- Regioselective C(sp3)-H alkylation of a fructopyranose derivative by 1,6-HAT
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Regioselective C(sp3)-H alkylation of a fructopyranose derivative using electron-deficient alkenes as alkylation reagents was achieved. The reaction proceededvia1,6-hydrogen atom transfer under photoredox iridium catalysis. Several functional g
- Li, Yanru,Miyamoto, Shoto,Torigoe, Takeru,Kuninobu, Yoichiro
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supporting information
p. 3124 - 3127
(2021/04/21)
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- The first general protocol for N-monoalkylation of sulfamate esters: Benign synthesis of N-alkyl Topiramate (anticonvulsant drug) derivatives
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A novel protocol for the highly selective N-monoalkylation of the sulfamate ester moiety has been developed. This reaction proceeded efficiently using alkyl halides, benzyl halides and -halo ketones as the electrophile in the presence of KF-Al2O3 as a cost-effective and robust catalyst. This approach provides new access to N-monoalkylated Topiramate (anticonvulsant drug) derivatives which are potentially of great importance in medicinal chemistry.
- Saeidian, Hamid,Abdoli, Morteza
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p. 463 - 470
(2015/10/19)
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- Anticonvulsant O-Alkyl Sulfamates. 2,3:4,5-Bis-O-(1-methylethylidene)-β-D-fructopyranose Sulfamate and Related Compounds.
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Novel sugar sulfamate 1 (McN-4853, topiramate) has been found to exhibit potent anticonvulsant activity analogous to that of phenytoin.In the maximal electroshock seizure test, orally at 2 h in mice, 1 had an ED50 of 39 mg/kg.Orally, 1 had a duration of action in excess of 8 h.Other aspects of the pharmacology of 1, as well as neurochemistry and carbonic anhydrase inhibition, are discussed.The conformational behavior of 1 in solution and in the solid state are discussed.A series of analogues of 1 were synthesized and examined for anticonvulsant properties.
- Maryanoff, Bruce E.,Nortey, Samuel O.,Gardocki, Joseph F.,Shank, Richard P.,Dodgson, Susanna P.
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p. 880 - 887
(2007/10/02)
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