Synthesis and QSAR Studies on the Antifungal Activity of 2,3,4‐Substituted Thiazolidines

Prabhakar, Yenamandra S.; Jain, P. C.; Khan, Zafar K.; Haq, W.; Katti, S. B.

doi:10.1002/qsar.200390035

Cited by 6 publications

(6 citation statements)

References 17 publications

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“…Combinatorial Protocol in Multiple Linear Regression (CP-MLR) [13] is one approach to generate multiple QSAR models to address the structure-activity relations in terms of different sub-structural regions and attributes in predicting the activity. As a part of our ongoing interest in thiazolidines as potent drug scaffolds [14], CP-MLR and partial least squares (PLS) analysis based QSAR studies of the HIV-1 RT inhibitory activity of the thiazolidinones [11,12] have been carried out with an objective to explore the predictive and diagnostic aspects of different sub-structural regions and attributes in addressing the chosen phenomenon.…”

Section: Introductionmentioning

confidence: 99%

CP‐MLR/PLS Directed Structure‐Activity Modeling of the HIV‐1 RT Inhibitory Activity of 2,3‐Diaryl‐1,3‐thiazolidin‐4‐ones

et al. 2004

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A detailed structure-activity relationship study of the HIV-1 Reverse Transcriptase (RT) inhibitory activity of two series of compounds, 2-(2,6-dihalo phenyl)-3-(substituted pyridin-2-yl)-thiazolidin-4-ones and 2-(2,6-Dihalophenyl)-3-(substituted phenyl)-thiazolidin-4-ones, belonging to 2,3-diaryl-thiazolidin-4-ones in terms of physicochemical and structural descriptors have been carried out using combinatorial protocol interfaced multiple linear regression (CP-MLR) and partial least squares (PLS) analysis. The models developed in the study indicate a preference for hydrophobic compounds for better inhibitory activity. Also, a positive regression coefficient of I 2,3 , an indicator descriptor meant for the joint disposition of substituents of 2,3-diaryl moieties of thiazolidinones to address their ability in taking a butterfly like conformation, is in agreement with all earlier observations that compounds having the ability to take butterfly like conformation will be showing better inhibitory activity. The identified models suggest that the meta-positions of 3-aryl moiety has the ability to accommodate hydrophobic/ steric groups. The replacement of C2'' of 3-phenyl by nitrogen resulted in 3-pyridyl variants of these analogues. Even though from geometry point of view, the phenyls and pyridyls span almost the same structural space and steric features, presence of nitrogen in pyridyls gave them a blend of polarity, electronic features and a different hydrophobicity profile when compared to corresponding phenyl analogue. Furthermore the PLS models, developed from those descriptors took part in CP-MLR models, indicate that most of the descriptors have almost equal influence in accounting for the variation in the activity of these compounds. This suggests that the factors responsible for the variation in the activity have been uniformly distributed across the varying centers of the molecule. The study suggests that thiazolidinones with 3-(pyridin-2-yl) moiety provide scope for further substituent variation to modulate the HIV-1 RT inhibitory activity.

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Section: Introductionmentioning

confidence: 99%

CP‐MLR/PLS Directed Structure‐Activity Modeling of the HIV‐1 RT Inhibitory Activity of 2,3‐Diaryl‐1,3‐thiazolidin‐4‐ones

et al. 2004

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“…Eigenvalue describes the shape of the molecule and polarizability is an indication of ease to induce a dipole moment. QSAR studies carried out on antifungal activity of substituted thiazolidines lead to the conclusions that steric and electronic properties are the essential parameters [8]. QSAR models for the mutagenicity and carcinogenicity of simple aldehydes and unsaturated aldehydes pointed to the role of electrophilicity, bulkiness, and hydrophobicity as the important parameters [20].…”

Section: Resultsmentioning

confidence: 99%

“…Wiktorowicz et al have studied the quantitative structure activity relationships of a series of imidazole derivatives as potential new antifungal drugs [7]. Prabhakar et al have synthesised 2,3,4-substituted thiazolidines and studied their antifungal activity against Candida albicans, Cryptococcus neoformans, Tricophyton mentagrophyte and Aspergillus fumigatus [8]. The present paper discusses experimental and QSAR studies carried out on a set of organic compounds tested for their antifungal activity against Aspergillus niger and Fusarium Rosium.…”

Section: Introductionmentioning

confidence: 99%

Experimental and modelling studies on antifungal compounds

Doble

Kumar

2006

Open Chemistry

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Antifungal activity of organic compounds (aromatic, salicylic derivatives, cinnamyl derivatives etc) on Fusarium Rosium (14 compounds) and Aspergillus niger (17 compounds) was studied and QSAR models were developed relating molecular descriptors with the observed activity. Back propagation Neural Network models and single and multiple regression models were tested for predicting the observed activity. The data fit as well as the predictive capability of the neural network models were satisfactory (R 2 = 0.84, q 2 = 0.73 for Fusarium Rosium and R 2 = 0.75, q 2 = 0.62 for Aspergillus niger ). The descriptors used in the network for the former were X4 (connectivity) and Jhetv (topological); and TIC1 (information) and SPI (topological) for the latter fungus. Antifungal activities of these organic compounds were generally lower against the latter than with the former fungus.

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“…Wiktorowicz et al [17] have studied the quantitative structure-activity relationships of a series of imidazole derivatives as potential new antifungal drugs. Prabhakar et al [18] have synthesised 2,3,4-substituted thiazolidines and studied their antifungal activity against Candida albicans, Cryptococcus neoformans, Tricophyton mentagrophyte and Aspergillus fumigatus and developed a QSAR based on the structural descriptors.…”

Section: Fig 1 Structure Of Podophylotoxinmentioning

confidence: 99%

Synthesis, anti-fungal activity evaluation and QSAR studies on podophyllotoxin derivatives

et al. 2007

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Abstract:The anti-fungal and cytotoxic activites of podophyllotoxin and seven C-4 substituted podophyllotoxin ester derivatives, viz: trans-cinnamyl, cis-cinnamyl, o-methoxy cinnamyl, dimethyl acrylyl, p-methoxy phenyl acetyl, 3,4-dimethoxy phenyl acetyl and 2,5-dimethoxy phenyl acetyl esters were evaluated on four fungi, viz: Macrophomina phaseolina, Fusarium oxysporum, Myrrothecium verrucarria and Asperigillus candidus, The podophyllotoxin derivatives were synthesised and their structures were elucidated. Quantitative structure activity relationships were developed between the activity of these compounds against the four fungi and molecular descriptors. The linear regression models developed had one to two descriptors. For all the cases the r 2 was in the range of 0.73 to 0.96, indicating good data fit and q 2 was in the range of 0.60 to 0.68, indicating that the predictive capabilities of the models were acceptable. Solvent accessible surface area (namely the partial positive solvent-accessible surface area), A log P , highest occupied molecular orbital and conformational energy were identified as important descriptors.

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Synthesis and QSAR Studies on the Antifungal Activity of 2,3,4‐Substituted Thiazolidines

Cited by 6 publications

References 17 publications

CP‐MLR/PLS Directed Structure‐Activity Modeling of the HIV‐1 RT Inhibitory Activity of 2,3‐Diaryl‐1,3‐thiazolidin‐4‐ones

CP‐MLR/PLS Directed Structure‐Activity Modeling of the HIV‐1 RT Inhibitory Activity of 2,3‐Diaryl‐1,3‐thiazolidin‐4‐ones

Experimental and modelling studies on antifungal compounds

Synthesis, anti-fungal activity evaluation and QSAR studies on podophyllotoxin derivatives

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