Structure–activity relationships for osteolathyrism. III. Substituted thiosemicarbazides

Dawson, Douglas A.; Schultz, T.W.; Baker, Leslie L.; Mannar, A

doi:10.1002/jat.2550100111

Cited by 24 publications

(3 citation statements)

References 14 publications

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“…Biological activities of thiosemicarbazides and thiosemicarbazones are generally associated with their metal chelating ability. , A relationship between the structure of certain thiosemicarbazide derivatives and their biological activity was established . The effect of the substitution of various groups at different positions of the thiosemicarbazide moiety as well as its conformational structure on antiviral activity was explored. ,− The review of the structures of ca.…”

Section: Introductionmentioning

confidence: 99%

Photochemical Isomerizations of Thiosemicarbazide, a Matrix Isolation Study

et al. 2012

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Two thione conformers of monomeric thiosemicarbazide were trapped from the gas phase into a low-temperature Ar matrix. A phototransformation converting the less stable form of the compound into the most stable conformer was induced by irradiation with near-IR (λ = 1462 nm) or UV (λ > 320 nm) light. This photoeffect allowed separation of the IR spectra of the observed thione forms. The structures of both observed isomers were identified by comparison of the separated experimental IR spectra with the spectra theoretically predicted for two most stable forms of the compound. The population ratio of the two conformers in an Ar matrix, prior to any irradiation, was estimated to be equal ≈2:1. Irradiation of matrix-isolated thiosemicarbazide with shorter-wavelength UV (λ > 270 nm) light induced a phototautomeric reaction generating thiol forms of the compound.

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Section: Introductionmentioning

confidence: 99%

Photochemical Isomerizations of Thiosemicarbazide, a Matrix Isolation Study

et al. 2012

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“…It has been demonstrated that the molecular substructure H 2 N‐NH‐C(=O) is a necessary fragment for osteolathyrism induction [60]. The effect of molecular structure on the development of frog embryos was further studied for a series of eight alkyl‐substituted acid hydrazides [61] and eight thiosemicarbazides [62], and 10 benzoic acid hydrazides and alkyl carbazates [63]. Although insufficient data exist to confirm the supposition, it is highly probable that the same effects that were observed in this ecologically relevant species would also be found in human‐surrogate species.…”

Section: Introductionmentioning

confidence: 99%

“…The latter analysis was successful in identifying structural fragments that could be related mechanistically to developmental toxicity effects. Other QSAR approaches to predicting developmental toxicity effects include dynamic QSAR of 36 semicarbazides and thiosemicarbazides reported by Schultz and coworkers [60–63]. This approach considers different conformers, and QSARs were developed using electron acceptor properties [66].…”

Section: Introductionmentioning

confidence: 99%

Quantitative structure-activity relationships for human health effects: Commonalities with other endpoints

Cronin

Dearden

Walker

et al. 2003

Environmental Toxicology and Chemistry

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Abstract-This article describes the use of quantitative structure-activity relationships (QSARs) to predict toxicity endpoints for ecologically relevant and human-surrogate species. The interrelationships between the endpoints, and the possibilities of exploring the commonalities of chemical action from one species to another as well as from one endpoint to another, are evaluated. A number of toxic endpoints are discussed including mutagenicity and carcinogenicity; developmental toxicity (teratogenicity); acute toxicity; skin sensitization; skin, eye, and sensory irritation; and the modeling of membrane permeability. A number of electrophilic molecular substructures have been identified that are common to a number of toxicities. It is postulated that if such a substructure is observed in a molecule, it may exhibit a range of toxicities. Further, there appear to be relationships between the toxicity to ecologically relevant and human-surrogate species, which may allow for appreciation and possible extrapolation in both directions. Overall, however, QSARs are limited by the paucity of available toxicological data and information.

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