Respiratory syncytial virus fusion inhibitors. Part 7: Structure–activity relationships associated with a series of isatin oximes that demonstrate antiviral activity in vivo

Sin, Nancy L.; Venables, Brian L.; Combrink, Keith D.; Gulgeze, H. Belgin; Yu, Kai; Civiello, Rita L.; Thuring, Jan Willem; Wang, X. Alan; Yang, Zheng; Zadjura, Lisa; Marino, Anthony M.; Kadow, Kathleen F.; Cianci, Christopher; Clarke, J. L.; Genovesi, Eugene V.; Medina, Ivette; Lamb, Lucinda; Krystal, Mark; Meanwell, Nicholas A.

doi:10.1016/j.bmcl.2009.06.030

Cited by 42 publications

(27 citation statements)

References 22 publications

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“…These results are to some extent in agreement with the corresponding related experimental conclusions [12,13,18]. For example, Yu et al reported that the topology of the side chain of RSV inhibitors is important, while we also find that the corresponding descriptors (D299 and D347) play a part in RSV inhibition.…”

Section: Resultssupporting

confidence: 93%

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A Classification Study of Respiratory Syncytial Virus (RSV) Inhibitors by Variable Selection with Random Forest

Ming

Wang

et al. 2011

IJMS

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Experimental pEC50s for 216 selective respiratory syncytial virus (RSV) inhibitors are used to develop classification models as a potential screening tool for a large library of target compounds. Variable selection algorithm coupled with random forests (VS-RF) is used to extract the physicochemical features most relevant to the RSV inhibition. Based on the selected small set of descriptors, four other widely used approaches, i.e., support vector machine (SVM), Gaussian process (GP), linear discriminant analysis (LDA) and k nearest neighbors (kNN) routines are also employed and compared with the VS-RF method in terms of several of rigorous evaluation criteria. The obtained results indicate that the VS-RF model is a powerful tool for classification of RSV inhibitors, producing the highest overall accuracy of 94.34% for the external prediction set, which significantly outperforms the other four methods with the average accuracy of 80.66%. The proposed model with excellent prediction capacity from internal to external quality should be important for screening and optimization of potential RSV inhibitors prior to chemical synthesis in drug development.

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Section: Resultssupporting

confidence: 93%

“…Chapman et al [11] also reported the discovery and initial development of RSV604, a novel benzodiazepine with submicromolar anti-RSV activity. In addition, with continuous efforts, Meanwell and colleagues have examined several of benzimidazole derivatives with highly potent RSV inhibition activity [12–18]. …”

Section: Introductionmentioning

confidence: 99%

A Classification Study of Respiratory Syncytial Virus (RSV) Inhibitors by Variable Selection with Random Forest

Ming

Wang

et al. 2011

IJMS

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“…Moreover, isatins are the synthetic precursors of some biologically important compounds 14,15 . Because of the continuing interest about isatin and its derivatives [16][17][18][19] , the present work was undertaken to test the solubility of isatin in different solvents at different temperatures and as a result, to evaluate different thermodynamic parameters. Further, various thermodynamic parameters have been evaluated from these solubility data.…”

Section: Introductionmentioning

confidence: 99%

Solubility of a Pharmacological Intermediate Drug Isatin in Different Solvents at Various Temperatures

Baluja

Bhalodia

Bhatt

et al. 2013

ILCPA

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The solubility of isatin in different solvents was studied by a gravimetrical method from (298.15 to 318.15) K under atmospheric pressure and the solubility data were correlated against temperature. The solvents selected for the present study are: water, methanol, ethanol, 1-butanol, dichloromethane, dichloroethane, chloroform and carbon tetra chloride. Among chlorinated solvents, solubility is observed to be maximum in 1, 2-dichloroethane and minimum in dichloromethane whereas in alcohols, maximum solubility is observed in methanol. In water, solubility is found to be minimum. Further, some thermodynamic parameters such as Gibb's energy (ΔG sol ), heat of solution (ΔH sol ) and entropy of solution (ΔS sol ) have also been evaluated.

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“…[1] They are useful motifs with which to introduce diversity and create large libraries of compounds (for example, in parallel combinatorial chemistry, [2] in dynamic combinatorial chemistry with mixed libraries, [3] in libraries that use chemical-domain shuffling [4] and in combinatorial chemistry in the agrosciences). [5] In organic synthesis, oxime ethers are also interesting building blocks because of the electrophilic oxime moiety and for the potential to undergo rearrangement.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Unusual Oxime Ethers by Reaction of Tetranitromethane with B‐Alkylcatecholboranes

Lüthy

Schenk

Renaud

2010

Chemistry A European J

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The reaction of tetranitromethane with B-alkylcatecholboranes leads to the formation of unusual dinitrooxime ethers. A tentative mechanism is provided, which suggests the involvement of extremely fast addition of alkyl radicals to tetranitromethane. The substitution of one of the nitro groups in the oxime ethers by nucleophiles (such as secondary amines, halogens and styrene) and by radicals generated from B-alkylcatecholboranes is reported.

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Respiratory syncytial virus fusion inhibitors. Part 7: Structure–activity relationships associated with a series of isatin oximes that demonstrate antiviral activity in vivo

Cited by 42 publications

References 22 publications

A Classification Study of Respiratory Syncytial Virus (RSV) Inhibitors by Variable Selection with Random Forest

A Classification Study of Respiratory Syncytial Virus (RSV) Inhibitors by Variable Selection with Random Forest

Solubility of a Pharmacological Intermediate Drug Isatin in Different Solvents at Various Temperatures

Synthesis of Unusual Oxime Ethers by Reaction of Tetranitromethane with B‐Alkylcatecholboranes

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