62102-28-7Relevant academic research and scientific papers
Synthesis and antiviral activity of the carbocyclic analogue of the highly potent and selective anti-VZV bicyclo furano pyrimidines
Migliore, Marco D.,Zonta, Nicola,McGuigan, Christopher,Henson, Geoffrey,Andrei, Graciela,Snoeck, Robert,Balzarini, Jan
, p. 6485 - 6492 (2007)
Carbocyclic nucleoside analogues are catabolically stable since they are resistant to phosphorolytic cleavage by pyrimidine nucleoside phosphorylase enzymes. The carbocyclic analogue (C-BCNA) of the highly potent and selective anti-VZV bicyclic nucleoside
Synthesis of the Carbocyclic Analogue of the Antiviral Nucleoside (E)-5-(2-Bromovinyl)-2'-deoxyuridine
Cookson, Richard C.,Dudfield, Philip J.,Scopes, David I.C.
, p. 399 - 404 (2007/10/02)
The cyclopentanecarboxylic acid (1) was converted via the isocyanate (2) and the urea (5) into carbocyclic uridine (12).Similarly, the α- and β-epimers of carbocyclic 2'-deoxyuridine, (19a) and (19b), were synthesized from the acids (13).Compounds (19a) and (19b) were furhter modified to afford carbocyclic (E)-5-(2-bromovinyl)-2'-deoxyuridine (25b) and its α-epimer (25a), respectively.
Synthesis of cyclopentane analogs of (2'- and 3'-deoxy-erythro-pentofuranosyl and ribofuranosyl)-2-thiouracil nucleosides
Hronowski, Lucjan J. J.,Szarek, Walter A.
, p. 1620 - 1629 (2007/10/02)
Three new carbocyclic analogus of nucleosides having the 2-thiouracil base have been synthesized.The cyclopentyl groups in these nucleosides are (+/-)- (see 31), (+/-)- (see 32) and (+/-)- (see 33).The nucleosides were prepared by coupling the appropriate hydroxy derivatives of cis-3-aminocyclopentanemethanol with 3-ethoxypropenoyl isothiocyanate (21) followed by cyclization in 15 N aqueous ammonia to give the 2-thiouracil nucleosides.In addition a modified and shortenedsynthetic route is described for the synthesys of (+/-)-(1β,2α,3α,4β)-4-amino-2,3-dihydroxy-cyclopentanemethanol (19).The (1)H nmr spectra at 200 MHz of all of the synthetic intermediates, the 2-thiouracil nucleosides, and of the corresponding carbocyclic analogs of uracil nucleosides are discussed.It is shown that each nucleoside has a characteristically unique (1)H nmr spectrum and that in general the protons in the sulfur-containing compounds resonate at lower filds than those in the corresponding oxygen-containing compounds.The magnitude of this downfield shift is inversely related to the number of bonds separating a particular proton from the sulfur atom.
Synthesis and Antiviral Activity of the Carbocyclic Analogues of (E)-5-(2-Halovinyl)-2'-deoxyuridines and (E)-5-(2-Halovinyl)-2'-deoxycytidines
Herdewijn, Piet,Clercq, Erik De,Balzarini, Jan,Vanderhaeghe, Hubert
, p. 550 - 555 (2007/10/02)
The carbocyclic analogues of the potent and selective antiherpes agents (E)-5-(2-bromovinyl)-2'-deoxyuridine (BVDU), (E)-5-(2-iodovinyl)-2'-deoxyuridine (IVDU), and (E)-5-(2-bromovinyl)-2'-deoxycytidine (BVDC) were synthesized by conventional methods with use of carbocyclic 2'-deoxyuridine as starting material.C-BVDU, C-IVDU, and C-BVDC were equally selective, albeit slightly less potent, in their antiherpes action than BVDU, IVDU, and BVDC.Although resistant to degradation by pyrimidine nucleoside phosphorylases, C-BVDU did not prove more effective than BVDU in the systemic (oral, intraperitoneal) or topical treatment of HSV-1 infections in mice.
