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Meneghetti F, Masciocchi D, Gelain A, et al. Crystal structure of 3-(3-oxo-2,3,4,4a,5,6-hexa-hydro-benzo[h]cinnolin-2-yl)propionic acid. Acta Crystallogr Sect E Struct Rep Online. 2014;70:o1088-9doi: 10.1107/S1600536814019850.
Meneghetti, F., Masciocchi, D., Gelain, A., & Villa, S. (2014). Crystal structure of 3-(3-oxo-2,3,4,4a,5,6-hexa-hydro-benzo[h]cinnolin-2-yl)propionic acid. Acta crystallographica. Section E, Structure reports online, 70o1088-9. https://doi.org/10.1107/S1600536814019850
Meneghetti, Fiorella, et al. "Crystal structure of 3-(3-oxo-2,3,4,4a,5,6-hexa-hydro-benzo[h]cinnolin-2-yl)propionic acid." Acta crystallographica. Section E, Structure reports online vol. 70 (2014): o1088-9. doi: https://doi.org/10.1107/S1600536814019850
Meneghetti F, Masciocchi D, Gelain A, Villa S. Crystal structure of 3-(3-oxo-2,3,4,4a,5,6-hexa-hydro-benzo[h]cinnolin-2-yl)propionic acid. Acta Crystallogr Sect E Struct Rep Online. 2014 Sep 06;70:o1088-9. doi: 10.1107/S1600536814019850. eCollection 2014 Oct 01. PMID: 25484687; PMCID: PMC4257230.
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Acta Crystallogr Sect E Struct Rep Online. 2014 Sep 06;70:o1088-9. doi: 10.1107/S1600536814019850. eCollection 2014 Oct 01.

Crystal structure of 3-(3-oxo-2,3,4,4a,5,6-hexa-hydro-benzo[h]cinnolin-2-yl)propionic acid.

Acta crystallographica. Section E, Structure reports online

Fiorella Meneghetti, Daniela Masciocchi, Arianna Gelain, Stefania Villa

Affiliations

  1. Department of Pharmaceutical Sciences, University of Milano, via L. Mangiagalli, 25, 20133-Milano, Italy.

PMID: 25484687 PMCID: PMC4257230 DOI: 10.1107/S1600536814019850

Abstract

The asymmetric unit of the title compound, C15H16N2O3, contains two independent mol-ecules, which present a different conformation of the carb-oxy-lic acid side chain [C-C-C-OH torsion angles = 65.3 (7) and -170.1 (5)°]. In both mol-ecules, the di-hydro-pyridazinone ring adopts a geometry inter-mediate between a twisted-boat and a half-chair conformation, while the central six-membered ring is almost in a half-boat conformation. In the crystal, mol-ecules are linked by O-H⋯Ok (k = ketone) hydrogen bonds, generating [01-1] chains. Aromatic π-π stacking contacts between the benzene and the di-hydro-pyridazinone rings [centroid-centroid distance [3.879 (9) Å] are also observed.

Keywords: crystal structure; pyridazinone moiety; stat3 inhibitor

References

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  2. J Med Chem. 1990 Jun;33(6):1591-4 - PubMed
  3. J Med Chem. 1996 Oct 25;39(22):4396-405 - PubMed

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