Synthesis and reactions of 2-methyl-5-(d-arabino-tetra-hydroxybutyl)-3-pyrrolecarbohydrazide

Sadek, M.; Abdel-Baky, Samy; Soccary, Nagwa N. El

doi:10.1016/0008-6215(92)80030-5

Cited by 3 publications

(2 citation statements)

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“…Ethyl 5-(1,2,3,4-tetrahydroxybutyl)-2-methylfuran-3-carboxylate ( 1 ) [ 34 ] was prepared, then boiled with hydrazine hydrate to give carbohydrazide 2 [ 35 ], which when condensed with a variety of ketones afforded carbohydrazides 3 – 6 in 64–96% yield ( Scheme 1 ).…”

Section: Resultsmentioning

confidence: 99%

“…1,3,4-Thiadiazoles are thus a group of heterocycles whose derivatives are important in industry, medicine and agriculture [ 13 , 15 , 16 , 17 , 18 , 19 , 20 , 21 ]. Accordingly, in continuation of our work in this area [ 22 , 23 , 24 , 25 , 26 , 27 ], a variety of heterocyclic derivatives have been prepared from saccharide derivatives, involving some new thiadiazoles, oxathiadiazoles, and their chemistry and effect of the derivatives on the enzyme tyrosinase was studied [ 28 , 29 , 30 , 31 ], which is the rate limiting step in melanin biosynthesis [ 32 ]. In humans, the main role of the melanins is photoprotection of the skin by absorbing UV radiation that causes DNA damage and the formation of reactive oxygen species (ROS).…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of New 1,3,4-Thiadiazole and 1,2,3,4-Oxathiadiazole Derivatives from Carbohydrate Precursors and Study of Their Effect on Tyrosinase Enzyme

et al. 2012

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5-(1,2,3,4-Tetrahydroxybutyl)-2-methylfuran-3-carbohydrazide (2) was condensed with a variety of ketones to afford carbohydrazide derivatives 3–6. Acetylation of 3–5 afforded the acetyl derivatives 7–9, while periodate oxidation of 3–6 afforded the formyl derivatives 10–13. Acid catalyzed condensation of thiosemicarbazide or o-tolylthiosemicarbazide with the prepared aldehydes 10–12 gave thiosemicarbazone derivatives 14–19. Cyclization of the latter with acetic anhydride afforded 4,5-dihydro-1,3,4-thiadiazolyl derivatives 20–25. On the other hand, condensation of p-tosylhydrazine with the prepared aldehydes 10–12 afforded p-tosylhydrazone derivatives 26–28. Cyclization of 26–28 with acetic anhydride afforded 1,2,3,4-oxathiadiazole derivatives 29–31 respectively. Moreover, the obtained results regarding to the effect of some of the prepared compounds on tyrosinase enzyme showed that the majority of these compounds having an inhibitory effect; especially compounds 12, 16, 17, and 28.

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Section: Resultsmentioning

confidence: 99%