Design of new anti-Alzheimer drugs: ring-expansion synthesis and synchrotron X-ray diffraction study of dimethyl 4-ethyl-11-fluoro-1,4,5,6,7,8-hexa-hydro-azonino[5,6-b ]indole-2,3-di-carboxyl-ate

Acta Crystallographica. Section E, Crystallographic Communications
Flavien A A TozePavel V Dorovatovskii

Abstract

The title compound, C20H23FN2O4, is the product of a ring-expansion reaction from a seven-membered fluorinated hexa-hydro-azepine to a nine-membered azonine. The nine-membered azonine ring of the mol-ecule adopts a chair-boat conformation. The C=C and C-N bond lengths [1.366 (3) and 1.407 (3) Å, respectively] indicate the presence of conjugation within the enamine CH2-C=C-N-CH2 fragment. The substituent planes at the C=C double bond of this fragment are twisted by 16.0 (3)° as a result of steric effects. The amine N(Et) N atom has a trigonal-pyramidal configuration (sum of the bond angles = 346.3°). The inter-planar angle between the two carboxyl-ate substituents is 60.39 (8)°. In the crystal, mol-ecules form zigzag chains along [010] by inter-molecular N-H⋯O hydrogen-bonding inter-actions, which are further packed in stacks toward [100]. The title azonino-indole might be considered as a candidate for the design of new Alzheimer drugs.

References

Jun 13, 2003·Journal of Medicinal Chemistry·Martin E KuehneJean M Bidlack
Aug 30, 2003·Organic & Biomolecular Chemistry·Martin E KuehneSusan L Bane
Dec 22, 2005·Acta Crystallographica. Section D, Biological Crystallography·Philip Evans
Dec 25, 2007·Acta Crystallographica. Section A, Foundations of Crystallography·George M Sheldrick
Apr 5, 2011·Acta Crystallographica. Section D, Biological Crystallography·T Geoff G BattyeAndrew G W Leslie
Dec 30, 2014·Acta Crystallographica. Section A, Foundations and Advances·George M Sheldrick
Jan 9, 2015·Acta Crystallographica. Section C, Structural Chemistry·George M Sheldrick
Mar 21, 2017·Acta Crystallographica. Section E, Crystallographic Communications·Van Tuyen NguyenVictor N Khrustalev

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Methods Mentioned

BETA
X-ray

Software Mentioned

CCP4
MOSFLM
SCALA

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