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Crystal Structure of a Rearranged Cage Compound, 3-Hydroxy-4-aza-8-oxoheptacyclo [9.4.1.02,10.03,14.04,9.09,13.012,15]tetradecane

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Abstract

Polycyclic hydrocarbon compounds exhibit a wide variety of biological activities, ranging from antiviral to Parkinson’s disease. Several structures such as the adamantanes have reached clinical status and are used therapeutically to treat, amongst others, neurodegenerative disorders such as Alzheimer’s. Polycyclics have also been utilised as carrier molecules to facilitate entry of drugs into the brain. The synthesis, molecular and crystal structure of a new polycyclic compound, 3-hydroxy-4-aza-8-oxoheptacyclo[9.4.1.02,10.03,14.04,9.09,13.012,15]tetradecane, are reported. NMR spectroscopy was applied for structure elucidation of the novel compound and a rearrangement mechanism is proposed for its formation. This compound crystallises in the orthorhombic system, space group Pbca (no. 61). The unit cell parameters are: a = 12.3763 (7), b = 11.6597 (6), c = 15.0539 (8) Å, V = 2172.3 (2) Å3 , and Z = 8 molecules in the unit cell. The reported structure was confirmed by X-ray analysis, which showed that the title molecules associate into centrosymmetric dimers via N–H···O hydrogen bonding.

Index Abstract

The synthesis and structure of a new polycyclic compound, 3-hydroxy-4-aza-8-oxoheptacyclo[9.4.1.02,10.03,14.04,9.09,13.012,15]tetradecane, are reported in this article.

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Acknowledgements

Financial assistance from the National Research Foundation (South Africa) is thankfully acknowledged. MRC thanks the University of Cape Town for research support.

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Authors and Affiliations

  1. Pharmaceutical Chemistry, School of Pharmacy, North-West University, Potchefstroom, 2520, South Africa

    Louis H. A. Prins, Armand de Vries, Sandra van Dyk & Sarel F. Malan

  2. Department of Chemistry, University of Cape Town, Rondebosch, Cape Town, 7701, South Africa

    Mino R. Caira

  3. Pharmacology, School of Pharmacy, North-West University, Potchefstroom, 2520, South Africa

    Douglas W. Oliver

Authors
  1. Louis H. A. Prins
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  2. Armand de Vries
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  3. Mino R. Caira
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  4. Douglas W. Oliver
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  5. Sandra van Dyk
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  6. Sarel F. Malan
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Correspondence to Sarel F. Malan.

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Prins, L.H.A., de Vries, A., Caira, M.R. et al. Crystal Structure of a Rearranged Cage Compound, 3-Hydroxy-4-aza-8-oxoheptacyclo [9.4.1.02,10.03,14.04,9.09,13.012,15]tetradecane. J Chem Crystallogr 38, 705–709 (2008). https://doi.org/10.1007/s10870-008-9381-3

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  • DOI: https://doi.org/10.1007/s10870-008-9381-3

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