The electrotopological state: structure information at the atomic level for molecular graphs

Hall, Lowell H.; Mohney, Brian K.; Kier, Lemont B.

doi:10.1021/ci00001a012

Cited by 291 publications

(187 citation statements)

References 3 publications

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“…Doxorubicin was used as the positive control drug. The IC 50 values obtained for these compounds are listed in Table 3. None of the tested compounds displayed any significant cytotoxicity, thereby providing a high therapeutic index.…”

Section: )mentioning

confidence: 99%

“…Selectivity index (SI) is used to estimate the therapeutic effect of a drug and to identify drug candidates for further studies. SI of each compound was determined as the ratio of IC 50 to MIC (Table 3). It was reported that, new drugs candidates must have SI equal or higher than 1.…”

Section: )mentioning

confidence: 99%

“…Estate keys calculate the sums of the electrotopological state (E-state) values and/or the counts of each atom type. 50,51) ES_Count_aasC calculates the E-state count for carbon with two aromatic bonds and one single bond. Moreover, Jurs descriptors are those ones that combine shape and electronic information to characterize molecules.…”

Section: D Qsar Study Development Of Qsar Modelsmentioning

confidence: 99%

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Synthesis, in Vitro and in Silico Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents

Abdel‐Aziz

Eldehna

Farès

et al. 2015

Biological & Pharmaceutical Bulletin

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In this study, we synthesized two series of novel 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e in addition to a third series of thiophene-2-carbohydrazides 23a-g to develop potent antimicrobial and/or antitubercular agents. The newly synthesized compounds were evaluated in vitro for their antimicrobial and antimycobacterial activities. Most of the 5-nitrofuran-2-carbohydrazides 21a-h and 22a-e displayed variable activity against Aspergillus fumigates, Staphylococcus aureus, Streptococcus pneumonia, Bacillis subtilis, Salmonella typhimurium, Klebsiella pneumonia, Escherichia coli and Mycobacterium tuberculosis. The sulfonamide derivative 21f exhibited superior potency and broad-spectrum antimicrobial activity with minimum inhibitory concentration (MIC) 0.06-0.98 µg/mL and antimycobacterial activity with MIC 3.9 µg/mL. The 5-nitrofuran-2-carbohydrazides 21a, b, g, h and 22a-c exhibited significant antibacterial activity with MIC values in the range of 0.12-7.81 µg/mL. The significances of the 5-nitrofuran moiety and sulfonamide function were explored via the structure-activity relationship (SAR) study. In addition, docking studies revealed that the p-amino benzoic acid (PABA) and binding pockets of the dihydropteroate synthase (DHPS) were successfully occupied by compound 21f. Furthermore, two quantitative structure-activity relationship (QSAR) models were built to explore the structural requirements which controlled the activity.

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Section: )mentioning

confidence: 99%

Section: )mentioning

confidence: 99%

Section: D Qsar Study Development Of Qsar Modelsmentioning

confidence: 99%

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Synthesis, in Vitro and in Silico Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents

Abdel‐Aziz

Eldehna

Farès

et al. 2015

Biological & Pharmaceutical Bulletin

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“…Therefore, it can be confirmed that the difference between the model prediction capacity and the random prediction in our model is of statistical significance. The geometrical descriptors that incorporate atom type pairs and distances were reported to be able to enhance prediction of the behavior of protein-ligand scoring functions (Deng et al, 2004), and the structural basis for the proliferation inhibition of MVLN cells was identified as the ratio of valence electrons to sigma electrons and related electronegativity, as well as stereochemical properties of QXXs that incorporate atom type pairs and distances (Hall et al, 1991;Deng et al, 2004).…”

Section: Transactivation In Mvln Cellsmentioning

confidence: 99%

An exploration of the estrogen receptor transcription activity of capsaicin analogues via an integrated approach based on in silico prediction and in vitro assays

Lin

et al. 2014

Toxicology Letters

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“…17 In general, high accuracy is obtained for QSPRs developed specifically for homologous series and data sets containing similar compound families. 18 QSPRs developed for heterogeneous data sets using topological descriptors [30][31][32] have performed with reported errors comparable to those of group contribution methods. 19,20 For example, the so-called VLOGP model 20 that utilizes a set of over 300 electrotopological-state 32 and kappa shape indices as chemical descriptors was developed using a training set of 6675 compounds (-3.56e logK ow e 7.73) and performed with an average error of 0.201 logK ow units.…”

Section: Introductionmentioning

confidence: 99%

Fuzzy ARTMAP and Back-Propagation Neural Networks Based Quantitative Structure−Property Relationships (QSPRs) for Octanol−Water Partition Coefficient of Organic Compounds

Yaffe

Cohen

Espinosa

et al. 2002

J. Chem. Inf. Comput. Sci.

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Quantitative structure-property relationships (QSPRs) for estimating the logarithm octanol/water partition coefficients, logK ow , at 25°C were developed based on fuzzy ARTMAP and back-propagation neural networks using a heterogeneous set of 442 organic compounds. The set of molecular descriptors were derived from molecular connectivity indices and quantum chemical descriptors calculated from PM3 semiempirical MOtheory. Quantum chemical input descriptors include average polarizability, dipole moments, exchange energy, total electrostatic interaction energy, total two-center energy, and ionization potential. The fuzzy ARTMAP/ QSPR performed, for a logK ow range of -1.6 to 7.9, with average absolute errors of 0.03 and 0.14 logK ow for the overall data and test sets, respectively. The optimal 12-11-1 back-propagation/QSPR model, for the same range of logK ow , exhibited larger average absolute errors of 0.23 and 0.27 logK ow for the test and validation data sets, respectively, over the same range of logK ow values. The present results with the fuzzy ARTMAP-based QSPR are encouraging and suggest that high performance logK ow QSPR that encompasses a wider range of chemical groups could be developed, following the present approach, by training with a larger heterogeneous data set.

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The electrotopological state: structure information at the atomic level for molecular graphs

Cited by 291 publications

References 3 publications

Synthesis, <i>in Vitro</i> and <i>in Silico</i> Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents

Synthesis, <i>in Vitro</i> and <i>in Silico</i> Studies of Some Novel 5-Nitrofuran-2-yl Hydrazones as Antimicrobial and Antitubercular Agents

An exploration of the estrogen receptor transcription activity of capsaicin analogues via an integrated approach based on in silico prediction and in vitro assays

Fuzzy ARTMAP and Back-Propagation Neural Networks Based Quantitative Structure−Property Relationships (QSPRs) for Octanol−Water Partition Coefficient of Organic Compounds

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