Structure-activity study of bacteriostatic kojic acid analogs.

Kotani, Takashi; Ichimoto, Itsuo; Tatsumi, Chuji; Fujita, Toshio

doi:10.1271/bbb1961.39.1311

Cited by 12 publications

(9 citation statements)

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“…Kojic acid is thought to act against some bacteria because of its chelating ability.1) However, according to a recent analysis, kojic acid and its analogs, with vari ous degrees of antibacterial action, probably act as free neutral molecules at the cell surface of the bacteria when common metallic ions are neither in excess nor depleted. 2) Here, we report supporting evidence for this previous analysis. We studied the re lationships between structure and chelating potency, and bacteriostatic activities under metal-depleted and -excess conditions using a series of analogs (I) where the 2-and 7positions have various substituents.…”

supporting

confidence: 89%

Bacteriostatic activities and metal chelation of kojic acid analogs.

Kotani

Ichimoto

Tatsumi

et al. 1976

Agricultural and Biological Chemistry

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The relationship between structure and activity in bacteriostasis was compared to the relationship between structure and reactivity in metal chelate formation for various kojic acid analogs. The metal chelating property with Cu2+ and Cd2+ was closely related to the acid dissociation constant.Since structure-activity analyses showed that the neutral molecule is the active form, and since the pKA value as the electronic parameter is re lated to the activity only for the neutral molecule but not for the ionized form, it was postu lated that metal chelate formation is not significant for manifestation of the bacteriostatic activity of this series of compounds.This postulation was confirmed in experiments under conditions in which the metal was depleted or excessive. The bacteriostatic activity of kojic acid analogs against such bacteria as S. aureus 209P, E. coli K-12 and Ps. fluorescens was neither retarded nor enhanced.

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supporting

confidence: 89%

Bacteriostatic activities and metal chelation of kojic acid analogs.

Kotani

Ichimoto

Tatsumi

et al. 1976

Agricultural and Biological Chemistry

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“…Kojic acid derivatives possess wide-ranging pharmacological activities such as antifungal [4], anti-neoplastic [5], antiproliferative [6], anti-HIV [7], anticonvulsant [8], anti-inflammatory [9], antioxidative [10], antibacterial [11], and tyrosinase inhibitory activities [12]. Because of these valuable properties, kojic acid derivatives are of great interest for the pharmaceutical chemistry.…”

Section: Introductionmentioning

confidence: 99%

MCM-41-SO3H: an efficient, reusable, heterogeneous catalyst for the one-pot, three-component synthesis of pyrano[3,2-b]pyrans

2015

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“…3-Hydroxypyridine-4-one derivatives and their oxygen-containing analogues, 3-hydroxypyran-4-ones, belong to a class of iron chelators with reported in vitro antibacterial, antifungal and antimalarial activities [4][5][6][7]. They have shown inhibitory effects on the growth of Escherichia coli, Listeria inocua and Staphylococcus aureus [8][9][10]. We have previously reported the antimicrobial activities of novel Mannich bases of 2-alkyl-3-hydroxy-pyridine-4-ones as well as 1-alkyl substituted 2-alkyl-3-hydroxypyridine-4-ones.…”

Section: Introductionmentioning

confidence: 99%

Computer-aided design of novel antibacterial 3-hydroxypyridine-4-ones: application of QSAR methods based on the MOLMAP approach

Sabet

Fassihi

Hemmateenejad

et al. 2012

J Comput Aided Mol Des

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3-Hydroxypyridine-4-one derivatives have shown good inhibitory activity against bacterial strains. In this work we report the application of MOLMAP descriptors based on empirical physicochemical properties with genetic algorithm partial least squares (GA-PLS) and counter propagation artificial neural networks (CP-ANN) methods to propose some novel 3-hydroxypyridine-4-one derivatives with improved antibacterial activity against Staphylococcus aureus. A large collection of 302 novel derivatives of this chemical scaffold was selected for this purpose. The activity classes of these compounds were determined using the two quantitative structure activity relationships models. To evaluate the predictability and accuracy of the obtained models, nineteen compounds belonging to all three activity classes were prepared and the activity of them was determined against S. aureus. Comparing the experimental results and the predicted activity classes revealed the accuracy of the obtained models. Seventeen of the nineteen synthesized molecules were correctly predicted by GA-PLS model according to the antimicrobial evaluation method. Molecules 5f and 5h proved to be moderately active and active experimentally, but were predicted as inactive and moderately active compounds, respectively by this model. The CP-ANN based prediction was correct for sixteen out of the nineteen synthesized molecules. 5a, 5h and 5q were moderately active and active based on the antimicrobial assays, but they were introduced as members of inactive, moderately active and inactive classes of compounds, respectively according to CP-ANN model.

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Structure-activity study of bacteriostatic kojic acid analogs.

Cited by 12 publications

References 1 publication

Bacteriostatic activities and metal chelation of kojic acid analogs.

Bacteriostatic activities and metal chelation of kojic acid analogs.

MCM-41-SO3H: an efficient, reusable, heterogeneous catalyst for the one-pot, three-component synthesis of pyrano[3,2-b]pyrans

Computer-aided design of novel antibacterial 3-hydroxypyridine-4-ones: application of QSAR methods based on the MOLMAP approach

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