D-Secoestrone derivatives. VII. 3-Methoxy-17-keto-17-benzyl-16,17-secoestra-1,3,5(10)-trien-16-nitrile and (17S) 3-methoxy-17-hydroxy-17-benzyl-16,17-secoestra-1,3,5(10)-trien-16-nitrile
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Dušan Lazar
The two title compounds 3-methoxy-17-keto-17-benzyl-16,17-secoestra-1,3,5(10)-trien-16-nitrile, C26H29NO2, (I) and (17S)-3-methoxy-17-hydroxy-17-benzyl-16,17-secoestra-1,3,5(10)-trien-16-nitrile, C26H31NO2, (II), have similar conformations in the solid state. The models from molecular mechanics calculations show an improvement in the similarity of the calculated (modeled) structures. However, they also revealed that the global energy minimum structure of (I) is a structure with a rotated 17-benzyl moiety. Thus, the difference in the bio logical activity of the two compounds ((I) a moderate anti-oestrogen, (II) biologically inactive) must be primarily caused by the difference in the orientation of the 17-benzyl moiety in the free molecules. In (II), the molecules are linked by weak O—H…N hydrogen bonds, forming spirals along the b direction.
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Articles in the same Issue
- Re-determination of the crystal structure of χ-Fe5C2 Hägg carbide
- The CaAg2—CaZn2—CaAl2 pseudo ternary system: crystal structures and structural stability
- High-temperature phase transitions and intermediate incommensurate modulation of the tridymite form of AlPO4
- Crystal structure of the Aurivillius phases in the system Bi4Ti3O12—PbTiO3
- D-Secoestrone derivatives. VII. 3-Methoxy-17-keto-17-benzyl-16,17-secoestra-1,3,5(10)-trien-16-nitrile and (17S) 3-methoxy-17-hydroxy-17-benzyl-16,17-secoestra-1,3,5(10)-trien-16-nitrile
- Heterodinuclear Ni(II)—Sn(II) complexes from reduced ONNO type Schiff base compounds
- The synthesis, structure and thermal decomposition of some Cu(II) complexes with NNN type ligands and thiocyanate anion
Articles in the same Issue
- Re-determination of the crystal structure of χ-Fe5C2 Hägg carbide
- The CaAg2—CaZn2—CaAl2 pseudo ternary system: crystal structures and structural stability
- High-temperature phase transitions and intermediate incommensurate modulation of the tridymite form of AlPO4
- Crystal structure of the Aurivillius phases in the system Bi4Ti3O12—PbTiO3
- D-Secoestrone derivatives. VII. 3-Methoxy-17-keto-17-benzyl-16,17-secoestra-1,3,5(10)-trien-16-nitrile and (17S) 3-methoxy-17-hydroxy-17-benzyl-16,17-secoestra-1,3,5(10)-trien-16-nitrile
- Heterodinuclear Ni(II)—Sn(II) complexes from reduced ONNO type Schiff base compounds
- The synthesis, structure and thermal decomposition of some Cu(II) complexes with NNN type ligands and thiocyanate anion
