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Crystal structure of rac-3-[2,3-bis-(phenyl-sulfan-yl)-3H-indol-3-yl]propanoic acid.

Noland WE, Brown CD, Bisel AM, Schneerer AK, Tritch KJ - Acta Crystallogr E Crystallogr Commun (2015)

Bottom Line: The title compound, C23H19NO2S2, was obtained as an unexpected regioisomer from an attempted synthesis of an inter-mediate for a substituent-effect study on ergot alkaloids.This is the first report of a 1H-indole mono-thio-ating at the 2- and 3-positions to give a 3H-indole.In the crystal, the acid H atom is twisted roughly 180° from the typical carb-oxy conformation and forms centrosymmetric O-H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related mol-ecule.

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Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.

ABSTRACT
The title compound, C23H19NO2S2, was obtained as an unexpected regioisomer from an attempted synthesis of an inter-mediate for a substituent-effect study on ergot alkaloids. This is the first report of a 1H-indole mono-thio-ating at the 2- and 3-positions to give a 3H-indole. In the crystal, the acid H atom is twisted roughly 180° from the typical carb-oxy conformation and forms centrosymmetric O-H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related mol-ecule. Together with a weak C-H⋯O hydrogen bond involving the carbonyl O atom, chains are formed along [100].

No MeSH data available.


The ergot alkaloid skeleton, (2), Uhle’s ketone, (3), the intended product, (4), and the synthesis of the title compound (bottom row).
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fig1: The ergot alkaloid skeleton, (2), Uhle’s ketone, (3), the intended product, (4), and the synthesis of the title compound (bottom row).

Mentions: The ergot alkaloids, a family of natural and synthetic compounds based on a tetra­cyclic skeleton [(2), Fig. 1 ▸], have been long known to exhibit various pharmacological activities (Hofmann, 1978 ▸). Examples include pergolide (Gilbert et al., 2000 ▸), bromo­criptine (Weber et al., 1981 ▸), and cabergoline (Dosa et al., 2013 ▸), which have been used as treatments for Tourette’s syndrome, psoriasis, and Parkinson’s disease, respectively. Uhle’s ketone (3) is a commonly used inter­mediate in the synthesis of some ergot alkaloids (Moldvai et al., 2004 ▸; Uhle, 1951 ▸).


Crystal structure of rac-3-[2,3-bis-(phenyl-sulfan-yl)-3H-indol-3-yl]propanoic acid.

Noland WE, Brown CD, Bisel AM, Schneerer AK, Tritch KJ - Acta Crystallogr E Crystallogr Commun (2015)

The ergot alkaloid skeleton, (2), Uhle’s ketone, (3), the intended product, (4), and the synthesis of the title compound (bottom row).
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4645081&req=5

fig1: The ergot alkaloid skeleton, (2), Uhle’s ketone, (3), the intended product, (4), and the synthesis of the title compound (bottom row).
Mentions: The ergot alkaloids, a family of natural and synthetic compounds based on a tetra­cyclic skeleton [(2), Fig. 1 ▸], have been long known to exhibit various pharmacological activities (Hofmann, 1978 ▸). Examples include pergolide (Gilbert et al., 2000 ▸), bromo­criptine (Weber et al., 1981 ▸), and cabergoline (Dosa et al., 2013 ▸), which have been used as treatments for Tourette’s syndrome, psoriasis, and Parkinson’s disease, respectively. Uhle’s ketone (3) is a commonly used inter­mediate in the synthesis of some ergot alkaloids (Moldvai et al., 2004 ▸; Uhle, 1951 ▸).

Bottom Line: The title compound, C23H19NO2S2, was obtained as an unexpected regioisomer from an attempted synthesis of an inter-mediate for a substituent-effect study on ergot alkaloids.This is the first report of a 1H-indole mono-thio-ating at the 2- and 3-positions to give a 3H-indole.In the crystal, the acid H atom is twisted roughly 180° from the typical carb-oxy conformation and forms centrosymmetric O-H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related mol-ecule.

View Article: PubMed Central - HTML - PubMed

Affiliation: Department of Chemistry, University of Minnesota, Minneapolis, MN 55455-0431, USA.

ABSTRACT
The title compound, C23H19NO2S2, was obtained as an unexpected regioisomer from an attempted synthesis of an inter-mediate for a substituent-effect study on ergot alkaloids. This is the first report of a 1H-indole mono-thio-ating at the 2- and 3-positions to give a 3H-indole. In the crystal, the acid H atom is twisted roughly 180° from the typical carb-oxy conformation and forms centrosymmetric O-H⋯N hydrogen-bonded dimers with the indole N atom of an inversion-related mol-ecule. Together with a weak C-H⋯O hydrogen bond involving the carbonyl O atom, chains are formed along [100].

No MeSH data available.