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Crystal structures of dual dopamine D2 and serotonin 5-HT1A active arylpiperidinyl-2(1H)-3,4-dihydroquinolinones

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Abstract

8-(1-((5-Cyclopentenylpyridin-3-yl)methyl)piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (1) and 8-(1-(3- cyclopentenylbenzyl)piperidin-4-yl)-3,4-dihydroquinolin-2(1H)-one (2) are synthesized and obtained in the crystalline state for X-ray diffraction studies. In the asymmetric unit of compound 1, there are two independent molecules (A and B) having similar conformations. In the crystals of compounds 1 and 2, individual molecules are linked by pairs of N–H•••O hydrogen bonds forming A–A and B–B inversion dimers with R 22 (8) ring motifs. The dimers are stabilized by N–H•••O hydrogen bonds and are linked via C–H•••O short contact interactions, forming a three-dimensional and two-dimensional networks in 1 and 2 respectively. The network in 2 is further stabilized by a number of C–H•••π interactions. Compounds 1 and 2 have a dual dopamine D2 and serotonin 5-HT1A receptor profile.

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References

  1. M. Rowley, L. J. Bristow, and P. H. Hutson, J. Med. Chem., 44, No. 4, 477–501 (2001).

    Article  CAS  Google Scholar 

  2. D. C. Goff and R. I. Shader, in: Schizophrenia, S. R. Hirsch and D. Weinberger (eds.), 2nd ed., Blackwell Publishing, Oxford (2002).

  3. L. H. Lindstrom, Acta Psychiatr. Scand., 77, No. 5, 524–529 (1988).

    Article  CAS  Google Scholar 

  4. A. Newman-Tancredi, D. Cussac, and R. Depoortere, Curr. Opin. Invest. Drugs, 8, No. 7, 539–554 (2007).

    CAS  Google Scholar 

  5. C. A. Jones and A. C. McCreary, Neuropharmacology, 55, 1056–1065 (2008).

    Article  CAS  Google Scholar 

  6. A. Newman-Tancredi, A. B. Assie, N. Leduc, A. M. Ormiere, N. Danty, and C. Cosi, Int. J. Neuropsychopharmacol., 8, 341–356 (2005).

    Article  CAS  Google Scholar 

  7. M. B. Assie, V. Ravailhe, V. Faucillon, and A. Newman-Tancredi, J. Pharmacol. Exp. Ther., 315, 265–272 (2005).

    Article  CAS  Google Scholar 

  8. L. Slot, L. D. Vries, A. Newman-Tancredi, and D. Cussac, Eur. J. Pharmacol., 534, 63–70 (2006).

    Article  Google Scholar 

  9. L. Slot, M. S. Kleven, and A. Newman-Tancredi, Neuropharmacology, 49, 996–1006 (2005).

    Article  Google Scholar 

  10. M. S. Kleven, C. Barret-Grevoz, L. Slot, and A. Newman-Tancredi, Neuropharmacology, 49, 135–143 (2005).

    Article  CAS  Google Scholar 

  11. R. A. Bantick, J. F. W. Deakin, and P. M. Grasby, J. Psychopharmacol., 15, 37–46 (2001).

    Article  CAS  Google Scholar 

  12. N. Ullah, J. Med. Chem., 10, 484–496 (2014).

    Article  CAS  Google Scholar 

  13. N. Ullah, J. Enzyme Inhib. Med. Chem., 29, No 2, 281–291(2014).

  14. U. Ghani, N. Ullah, S. A. Ali, and H. A. Al-Muallem, Asian J. Chem., 26, 8358–8362 (2014).

    Article  Google Scholar 

  15. N. Ullah and A. A. Al-Shaheri, Z. Naturforsch. B, 67, 253–262 (2012).

    Article  CAS  Google Scholar 

  16. X-Area V1.35 and X-RED32 V1.31 Software, STOE & Cie GmbH, Darmstadt, Germany (2009).

  17. G. M. Sheldrick, Acta Crystallogr., Sect A., 64, 112–122 (2008).

    Article  CAS  Google Scholar 

  18. A. L. Spek, Acta Crystallogr., Sect. D, 65, 148–155 (2009).

    Article  CAS  Google Scholar 

  19. C. F. Macrae, P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor, M. Towler, and J. van de Streek, J. Appl. Crystallogr., 39, 453–457 (2006).

    Article  CAS  Google Scholar 

  20. M. Altaf and H. Stoeckli-Evans, Acta Crystallogr., Sect. C, 66, o441–o445 (2009).

    Article  Google Scholar 

  21. N. Ullah and H. Stoeckli-Evans, Acta Crystallogr., Sect. E, 70, o103/o104 (2014).

    Article  Google Scholar 

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Authors and Affiliations

  1. Chemistry Department, King Fahd University of Petroleum and Minerals, Dhahran, Saudi Arabia

    N. Ullah, M. Altaf, M. Mansha & A. O. Ba-Salem

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  1. N. Ullah
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  2. M. Altaf
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  3. M. Mansha
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  4. A. O. Ba-Salem
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Correspondence to N. Ullah.

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Original Russian Text © 2015 N. Ullah, M. Altaf, M. Mansha, A. O. Ba-Salem.

The text was submitted by the authors in English. Zhurnal Strukturnoi Khimii, Vol. 56, No. 7, pp. 1496-1499, November-December, 2015.

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Ullah, N., Altaf, M., Mansha, M. et al. Crystal structures of dual dopamine D2 and serotonin 5-HT1A active arylpiperidinyl-2(1H)-3,4-dihydroquinolinones. J Struct Chem 56, 1441–1445 (2015). https://doi.org/10.1134/S0022476615070318

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  • DOI: https://doi.org/10.1134/S0022476615070318

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