Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
Synthesis of a new class of bisheterocycles via the Heck reaction of eudesmane type methylene lactones with 8-bromoxanthines. / Patrushev, Sergey S.; Rybalova, Tatyana V.; Ivanov, Igor D. и др.
в: Tetrahedron, Том 73, № 19, 11.05.2017, стр. 2717-2726.Результаты исследований: Научные публикации в периодических изданиях › статья › Рецензирование
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TY - JOUR
T1 - Synthesis of a new class of bisheterocycles via the Heck reaction of eudesmane type methylene lactones with 8-bromoxanthines
AU - Patrushev, Sergey S.
AU - Rybalova, Tatyana V.
AU - Ivanov, Igor D.
AU - Vavilin, Valentin A.
AU - Shults, Elvira E.
PY - 2017/5/11
Y1 - 2017/5/11
N2 - The eudesmane-type methylene lactones (isoalantolactone, alantolactone, 4,15-epoxyisoalantolactone, 2′,2′-dichloro-4H-spiro[cyclopropane-1′,4-eudesma-11(13)-en-8β,12-olide], and alantolactone) react with 8-bromoxanthines (8-bromocaffeine, 8-bromotheobromine, 8-bromo-3-butyltheobromine, 8-bromotheophylline, 8-bromo-9-butyltheophylline) under Heck reaction conditions to produce the target (E)-13-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)eudesma-4(15),11(13)-dien-8β,12-olides and the subsequent endocyclic isomers - 11-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)-13-normethyleudecma-4(15)-7(11)-dien-8α,12-olides. It was revealed that the yield and product ratio depends on the reaction conditions and the structure of methylene lactone. The effectiveness of Pd(OAc)2–caffeine catalytic system has been demonstrated in this reaction. The electric eel acetylcholinesterase inhibitory activity of the eudecmanolide-xanthine hybrids was evaluated. Among the new type bisheterocycles compound 27 with butyl and 2-oxodecahydronaphtho[2,3-b]furan-3(2H)-ylidene)methyl substituents at C-7 and C-8 of the xanthine core showed moderate activity with IC50 value of 40 μM.
AB - The eudesmane-type methylene lactones (isoalantolactone, alantolactone, 4,15-epoxyisoalantolactone, 2′,2′-dichloro-4H-spiro[cyclopropane-1′,4-eudesma-11(13)-en-8β,12-olide], and alantolactone) react with 8-bromoxanthines (8-bromocaffeine, 8-bromotheobromine, 8-bromo-3-butyltheobromine, 8-bromotheophylline, 8-bromo-9-butyltheophylline) under Heck reaction conditions to produce the target (E)-13-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)eudesma-4(15),11(13)-dien-8β,12-olides and the subsequent endocyclic isomers - 11-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)-13-normethyleudecma-4(15)-7(11)-dien-8α,12-olides. It was revealed that the yield and product ratio depends on the reaction conditions and the structure of methylene lactone. The effectiveness of Pd(OAc)2–caffeine catalytic system has been demonstrated in this reaction. The electric eel acetylcholinesterase inhibitory activity of the eudecmanolide-xanthine hybrids was evaluated. Among the new type bisheterocycles compound 27 with butyl and 2-oxodecahydronaphtho[2,3-b]furan-3(2H)-ylidene)methyl substituents at C-7 and C-8 of the xanthine core showed moderate activity with IC50 value of 40 μM.
KW - Acetylcholinesterase inhibitors
KW - Heck reaction
KW - Isoalantolactone
KW - Sesquiterpene lactones
KW - Xanthine
KW - PURINES
KW - XANTHINE DERIVATIVES
KW - ISOALANTOLACTONE
KW - ALANTOLACTONE
KW - SESQUITERPENE LACTONES
KW - INHIBITION
KW - ACETYLCHOLINESTERASE
KW - MONOAMINE-OXIDASE-B
KW - TRANSFORMATIONS
KW - WATER
UR - http://www.scopus.com/inward/record.url?scp=85016418486&partnerID=8YFLogxK
U2 - 10.1016/j.tet.2017.03.016
DO - 10.1016/j.tet.2017.03.016
M3 - Article
AN - SCOPUS:85016418486
VL - 73
SP - 2717
EP - 2726
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 19
ER -
ID: 10267465