| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 1344127 | Tetrahedron: Asymmetry | 2012 | 8 Pages |
Ten enantiomerically pure hydroindene-derived compounds obtained by the transformation of (+)-carotol, the main constituent of carrot seed essential oil, were examined for their ability to inhibit the growth of myeloid leukaemia (HL-60) cancer cell lines. All compounds showed significant activity, which was comparable to the most active volatile organic compounds, such as trans–trans-farnesol, citral and nerolidol. Based on the bioactivity and molecular modelling, a 3D QSAR pharmacophore model was generated.
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(3R,3aS,5S,6S,7aR)-3a,6-Dihydroxy-3-isopropyl-7a-methyl-octahydro-indene-5-carboxylic acidC14H24O4[α]D21=+45.3 (c 4.54, acetone)Source of chirality: (+)-carotolAbsolute configuration: (3R,3aS,5S,6S,7aR)
1-((3R,3aS,5S,6R,7aR)-5,6-Epoxy-3a-hydroxy-3-isopropyl-7a-methyl-octahydro-inden-5-yl)-ethanoneC15H24O3[α]D22=+5.1 (c 3.20, CHCl3)Source of chirality: (+)-carotolAbsolute configuration: (3R,3aS,5S,6R,7aR)
(3R,3aS,5S,6R,7aR)-5,6-Epoxy-3a-hydroxy-3-isopropyl-7a-methyl-octahydro-indene-5-carboxylic acidC14H22O4[α]D25=-2.3 (c 0.82, acetone)Source of chirality: (+)-carotolAbsolute configuration: (3R,3aS,5S,6R,7aR)
1-((1aS,5aR,6aR)-3-Isopropyl-5a-methyl-2,4,5,5a,6,6a-hexahydro-1-oxa-cyclopropa[f]inden-1a-yl)-ethanoneC15H22O2[α]D21=-58.2 (c 1.74, CHCl3)Source of chirality: (+)-carotolAbsolute configuration: (1aS,5aR,6aR)
Formic acid (5R,6R,7aR)-5-acetyl-6-hydroxy-3-isopropyl-7a-methyl-2,4,5,6,7,7a-hexahydro-1H-inden-5-yl esterC16H24O4[α]D25=-121.5 (c 1.87, CHCl3)Source of chirality: (+)-carotolAbsolute configuration: (5R,6R,7aR)
Acetic acid (3aR,5S,6S)-6-acetyl-1-isopropyl-3a-methyl-3,3a,4,5,6,7-hexahydro-2H-inden-5-yl esterC17H26O3[α]D26=+19.1 (c 1.05, CHCl3)Source of chirality: (+)-carotolAbsolute configuration: (3aR,5S,6S)
Acetic acid (3R,3aS,5S,6S,7aR)-3a,6-dihydroxy-3-isopropyl-7a-methyl-octahydro-inden-5-yl esterC15H26O4[α]D20=+44.6 (c 2.51, CHCl3)Source of chirality: (+)-carotolAbsolute configuration: (3R,3aS,5S,6S,7aR)
Acetic acid (3R,3aS,5S,7aR)-3a-hydroxy-3-isopropyl-7a-methyl-6-oxo-octahydro-inden-5-yl esterC15H24O4[α]D21=-52.7 (c 2.88, CHCl3)Source of chirality: (+)-carotolAbsolute configuration: (3R,3aS,5S,7aR)
(R)-1-Isopropyl-3a-methyl-2,3,3a,4-tetrahydro-inden-5-oneC13H18O[α]D21=-12.3 (c 1.14, CHCl3)Source of chirality: (+)-carotolAbsolute configuration: (R)
