30516-06-4Relevant academic research and scientific papers
4-Benzyloxy-γ-sultone derivatives: Discovery of a novel family of non-nucleoside inhibitors of human cytomegalovirus and varicella zoster virus
De Castro, Sonia,García-Aparicio, Carlos,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan,Camarasa, María-José,Velázquez, Sonsoles
experimental part, p. 1582 - 1591 (2010/01/07)
We report the synthesis and antiviral activity of a new family of non-nucleoside antivirals, derived from the 4-keto-1,2-oxathiole-2,2-dioxide (β-keto-γ-sultone) heterocyclic system. Several 4- and 5-substituted-5H-1,2-oxathiole-2,2-dioxide derivatives were found to have a selective inhibitory activity against human cytomegalovirus (HCMV) and varicella zoster virus (VZV) replication in vitro, being inactive against a variety of other DNA and RNA viruses. A structure-activity relationship (SAR) study showed that the presence of a benzyl at the 5 position and a benzyloxy substituent at the 4 position are a prerequisite for anti-HCMV and VZV activity. The novel compounds do not show cross-resistance against a wide variety of mutant drug-resistant HCMV strains, pointing to a novel mechanism of antiviral action.
Studies into the synthesis of derivatives of 4-amino-2,3-dihydroisothiazole 1,1-dioxides and 4-amino-1,2-oxathiole 2,2-dioxides, the search for linked π-system containing analogues as potential inhibitors of HIV-1 reverse transcriptase
Ingate, Simon T.,Marco, Jose L.,Witvrouw, Myriam,Pannecouque, Cristophe,De Clercq, Erik
, p. 17795 - 17814 (2007/10/03)
The synthesis, and anti HIV-1 activity, of new derivatives of 4-amino-1,2-oxathiole 2,2-dioxide (3, 5, 6 and 9) and 4-amino-2,3-dihydroisothiazole 1,1-dioxide (14), a new heterocyclic ring system, is described.
KINETIC RESOLUTION OF KETONE CYANOHYDRIN ACETATES WITH A MICROBIAL ENZYME
Ohta, Hiromichi,Kimura,Yoichi,Sugano, Yasushi
, p. 6957 - 6960 (2007/10/02)
Incubation of dl-1-cyano-1-metylalkyl (or alkenyl) acatates (methyl ketone cyanohydrin acetates) with cells of Pichia miso IAM 4682 afforded optically active acetates and the corresponding ketones via asymmetric hydrolysis.Resulting (S)-2-cyano-2-undecyl acetate was converted to the aminofuranone derivative without losing its optical purity.
Oxidative Decyanation of Secondary Nitriles to Ketones
Freerksen, Robert W.,Selikson, Sandra J.,Wroble, Randall R.,Kyler, S. Keith,Watt, David S.
, p. 4087 - 4096 (2007/10/02)
Procedures for the oxidative decyanation of secondary nitriles to ketones involve (1) iodination of N-(trialkylsilyl)ketenimines derived from secondary nitriles and subsequent hydrolysis of the α-iodo nitriles with silver oxide, (2) addition of nitrosobenzene to N-(trialkylsilyl)ketenimines, (3) conversion of secondary nitriles to α-(phenylthio) nitriles and subsequent hydrolysis with N-bromosuccinimide in aqueous acetonitrile, and (4) preparation of α-hydroperoxy nitriles by direct oxygenation of anions of secondary nitriles and subsequent reductive hydrolysis with stannous chloride followed by sodium hydroxide.The latter general procedure was applied to various secondary nitriles bearing dialkyl, aryl and alkyl, and diaryl substituents to provide ketones in good yield and was extended to the oxidative decyanation of α,β-unsaturated nitriles to furnish α,β-unsaturated ketones.
