13199-25-2Relevant articles and documents
Thioimidate N-oxides: From nature to synthetic pathways
Schleiss, Julie,Cerniauskaite, Deimante,Gueyrard, David,Iori, Renato,Rollin, Patrick,Tatibou?t, Arnaud
, p. 725 - 728 (2010)
Inspired by the unexpected reactivity of desulfated naturally occurring glucoraphenin, methods to synthesize thioimidate N-oxides (TIO) have been devised on simple or carbohydrate templates. Either through halocyclization or under Mitsunobu conditions, the starting thiohydroximates cyclized to generate efficiently the corresponding TIO. Georg Thieme Verlag Stuttgart ? New York.
First total synthesis and structure confirmation of diacetylenic polyol (+)-oploxyne B
Srihari,Sathish Reddy,Yadav,Yedlapudi,Kalivendi, Shasi V.
supporting information, p. 5616 - 5618 (2013/09/23)
The first total synthesis of the natural product (+)-oploxyne B is achieved. The synthesis has led to the confirmation of absolute stereochemistry of the natural product. The natural product displayed cytotoxic activity with IC50 values varying
Stereoselective total synthesis of goniothalesdiol A via chiron approach
Yadav, Jhillu S.,Nageshwar Rao, Ragam,Somaiah, Ragam,Harikrishna, Valaboju,Subba Reddy, Basi V.
experimental part, p. 1362 - 1368 (2010/09/20)
The stereocontrolled synthesis of goniothalesdiol A, a dihydroxylated tetrahydropyran compound, has been accomplished using d-ribose as chiral precursor. The key steps involved are aryl Grignard reaction, stereoselective alkoxy-directed keto reduction, and intramolecular oxy-Michael addition.
Synthesis of the proposed structure of queenslandon
Navickas, Vaidotas,Maier, Martin E.
scheme or table, p. 94 - 101 (2010/03/03)
The proposed structure of the benzolactone queenslandon (6) was synthesized utilizing a triol containing building block prepared from d-ribose. While a ring-closing metathesis approach did not lead to the macrocycle, alkylation of a benzyl(phenyl)selane, elimination to generate the styrene double bond, followed by Mitsunobu macrolactonization proved to be successful. Spectral data suggest that the structure of queenslandon should be revised, probably to the C11 epimer.
Synthesis and l-fucosidase inhibitory activity of a new series of cyclic sugar imines-in situ formation and assay of their saturated counterparts
Behr, Jean-Bernard
scheme or table, p. 4498 - 4501 (2009/11/30)
The synthesis of a series of aryl-substituted cyclic sugar imines was performed via a tandem nucleophilic addition/substitution reaction. The so-obtained ketimines displayed fucosidase inhibitory activities (IC50 = 46-556 μM). Their reduced counterparts were prepared and assayed after addition of sodium borohydride to the enzymatic assay stock solution. The pyrrolidines strongly inhibit fucosidase (IC50 = 0.65-150 μM).
Synthesis of C-ribosyl imidazo[2,1-f][1,2,4]triazines as inhibitors of adenosine and AMP deaminases
Dudfield, Philip J.,Le, Van-Due,Lindell, Stephen D.,Rees, Charles W.
, p. 2929 - 2936 (2007/10/03)
The 3-β-D-ribofuranoside 6 of the new imidazo[2,1-f][1,2,4]triazine 27 is isomeric and isoelectronic with the nucleoside deaminoformycin 1 which is a good inhibitor of adenosine deaminase (ADA) while its 5′-monophosphate 2 is a good inhibitor of adenosine 5′-monophosphate deaminase (AMPDA). The 6-methylsulfanyl derivative 7 of 6 is synthesized by condensation of the monocyclic 1,2,4-triazine 9 with bromo aldehyde 10, which is accompanied by cyclization to give the protected C-nucleoside 21; the 8-methylsulfanyl group of 21 is removed by replacement by hydrazine and oxidation. The 1,2,4-triazine 9 cyclizes similarly with chloroacetaldehyde or its dimethyl acetal to give 6,8-bis(methylsulfanyl)imidazo[2,1-f][1,2,4]triazine 17, which is converted into the parent heterocycle 27 by two routes, and into mono- and di-substituted derivatives (19, 20, 24, 25, 28-30) of the new ring system. Riboside 7 is an inhibitor of mammalian ADA (IC50 40 μM). The Royal Society of Chemistry 1999.
