1992
DOI: 10.1016/0166-3542(92)90053-8
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Improved synthesis and biological evaluation of an acyclic thiosangivamycin active against human cytomegalovirus

Abstract: We previously described the synthesis and in vitro antiviral activity of an acyclic thiosangivamycin analog (Gupta et al., 1989a). In order to extend these initial studies, a new, multi-gram synthesis of 4-amino-7-[(2-hydroxy- ethoxy)methyl]pyrrolo]2,3-d]pyrimidine-5-thiocarboxamide (compound 229) was achieved in 5 steps from the known 5-amino-2-bromo-3,4-dicyanopyrrole in good overall yield. In plaque reduction assays with HCMV, compound 229 had an IC50 of 7 microM; in yield reduction assays the IC90 was 25 m… Show more

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Cited by 14 publications
(14 citation statements)
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“…= 17.5 Hz), 5.88 (ddd, 1H, H-3', J3•? = 19.7 Hz), 5.38 (ddd, 1H, H-2', J?? = 52.1 Hz), 4.76 (ddd, 2H, H-5'ab), 4.41 (m, 3H, H-4', CH2), 1.41 (t, 3H, CH3).…”
Section: Methodsmentioning
confidence: 99%
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“…= 17.5 Hz), 5.88 (ddd, 1H, H-3', J3•? = 19.7 Hz), 5.38 (ddd, 1H, H-2', J?? = 52.1 Hz), 4.76 (ddd, 2H, H-5'ab), 4.41 (m, 3H, H-4', CH2), 1.41 (t, 3H, CH3).…”
Section: Methodsmentioning
confidence: 99%
“…Hz, Jv F = 13.3 Hz), 5.94 (d, 1H, 3'-OH), 5.17 (ddd, 1H, H-2', J2• F = 52.7 Hz), 5.11 (t, 1H, 5'-OH), 4.36 (ddd, 1H, H-3', «73-f = 18.7 Hz), 3.84 (m, 1H, H-4'), 3.66 (m, 2H, H-5'ab); UV Amax (nm) (log <?) methanol, 278 (4.23), 229 (4.08), 208 (4.32); pH 1, 272 (4.12), 232 (4.24), 205 (4.11); pH 11,277 (4.23), 231 (4.05); IR (KBr) 2223 cm-1 (cyano); TLC Rf -0.57, solvent system C. Anal.…”
Section: °C;mentioning
confidence: 99%
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“…132 Acyclic analogues of 7-deazapurine nucleosides and nucleotides were also screened for antiviral activities but generally these compounds showed only poor activities, especially when compared with the corresponding purine analogues. [153][154][155][156] Nevertheless, some acyclic analogues of 7-bromo-7-deazaadenosine (81a-b) [157][158][159] and thiosangivamycin (82a-b) [160][161][162][163] possess selective activity against human cytomegalovirus that is comparable or better than that of ganciclovir.…”
Section: Nucleosides With Antiviral Activities Against Other Virusesmentioning
confidence: 99%
“…As part of our ongoing research involving pyrrolo [2,3-d]pyrimidines as potential antiviral agents (3,17,34,40,(45)(46)(47), we have described the synthesis and activities against HCMV of a number of nonnucleoside derivatives related to toyocamycin, sangivamycin, and thiosangivamycin (35). The studies in this area have been expanded, and a description of the structureactivity relationships of this class of compounds has been reported (37,38).…”
mentioning
confidence: 99%