117641-39-1Relevant articles and documents
Synthesis of [13C4]Baraclude (entecavir)
Tran, Scott B.,Ekhato, Ihoezo V.,Rinehart, J. Kent
scheme or table, p. 485 - 489 (2010/07/04)
Entecavir, labeled as 1H-[13C4]purin-6(9H)-one, was prepared from commercially available [13C]guanidine HCl, 1 and diethyl [1,2,3-13C3]malonate, 2. The reagents were condensed together to give 2-amino-4,6-dichloro[2,4,5,6-13C 4]pyrimidine 3, which in turn was coupled to an optically active amino cyclopentanol derivative, 9. A further sequence of eight reaction steps completed the constructions of the purine ring system and the exocyclic olefin attachment on the cyclic pentyl portion, 18. The removal of the methoxide and benzyl protecting groups gave [13C4]entecavir, 20 in an overall yield of 6.8%. The chemical purity of the title compound was determined by HPLC to be 99.23%. The percent isotopic [13C4] abundance was found by mass spectral analysis to be 96.7%. No detectable level of the unlabeled entecavir was found by LC-MS analysis. Copyright
Novel 3′-deoxy analogs of the anti-HBV agent entecavir: Synthesis of enantiomers from a single chiral epoxide
Ruediger, Edward,Martel, Alain,Meanwell, Nicholas,Solomon, Carola,Turmel, Brigitte
, p. 739 - 742 (2007/10/03)
A synthesis of novel 3′-deoxy analogs of the anti-HBV agent entecavir (BMS-200475) was devised using regioselective ring opening of suitable cyclopentene epoxides as the key step. This versatile approach afforded access to an enantiomeric pair of carbocyclic nucleosides from a single chiral intermediate.
New convergent synthesis of carbocyclic nucleoside analogues
Ludek, Olaf R.,Meier, Chris
, p. 2101 - 2109 (2007/10/03)
Two convergent approaches towards the synthesis of carbocyclic nucleoside analogs will be described. Both approaches start from the stereochemically pure cyclopentenol 8 that has been prepared enantioselectively from an alkylated cyclopentadiene. Using these approaches, carbocyclic analogues of dT, FdU and BVdU have been prepared. Moreover, the conversion into the cycloSalpronucleotide and the corresponding nucleotide will be presented for one example.
BMS-200475, a novel carbocyclic 2'-deoxyguanosine analog with potent and selective anti-hepatitis B virus activity in vitro
Bisacchi,Chao,Bachard,Daris,Innaimo,Jacobs,Kocy,Lapointe,Martel,Merchant,Slusarchyk,Sundeen,Young,Colonno,Zahler
, p. 127 - 132 (2007/10/03)
BMS-200475, a never carbocyclic analog of 2'-deoxyguanosine, is a potent inhibitor of hepatitis B virus in vitro (ED50 = 3 nM) with relatively low cytotoxicity (CC50 = 21-120 μM). A practical 10-step asymmetric synthesis was developed affording BMS-200475 in 18% overall chemical yield and > 99% optical purity. The enantiomer of BMS-200475 as well as the adenine, thymine, and iodouracil analogs are much less active.
Hydroxymethyl (methylenecyclopentyl) purines and pyrimidines
-
, (2008/06/13)
Antiviral activity is exhibited by compounds having the formula STR1 and its pharmaceutically acceptable salts.
Use of Diethylaminosulphur Trifluoride (DAST) in the Preparation of Synthons of Carbocyclic Nucleosides
Biggadike, Keith,Borthwick, Alan D.,Evans, Derek,Exall, Anne M.,Kirk, Barrie E.,et al.
, p. 549 - 554 (2007/10/02)
Diethylaminosulphur trifluoride (DAST) converted the protected amino triol (4) into the fluorine-containing compounds (8) and (10).The same reagent converted the alcohol (9) into compounds (10), (5), and (11) and transformed the azido alcohol (15) into the fluoroazides (16) and (19).The fluorinated compounds (5), (8), and (16) are useful synthons for fluorocarbocyclic nucleosides.The effect of neighbouring groups on the course of some DAST reactions is discussed.
