 thiazolyl] hydrazide, 2 (2,2 dimethylhydrazino) 4 (5 nitro 2 furyl)thiazole, 2 hydrazino 4(p nitrophenyl)thiazole, and 2 hydrazino 4 (p aminophenyl)thiazole were strongly carcinogenic. The significance of the structural variations is discussed with respect to nitrofuran carcinogenesis and the possible carcinogenicity of other nitroaromatic compounds.

AB - 1 [(5 Nitrofurfurylidene)amino]hydantoin gave negative results in chronic carcinogenicity tests in rats. Carcinogenic response was moderate for 4 methyl 1 [(5 nitrofurfurylidene)amino] 2 imidazolidinone and 1 (2 hydroxyethyl) 3 [(5 nitrofurfurylidene)amino] 2 imidazolidinone, and strong for l 5 morpholinomethyl 3 [(5 nitrofurfurylidene)amino] 2 oxazolidinone hydrochloride and 1 [(5 nitrofurfurylidene)amino] 2 imidazolidinone. Several other nitrofurans, nitrobenzenes, aminobenzenes, nitroimidazoles, and related compounds were also tested for carcinogenicity with varying results. 5 Nitro 2 furamidoxime, 2 hydrazino 4 phenylthiazole, D (-) threo 1 (p nitrophenyl) 2 dichloracetamido 1,3 propanediol, 1 (2 hydroxyethyl) 2 methyl 5 nitroimidazole, and 2 amino 5 phenyl 2 oxazolin 4 one with Mg(OH)2 gave negative results; hexamethylmelamine and 1,2 dimethyl 5 nitroimidazole were weakly tumorigenic; 4,6 diamino 2 (5 nitro 2 furyl) s triazine and its bisacetamide, formic acid 2 [4(5 nitro 2 furyl) 2 thiazolyl] hydrazide, 2 (2,2 dimethylhydrazino) 4 (5 nitro 2 furyl)thiazole, 2 hydrazino 4(p nitrophenyl)thiazole, and 2 hydrazino 4 (p aminophenyl)thiazole were strongly carcinogenic. The significance of the structural variations is discussed with respect to nitrofuran carcinogenesis and the possible carcinogenicity of other nitroaromatic compounds.

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