IMBIV   05474
INSTITUTO MULTIDISCIPLINARIO DE BIOLOGIA VEGETAL
Unidad Ejecutora - UE
artículos
Título:
Synthesis and Anti-HIV Activity of Lupane and Olean-18-ene
Autor/es:
FÁTIMA GUTIÉRREZ NICOLÁS; BÁRABARA GORDILLO ROMÁN; J. C. OBERTI; A. ESTÉVEZ-BRAUN; A. G. RAVELO; PEDRO JOSEPH NATHAN
Revista:
JOURNAL OF NATURAL PRODUCTS
Editorial:
AMER CHEMICAL SOC
Referencias:
Lugar: Washington; Año: 2012 vol. 75 p. 669 - 676
ISSN:
0163-3864
Resumen:
Lupane triterpenoids 2 and 5−12 and oleanene
derivatives 13 and 14 were prepared from lupeol (1), betulin
(3), and germanicol (4). They were tested for anti-HIV
activity, and some structure−activity relationships were
outlined. The 20-(S) absolute configuration of epoxylupenone
(8) was assessed by comparison of the observed and DFTcalculated
vibrational circular dichroism spectra. The CompareVOA
2 and 5−12 and oleanene
derivatives 13 and 14 were prepared from lupeol (1), betulin
(3), and germanicol (4). They were tested for anti-HIV
activity, and some structure−activity relationships were
outlined. The 20-(S) absolute configuration of epoxylupenone
(8) was assessed by comparison of the observed and DFTcalculated
vibrational circular dichroism spectra. The CompareVOA
13 and 14 were prepared from lupeol (1), betulin
(3), and germanicol (4). They were tested for anti-HIV
activity, and some structure−activity relationships were
outlined. The 20-(S) absolute configuration of epoxylupenone
(8) was assessed by comparison of the observed and DFTcalculated
vibrational circular dichroism spectra. The CompareVOA
3), and germanicol (4). They were tested for anti-HIV
activity, and some structure−activity relationships were
outlined. The 20-(S) absolute configuration of epoxylupenone
(8) was assessed by comparison of the observed and DFTcalculated
vibrational circular dichroism spectra. The CompareVOA
−activity relationships were
outlined. The 20-(S) absolute configuration of epoxylupenone
(8) was assessed by comparison of the observed and DFTcalculated
vibrational circular dichroism spectra. The CompareVOA
S) absolute configuration of epoxylupenone
(8) was assessed by comparison of the observed and DFTcalculated
vibrational circular dichroism spectra. The CompareVOA
8) was assessed by comparison of the observed and DFTcalculated
vibrational circular dichroism spectra. The CompareVOAVOA
algorithm was employed to support the C-20
configuration assignment. The 20,29 double bond in lupenone (2) and 3-epilupeol (15) was stereoselectively epoxidized to
produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures
2) and 3-epilupeol (15) was stereoselectively epoxidized to
produce 20-(S)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structuresS)-8 and 20-(S)-16, respectively, an assignment in agreement with their X-ray diffraction structures