Hydroxylation of Aniline by Alcohols

Property Chemical class Variables Method Citation Ref. No. 

Therapeutic type Therapeutics Wt-paths Clustering RandiC 40 

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Sabljic, A. and Protic-Sabljic, M. (1983). Quantitative Structure-Activity Study on the Mechanism of Inhibition of Microsomal p-Hydroxylation of Aniline by Alcohols. Mol.Pharm., 23,... 

Cohen, G.M. and G.J. Mannering (1972). Involvement of a hydrophobic site in the inhibition of the microsomal para-hydroxylation of aniline by alcohols. Mol. Pharmacol. 8, 383-397. 

Basak SC, Gute BD (1997) Use of graph theoretic parameters in predicting inhibition of microsomal hydroxylation of anilines by alcohols a molecular similarity approach. In Johnson BL, Xintaras C, Andrews JS (eds) Proceedings of the international congress on hazardous waste impact on human and ecological health. Princeton Scientific, Princeton, NJ, p 492... 

Amic, D., Lucic, B., Nikolic, S., and Trinajstic, N. (2001) Predicting inhibition of microsomal p-hydroxylation of aniline by aliphatic alcohols a QSAR approach based on the weighted path numbers. Croat. Chem. Acta 74, 237-250. 

Sabljic has investigated a series of aliphatic alcohols which inhibit the p-hydroxylation of anilines by cytochrome P-450.For the 20 alcohols studied, it was found that an inverse relation exists between the activity and the Addition of the Xpc index yields a satisfactory QSAR equation ... 

Schiff bases from substituted and unsubstituted benzaldehyde and aliphatic or aromatic amines are more stable [6-8]. Benzaldehyde substituents such as nitro, dialkylamino, hydroxyl, methoxyl, or halo have been used [7a-c]. Benzalaniline, m.p. 51°-52°C, is prepared in 87% yield by adding 1.0 mole of aniline to 1.0 mole of benzaldehyde at room temperature in the absence of a solvent. The crude product is added to alcohol [5] in order to induce crystallization [6]. 

B. Testa, Chem.—Biol. Interact., 34, 287 (1981). Structural and Electronic Factors Influencing the Inhibition of Aniline Hydroxylation by Alcohols and Their Binding to Cytochrome P-450. 

Trinitroaniline, orange-red crystals from alcohol, m.p. 186 1 has but little interest as an explosive for the reason that other more powerful and more valuable explosives may be prepared from the same raw materials. It may be prepared by nitrating aniline in glacial acetic acid solution or by the use of mixed nitric-sulfuric acid in which no large excess of sulfuric acid is present. The presence of nitrous acid must be avoided, as this attacks the amino group, replaces it by hydroxyl, and results in the formation of picric acid. The nitration of aniline in the presence of a large amount of concentrated sulfuric acid yields m-nitroaniline and later the nitro compounds which are derived from it. 

Testa, B. (1981), Structural and electronic factors influencing the inhibition of aniline hydroxylation by alcohols and their binding to cytochrome P-450. Chem. Biol. Interact. 34, 287-300. 

Condensation of normeperidine (81) with 3-chloropropan-l-ol affords the compound possessing the alcohol side chain (88). The hydroxyl is then converted to chlorine by means of thionyl chloride (89) displacement of the halogen by aniline yields pimino-dine (90). ° Condensation of the secondary amine, 81, with styrene oxide affords the alcohol, 91 removal of the benzyllic hydroxyl group by hydrogenolysis leads to pheneridlne (92). ... 

For quite sparingly soluble substances, formic acid, pyridine, bromobenzene, nitrobenzene, and occasionally also phenol, ethyl benzoate, aniline, and dioxan are used. A distinct relation exists between the constitution of solute and solvent, and is expressed by the old rule similia similibus solvuntur. Thus, as is well known, substances containing hydroxyl (e.g. sugars, carboxylic acids) are soluble in water, whereas hydrocarbons are more soluble in benzene and petrol ether than, for example, in alcohols. 

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