Loew G H, Sudhindra B S, Walker J M, Sigman C C, Johnson H L
J Environ Pathol Toxicol. 1979 Mar-Apr;2(4):1069-78.
Electronic parameters for a series of amino-, chloro-, and nitro-substituted anilines relative to their potential for activation to hydroxylamines, aryl-nitrenium ions, and ring epoxides, and to their potential deactivation to phenols were calculated using semi-empirical molecular orbital methods. The relative mutagenic activities of aminoanilines could be explained by parameters reflecting potential for N-hydroxylation and stability of the arylnitrenium ions. Both chloro and nitro groups deactivate the amine group to N-hydroxylation and the ring to epoxidation, and no active products from cytochrome P-450 would be predicted. This result is consistent with lack of mutagenic activity observed for chloro derivatives, but does not account for activity of the nitro derivatives, which is presumed to be due to transformation of the nitro group itself to an active mutagenic species by other enzyme systems.
使用半经验分子轨道方法计算了一系列氨基、氯基和硝基取代苯胺的电子参数，这些参数与它们被激活为羟胺、芳基氮鎓离子和环氧化物的可能性以及它们被失活为酚类的可能性有关。氨基苯胺的相对诱变活性可以通过反映N-羟基化潜力和芳基氮鎓离子稳定性的参数来解释。氯基和硝基都使胺基对N-羟基化失活，并使环对环氧化失活，预计细胞色素P-450不会产生活性产物。这一结果与氯衍生物缺乏诱变活性一致，但不能解释硝基衍生物的活性，推测这是由于硝基本身被其他酶系统转化为活性诱变物质所致。
