A Conformational Study of the Semisynthetic Ergot Alkaloid - Terguride

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Title:A Conformational Study of the Semisynthetic Ergot Alkaloid - Terguride
Creators:
Hušák, Michal
Kratochvíl, Bohumil
Sedmera, Petr
Stuchlík, Josef
Jegorov, Alexandr
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 58, 12, pp. 2944-2954

Abstract

Conformational analysis studied by 2D NMR techniques and X-ray diffraction methods are reported for the semisynthetic ergot alkaloid - terguride, in the form of free base and as the protonated species. The structure of terguride hydrogen maleate monohydrate (C<sub>20</sub>H<sub>29</sub>N<sub>4</sub>O)<sup>+</sup>(C<sub>4</sub>H<sub>3</sub>O<sub>4</sub>)<sup>-</sup> . H<sub>2</sub>O (<i>II</i>) was solved by direct methods and refined anisotropically to an <i>R</i>value of 0.068 for 1 991 unique observed reflections. The title compound crystallizes in the triclinic space group <i>P1</i> with lattice parameters <i>a</i> = 7.061(2), <i>b</i> = 9.205(1), <i>c</i> = 12.223(4) Å, α = 96.36(2), β = 107.15(2), γ = 106.67(1)°. Studies revealed that terguride monohydrate (<i>I</i>) and its protonized form (terguride hydrogen maleate monohydrate) possesses the identical conformations both in solutions and in the solid state - an envelope for C and Chair for D ergoline rings.

Title:A Conformational Study of the Semisynthetic Ergot Alkaloid - Terguride
Creators:
Hušák, Michal
Kratochvíl, Bohumil
Sedmera, Petr
Stuchlík, Josef
Jegorov, Alexandr
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:58
Number:12
Page Range:pp. 2944-2954
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19932944UNSPECIFIED
ID Code:408
Item Type:Article
Deposited On:06 Feb 2009 17:00
Last Modified:06 Feb 2009 16:00

Citation

Hušák, Michal; Kratochvíl, Bohumil; Sedmera, Petr; Stuchlík, Josef; Jegorov, Alexandr (1993) A Conformational Study of the Semisynthetic Ergot Alkaloid - Terguride. Collection of Czechoslovak Chemical Communications, 58 (12). pp. 2944-2954. ISSN 0010-0765

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