Synthesis of 13-acylamino-huprines: different behavior of diastereomeric 13-methanesulfonamido-huprines on PPA-mediated hydrolysis
Тип публикации: Journal Article
Дата публикации: 2004-06-01
SCImago Q3
WOS Q3
БС2
SJR: 0.36
CiteScore: 3.7
Impact factor: 2.1
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Краткое описание
Two diastereomeric pairs of rationally designed huprines additionally substituted at position 13 with a formamido or an acetamido group have been synthesized as potential high affinity acetylcholinesterase inhibitors. The synthetic sequence involves hydrolysis of two diastereomeric 13-methanesulfonamido-huprines, followed by acylation of the resulting diastereomeric amines. In the hydrolysis reaction, carried out with PPA under harsh conditions, significant amounts of cyclized or rearranged by-products were also formed, depending on the stereochemistry of the starting compound.
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Camps P., G??mez E., Muñoz-Torrero D. Synthesis of 13-acylamino-huprines: different behavior of diastereomeric 13-methanesulfonamido-huprines on PPA-mediated hydrolysis // Tetrahedron. 2004. Vol. 60. No. 25. pp. 5423-5431.
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Camps P., G??mez E., Muñoz-Torrero D. Synthesis of 13-acylamino-huprines: different behavior of diastereomeric 13-methanesulfonamido-huprines on PPA-mediated hydrolysis // Tetrahedron. 2004. Vol. 60. No. 25. pp. 5423-5431.
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TY - JOUR
DO - 10.1016/j.tet.2004.04.054
UR - https://doi.org/10.1016/j.tet.2004.04.054
TI - Synthesis of 13-acylamino-huprines: different behavior of diastereomeric 13-methanesulfonamido-huprines on PPA-mediated hydrolysis
T2 - Tetrahedron
AU - Camps, Pelayo
AU - G??mez, Elena
AU - Muñoz-Torrero, Diego
PY - 2004
DA - 2004/06/01
PB - Elsevier
SP - 5423-5431
IS - 25
VL - 60
SN - 0040-4020
SN - 1464-5416
ER -
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@article{2004_Camps,
author = {Pelayo Camps and Elena G??mez and Diego Muñoz-Torrero},
title = {Synthesis of 13-acylamino-huprines: different behavior of diastereomeric 13-methanesulfonamido-huprines on PPA-mediated hydrolysis},
journal = {Tetrahedron},
year = {2004},
volume = {60},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/j.tet.2004.04.054},
number = {25},
pages = {5423--5431},
doi = {10.1016/j.tet.2004.04.054}
}
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Camps, Pelayo, et al. “Synthesis of 13-acylamino-huprines: different behavior of diastereomeric 13-methanesulfonamido-huprines on PPA-mediated hydrolysis.” Tetrahedron, vol. 60, no. 25, Jun. 2004, pp. 5423-5431. https://doi.org/10.1016/j.tet.2004.04.054.
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