16670-63-6Relevant articles and documents
Investigation of hydro-lipophilic properties of n-alkoxyphenylhydroxynaphthalenecarboxamides ?
Kapustikova, Iva,Bak, Andrzej,Gonec, Tomas,Kos, Jiri,Kozik, Violetta,Jampilek, Josef
, (2018/07/10)
The evaluation of the lipophilic characteristics of biologically active agents is indispensable for the rational design of ADMET-tailored structure–activity models. N-Alkoxy-3-hydroxynaphthalene-2-carboxanilides, N-alkoxy-1-hydroxynaphthalene-2-carboxanilides, and N-alkoxy-2-hydroxynaphthalene-1-carboxanilides were recently reported as a series of compounds with antimycobacterial, antibacterial, and herbicidal activity. As it was found that the lipophilicity of these biologically active agents determines their activity, the hydro-lipophilic properties of all three series were investigated in this study. All 57 anilides were analyzed using the reversed-phase high-performance liquid chromatography method for the measurement of lipophilicity. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, a range of software lipophilicity predictors for the estimation of clogP values of a set of N-alkoxyphenylhydroxynaphthalenecarboxamides was employed and subsequently cross-compared with experimental parameters. Thus, the empirical values of lipophilicity (logk) and the distributive parameters (π) were compared with the corresponding in silico characteristics that were calculated using alternative methods for deducing the lipophilic features. To scrutinize (dis)similarities between the derivatives, a PCA procedure was applied to visualize the major differences in the performance of molecules with respect to their lipophilic profile, molecular weight, and violations of Lipinski’s Rule of Five.
N-alkoxyphenylhydroxynaphthalenecarboxamides and their antimycobacterial activity
Gonec, Tomas,Pospisilova, Sarka,Kauerova, Tereza,Kos, Jiri,Dohanosova, Jana,Oravec, Michal,Kollar, Peter,Coffey, Aidan,Liptaj, Tibor,Cizek, Alois,Jampilek, Josef
, (2016/08/30)
A series of nineteen N-(alkoxyphenyl)-2-hydroxynaphthalene-1-carboxamides and a series of their nineteen positional isomers N-(alkoxyphenyl)-1-hydroxynaphthalene-2-carboxamides were prepared and characterized. Primary in vitro screening of all the synthes
Synthesis, antimicrobial, and QSAR studies of substituted benzamides
Kumar, Anil,Narasimhan, Balasubramanian,Kumar, Devinder
, p. 4113 - 4124 (2008/03/11)
A series of new substituted benzamides were synthesized and tested in vitro for their antibacterial activity against Gram-positive and Gram-negative bacteria and as well for antifungal activity. The compounds 8i and 9 showed better activity among the different benzamides synthesized. The structural characteristics governing antibacterial activities of substituted benzamides were studied using QSAR methodology. The results showed that the antimicrobial activity could be modeled using the topological descriptors, molecular connectivity indices (2χv and 2χ) and Kiers shape index (κα1). The low residual activity and high cross-validated r2 values (rcv2) observed indicated the predictive ability of the developed QSAR models.