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.
TY - JOUR
AU - Juranić, Ivan
AU - Drakulić, Branko
AU - Petrović, Slobodan
AU - Mijin, Dušan
AU - Stanković, Miroslav
PY - 2006
UR - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/1001
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 - Pergamon-Elsevier Science Ltd, Oxford
T2 - Chemosphere
T1 - A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats
EP - 649
IS - 4
SP - 641
VL - 62
DO - 10.1016/j.chemosphere.2005.05.005
ER -
@article{
author = "Juranić, Ivan and Drakulić, Branko and Petrović, Slobodan 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 = "Pergamon-Elsevier Science Ltd, Oxford",
journal = "Chemosphere",
title = "A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats",
pages = "649-641",
number = "4",
volume = "62",
doi = "10.1016/j.chemosphere.2005.05.005"
}
Juranić, I., Drakulić, B., Petrović, S., Mijin, D.,& Stanković, M.. (2006). A QSAR study of acute toxicity of N-substituted fluoroacetamides to rats. in Chemosphere
Pergamon-Elsevier Science Ltd, Oxford., 62(4), 641-649.
https://doi.org/10.1016/j.chemosphere.2005.05.005
Juranić I, Drakulić B, Petrović S, 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, 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 . .
