A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats
Abstract
Acute toxicity in vivo toward rats, of nineteen N-alkyl and N-cycloalkyl fluorocetamides [F-CH2-C(O)-NH-R] was correlated with their structure-dependent properties. Used descriptors are: molecular weights (M-w) and heat of formation (Delta H-f) of compounds; molar refractivity (CMR), lipophilicity (Clog P), Broto lipol values, virtual log P, molecular lipophilic potential (MLP), Van der Waals surfaces (VdW SAS) and hydropathicity surface (ILM) of whole molecules; Taft steric parameters (E-s); E-s values with Hancock corrections (E-s(CH)) and Verloop sterimol (B-5) and (L) parameters of alkyl and cycloalkyl residues; superdelocalizabilities and electron densities on the [NH-C(O)-CH2-F] fragment. Strong quantitative structure-activity relationships were assessed. Obtained correlation suggested that lipophilicity, shape and bulkiness of the alkyl and cycloalkyl substituents, particular nearest vicinity of the amide nitrogen, as well charges on the amide moiety are the main factors that in...fluence on the acute toxicity of studied compounds toward rats. Mechanism of toxic action was proposed.
Keywords:
acute toxicity / rats / N-alkyl fluoracetamides / QSARSource:
Chemosphere, 2006, 62, 4, 641-649Publisher:
- Oxford : Pergamon-Elsevier Science Ltd
Funding / projects:
- Ministry of Science and Environmental Protection of Serbia, Research grant 1694
- Ministry of Science and Environmen-tal Protection of Serbia, Research grant 1253
DOI: 10.1016/j.chemosphere.2005.05.005
ISSN: 0045-6535
PubMed: 16002123
WoS: 000234955800016
Scopus: 2-s2.0-28444489246
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Institution/Community
IHTMTY - JOUR AU - Juranić, Ivan AU - Drakulić, Branko AU - Petrović, Slobodan D. AU - Mijin, Dušan AU - Stanković, Miroslav PY - 2006 UR - https://cer.ihtm.bg.ac.rs/handle/123456789/242 AB - Acute toxicity in vivo toward rats, of nineteen N-alkyl and N-cycloalkyl fluorocetamides [F-CH2-C(O)-NH-R] was correlated with their structure-dependent properties. Used descriptors are: molecular weights (M-w) and heat of formation (Delta H-f) of compounds; molar refractivity (CMR), lipophilicity (Clog P), Broto lipol values, virtual log P, molecular lipophilic potential (MLP), Van der Waals surfaces (VdW SAS) and hydropathicity surface (ILM) of whole molecules; Taft steric parameters (E-s); E-s values with Hancock corrections (E-s(CH)) and Verloop sterimol (B-5) and (L) parameters of alkyl and cycloalkyl residues; superdelocalizabilities and electron densities on the [NH-C(O)-CH2-F] fragment. Strong quantitative structure-activity relationships were assessed. Obtained correlation suggested that lipophilicity, shape and bulkiness of the alkyl and cycloalkyl substituents, particular nearest vicinity of the amide nitrogen, as well charges on the amide moiety are the main factors that influence on the acute toxicity of studied compounds toward rats. Mechanism of toxic action was proposed. PB - Oxford : Pergamon-Elsevier Science Ltd T2 - Chemosphere T1 - A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats VL - 62 IS - 4 SP - 641 EP - 649 DO - 10.1016/j.chemosphere.2005.05.005 ER -
@article{ author = "Juranić, Ivan and Drakulić, Branko and Petrović, Slobodan D. and Mijin, Dušan and Stanković, Miroslav", year = "2006", abstract = "Acute toxicity in vivo toward rats, of nineteen N-alkyl and N-cycloalkyl fluorocetamides [F-CH2-C(O)-NH-R] was correlated with their structure-dependent properties. Used descriptors are: molecular weights (M-w) and heat of formation (Delta H-f) of compounds; molar refractivity (CMR), lipophilicity (Clog P), Broto lipol values, virtual log P, molecular lipophilic potential (MLP), Van der Waals surfaces (VdW SAS) and hydropathicity surface (ILM) of whole molecules; Taft steric parameters (E-s); E-s values with Hancock corrections (E-s(CH)) and Verloop sterimol (B-5) and (L) parameters of alkyl and cycloalkyl residues; superdelocalizabilities and electron densities on the [NH-C(O)-CH2-F] fragment. Strong quantitative structure-activity relationships were assessed. Obtained correlation suggested that lipophilicity, shape and bulkiness of the alkyl and cycloalkyl substituents, particular nearest vicinity of the amide nitrogen, as well charges on the amide moiety are the main factors that influence on the acute toxicity of studied compounds toward rats. Mechanism of toxic action was proposed.", publisher = "Oxford : Pergamon-Elsevier Science Ltd", journal = "Chemosphere", title = "A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats", volume = "62", number = "4", pages = "641-649", doi = "10.1016/j.chemosphere.2005.05.005" }
Juranić, I., Drakulić, B., Petrović, S. D., Mijin, D.,& Stanković, M.. (2006). A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats. in Chemosphere Oxford : Pergamon-Elsevier Science Ltd., 62(4), 641-649. https://doi.org/10.1016/j.chemosphere.2005.05.005
Juranić I, Drakulić B, Petrović SD, Mijin D, Stanković M. A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats. in Chemosphere. 2006;62(4):641-649. doi:10.1016/j.chemosphere.2005.05.005 .
Juranić, Ivan, Drakulić, Branko, Petrović, Slobodan D., Mijin, Dušan, Stanković, Miroslav, "A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats" in Chemosphere, 62, no. 4 (2006):641-649, https://doi.org/10.1016/j.chemosphere.2005.05.005 . .