Alkylating nucleosides. 2. Synthesis and cytostatic activity of bromomethylpyrazole and pyrazole nitrogen mustard nucleosides
Тип публикации: Journal Article
Дата публикации: 1979-07-01
scimago Q1
wos Q1
БС1
SJR: 1.801
CiteScore: 11.5
Impact factor: 6.8
ISSN: 00222623, 15204804
PubMed ID:
448680
Drug Discovery
Molecular Medicine
Краткое описание
Glycosylation of ethyl 3(5)-(bromomethyl)pyrazole-5(3)-carboxylate (3) and 3(5)-(bromomethyl)pyrazole-5(3)-carboxamide (4) with poly-O-acetylated sugars via an acid-catalyzed fusion method afforded the corresponding ethyl 3-(bromomethyl)pyrazole-5-carboxylate and 3-(bromomethyl)pyrazole-5-carboxamide substituted nucleosides 5 and 7, respectively. In some cases, the positional isomers 6 and 8 were also obtained. Treatment of 5 and 7 with methanolic ammonia gave the deprotected 3-(aminomethyl)pyrazole-5-carboxamide nucleosides 9. Reaction of 3--5 and 7 with bis(2-chloroethyl)amine led to the corresponding pyrazole nitrogen mustards 10--13. All the bromomethylpyrazole nucleosides described showed significant cytostatic activity against HeLa cell cultures.
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García López M. T., HERRANZ R., Alonso G. Alkylating nucleosides. 2. Synthesis and cytostatic activity of bromomethylpyrazole and pyrazole nitrogen mustard nucleosides // Journal of Medicinal Chemistry. 1979. Vol. 22. No. 7. pp. 807-811.
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García López M. T., HERRANZ R., Alonso G. Alkylating nucleosides. 2. Synthesis and cytostatic activity of bromomethylpyrazole and pyrazole nitrogen mustard nucleosides // Journal of Medicinal Chemistry. 1979. Vol. 22. No. 7. pp. 807-811.
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TY - JOUR
DO - 10.1021/jm00193a011
UR - https://doi.org/10.1021/jm00193a011
TI - Alkylating nucleosides. 2. Synthesis and cytostatic activity of bromomethylpyrazole and pyrazole nitrogen mustard nucleosides
T2 - Journal of Medicinal Chemistry
AU - García López, M Teresa
AU - HERRANZ, Rosario
AU - Alonso, Gregorio
PY - 1979
DA - 1979/07/01
PB - American Chemical Society (ACS)
SP - 807-811
IS - 7
VL - 22
PMID - 448680
SN - 0022-2623
SN - 1520-4804
ER -
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@article{1979_García López,
author = {M Teresa García López and Rosario HERRANZ and Gregorio Alonso},
title = {Alkylating nucleosides. 2. Synthesis and cytostatic activity of bromomethylpyrazole and pyrazole nitrogen mustard nucleosides},
journal = {Journal of Medicinal Chemistry},
year = {1979},
volume = {22},
publisher = {American Chemical Society (ACS)},
month = {jul},
url = {https://doi.org/10.1021/jm00193a011},
number = {7},
pages = {807--811},
doi = {10.1021/jm00193a011}
}
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García López, M. Teresa, et al. “Alkylating nucleosides. 2. Synthesis and cytostatic activity of bromomethylpyrazole and pyrazole nitrogen mustard nucleosides.” Journal of Medicinal Chemistry, vol. 22, no. 7, Jul. 1979, pp. 807-811. https://doi.org/10.1021/jm00193a011.