Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties
Apstrakt
3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2-benzamido (15) and 3-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.
Ključne reči:
C-nucleosides / pyrazoles / tetrazoles / cytotoxic activity / antiviral activity / 2,5-anhydro sugars / X-ray crystallographyIzvor:
Tetrahedron, 2002, 58, 3, 569-580
DOI: 10.1016/S0040-4020(01)01126-7
ISSN: 0040-4020
WoS: 000173338300012
Scopus: 2-s2.0-0037074195
Kolekcije
Institucija/grupa
VinčaTY - JOUR AU - Popsavin, M AU - Torovic, L AU - Spaic, S AU - Stankov, S AU - Kapor, Agneš AU - Tomić, Zoran D. AU - Popsavin, V PY - 2002 UR - https://vinar.vin.bg.ac.rs/handle/123456789/2494 AB - 3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2-benzamido (15) and 3-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved. T2 - Tetrahedron T1 - Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties VL - 58 IS - 3 SP - 569 EP - 580 DO - 10.1016/S0040-4020(01)01126-7 ER -
@article{ author = "Popsavin, M and Torovic, L and Spaic, S and Stankov, S and Kapor, Agneš and Tomić, Zoran D. and Popsavin, V", year = "2002", abstract = "3(5)-Carboxamido-4-(beta-D-ribofuranosyl)pyrazoles bearing 2-benzamido (15) and 3-mesyloxy (29) isosteric groups, as well as the tetrazole C-nucleosides with 2-benzamido-2-deoxy-beta-D-ribofuranose (19) and 3-azido-3-deoxy-beta-D-xylofuranose (36) as sugar segments, have been synthesized starting from D-glucose, by utilizing the 2,5-anhydro-D-glucose ethylene acetal derivatives 1 and 20 as divergent intermediates. The C-nucleosides 15 and 36 were shown to be moderate inhibitors of the in vitro growth of both N2a and BHK 21 tumour cell lines, whereas 29 showed a selective, although not potent cytotoxic activity against N2a cells. Compound 29 also showed a moderate in vitro antiviral activity towards the rabies virus. (C) 2002 Elsevier Science Ltd. All rights reserved.", journal = "Tetrahedron", title = "Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties", volume = "58", number = "3", pages = "569-580", doi = "10.1016/S0040-4020(01)01126-7" }
Popsavin, M., Torovic, L., Spaic, S., Stankov, S., Kapor, A., Tomić, Z. D.,& Popsavin, V.. (2002). Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties. in Tetrahedron, 58(3), 569-580. https://doi.org/10.1016/S0040-4020(01)01126-7
Popsavin M, Torovic L, Spaic S, Stankov S, Kapor A, Tomić ZD, Popsavin V. Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties. in Tetrahedron. 2002;58(3):569-580. doi:10.1016/S0040-4020(01)01126-7 .
Popsavin, M, Torovic, L, Spaic, S, Stankov, S, Kapor, Agneš, Tomić, Zoran D., Popsavin, V, "Synthesis and biological evaluation of new pyrazole- and tetrazole-related C-nucleosides with modified sugar moieties" in Tetrahedron, 58, no. 3 (2002):569-580, https://doi.org/10.1016/S0040-4020(01)01126-7 . .