Thermolysis of the sodium salt of tricarbonyl(acetophenone)chromium <i>p</i>-tosylhydrazone

Ashraf, Muhammad

doi:10.1139/v76-061

Cited by 9 publications

(1 citation statement)

References 11 publications

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“…In the literature, it was described in 1976 the synthesis of acetophenone p-tosylhydrazone without catalyst for 5.5 hours with 68% yield (Ashraf, 1976); the synthesis using benzaldehyde salicylic acid hydrazide and 4-dimethylaminobenzaldehyde or 4nitrobenzaldehyde for 4 hours (Al-Ajrawy, 2011). To enhance the reaction, we used during our work in the synthesis of the salicylhydrazones (GSn) and p-tosylhydrazones (GTn) the glacial acetic acidic and technical ethanol.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and trypanocidal activity of salicylhydrazones and p-tosylhydrazones of S-(+)-carvone and arylketones on African trypanosomiasis

Glinma¹,

Gbaguidi²,

Kasséhin³

et al. 2015

J App Pharm Sci

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Hydrazones are nowadays considered to be good candidates for various pharmaceutical applications. Here, we have synthesized two series of hydrazones: salicylhydrazones (GS1-4) and p-tosylhydrazones (GT1-4) from S-(+)-carvone and three aryketones with good yields (57-91%). Molecules were characterized by elemental analyses; TLC, NMR 1 H, NMR 13 C and MS. Submitted, in vitro, to their antiparasitic testing on Trypanosoma brucei brucei, and toxicity on Artemia salina Leach, all compounds except GT2 showed significant antitrypanosomal activity IC50 ranging from 1 to 34 micromolar (µM). Among them, 2-acetynaphthalene salicylhydrazone GS4 (IC50 = 1.97 ± 0.42 µM) and 7-methoxy-1-tetralone p-tosylhydrazone GT3 (IC50 =7.98 ± 1.65 µM) exhibited good trypanocidal activity and the other are moderates on parasite; when the compounds GS1, GT3 and GT4 presented toxic activity on larvae. In agreement to their selectivity index, which is greater than 1 (SI > 1), products turn out quite selective on the parasite: a series of salicylhydrazones revealed more selective (SI ≥ 11), especially GS4 (SI = 157) than the series of p-tosylhydrazones showed 1 ≤ SI ≤ 22. The synthesized compounds clearly displayed significant selective pharmaceutical activities on the parasite tested.Compounds developing could open promising route to news drug-candidates.

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Section: Resultsmentioning

confidence: 99%

Synthesis and trypanocidal activity of salicylhydrazones and p-tosylhydrazones of S-(+)-carvone and arylketones on African trypanosomiasis

Glinma¹,

Gbaguidi²,

Kasséhin³

et al. 2015

J App Pharm Sci

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ChemInform Abstract: THERMOLYSIS OF THE SODIUM SALT OF TRICARBONYL(ACETOPHENONE)CHROMIUM P‐TOSYLHYDRAZONE

Ashraf¹

1976

Chemischer Informationsdienst

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Controlled Release of Volatile Aldehydes and Ketones from Dynamic Mixtures Generated by Reversible Hydrazone Formation

Levrand¹,

Fieber²,

Lehn³

et al. 2007

Helvetica Chimica Acta

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Delivery systems generated by reversible hydrazone formation from hydrazine derivatives (see Fig. 1) and carbonyl compounds in H 2 O efficiently increase the long-lastingness of volatile aldehydes and ketones (R 1 R 2 C¼O) in various perfumery applications. The hydrazones are usually obtained in an (E) configuration at the imine double bond (NHN¼C) and, in the case of aliphatic acylhydrazones R'COÀNHÀN¼CR 1 R 2 (R' ¼ alkyl), as syn and anti conformers with respect to the amide bond (COÀNHN). An average free-energy barrier of ca. 78 kJ/mol was determined for the amide-bond rotation by variable-temperature 1 H-NMR measurements ( Fig. 2). In the presence of H 2 O, the hydrazone formation is entirely reversible, reaching an equilibrium composed of the hydrazine derivative, the carbonyl compound, and the corresponding hydrazone. Kinetic measurements carried out by UV/VIS spectroscopy showed that the same equilibrium was reached for the formation and hydrolysis of the hydrazone. Rate constants are strongly pH-dependent and increase with decreasing pH ( Table 1). The influence of the hydrazine structure on the rate constants is less pronounced than the pH effect, and the presence of surfactants reduces the rate of equilibration (Tables 1 and 3). The full reversibility of the hydrazone formation allows to prepare dynamic mixtures by simple addition of a hydrazine derivative to several carbonyl compounds. Dynamic headspace analysis on dry cotton showed that the presence of a hydrazine derivative significantly increased the headspace concentrations of the different carbonyl compounds as compared to the reference sample without hydrazine ( Table 4). The release of the volatiles was found to be efficient for fragrances with high vapor pressures and low H 2 O solubility. Furthermore, a special long-lasting effect was obtained for the release of ketones. The simplicity of generating dynamic mixtures combined with the high efficiency for the release of volatiles makes these systems particularly interesting for practical applications and will certainly influence the development of delivery systems in other areas such as the pharmaceutical or agrochemical industry.

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Thermolysis of the sodium salt of tricarbonyl(acetophenone)chromium p-tosylhydrazone

Cited by 9 publications

References 11 publications

Synthesis and trypanocidal activity of salicylhydrazones and p-tosylhydrazones of S-(+)-carvone and arylketones on African trypanosomiasis

Synthesis and trypanocidal activity of salicylhydrazones and p-tosylhydrazones of S-(+)-carvone and arylketones on African trypanosomiasis

ChemInform Abstract: THERMOLYSIS OF THE SODIUM SALT OF TRICARBONYL(ACETOPHENONE)CHROMIUM P‐TOSYLHYDRAZONE

Controlled Release of Volatile Aldehydes and Ketones from Dynamic Mixtures Generated by Reversible Hydrazone Formation

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