Advertisement

Journal of Chemical Crystallography

, Volume 48, Issue 3, pp 78–90 | Cite as

Crystal Structure and Molecular Docking Studies of 1-Ethyl-2′-(furan-2-carbonyl)-1′-(furan-2-yl)-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one

  • Venkata Bharat Nishtala
  • Srinivas Basavoju
Original Paper

Abstract

The title compound, 1-ethyl-2′-(furan-2-carbonyl)-1′-(furan-2-yl)-1′,2′,5′,6′,7′,7a′-hexahydrospiro [indoline-3,3′-pyrrolizin]-2-one (1), was synthesized via a one-pot multicomponent 1,3-dipolar cycloaddition reaction and the structure of the compound 1 was determined by IR, 1H NMR, 13C NMR, Mass spectrometry and single crystal X-ray diffraction method. The compound 1 crystallizes in the centrosymmetric monoclinic P21/n space group with unit cellparameters a = 13.9675(10) Å, b = 9.1490(6) Å, c = 16.6482(14) Å, β = 104.529(4)° and a cell volume of 2059.42 Å3. The crystal structure shows the formation of two-dimensional (2D) layered structure. Each 2D layer was formed by individual enantiomers of the compound 1. The target molecule was formed diastereoselectively via 1,3-dipolar cycloaddition reaction, which was evidenced from its crystal structure. In silico docking studies were carried out to evaluate anti-mycobacterial, anti-microbial and anti-cancer activities using corresponding proteins by using AutoDock Tools version 1.5.6 and AutoDock version 4.2.5.1 docking program. The compound 1 showed good activity against the proteins of mycobacterium tuberculosis (1V10 = − 8.49 kcal/mol), bacterial (4MIO = − 8.64 kcal/mol) and moderate activity against cancer protein (4L9K = − 3.63 kcal/mol).

Graphical Abstract

The title compound, 1-ethyl-2′-(furan-2-carbonyl)-1′-(furan-2-yl)-1′,2′,5′,6′,7′,7a′-hexahydrospiro[indoline-3,3′-pyrrolizin]-2-one (1), crystallizes in the centrosymmetric monoclinic P21/n space group. The crystal structure shows the formation of two-dimensional (2D) layered structure. The target molecule was formed diastereoselectively via 1,3-dipolar cycloaddition reaction, which was evidenced from its crystal structure. Docking studies reveal that the compound 1 showed good activity against the proteins of mycobacterium tuberculosis (1V10 = − 8.49 kcal/mol), bacterial (4MIO = − 8.64 kcal/mol) and moderate activity against cancer protein (4L9K = − 3.63 kcal/mol).

Keywords

Multicomponent reaction 1,3-Dipolar cycloaddition N-Ethyl isatin Crystal structure Spirooxindolopyrrolizidines Molecular docking studies 

Notes

Acknowledgements

SB and NVB thank the MHRD, India for the Research Seed Grant (RSG) and fellowship support. The authors are also thankful to the STIC, Cochin for performing the single crystal X-ray analysis. The authors also thank Dr. Aparna Vema, Sree Chaitanya Institute of Pharmaceutical Sciences, Karimnagar and Dr. Ramakrishna Rao Gamidi, University of Limerick, Ireland for helpful discussions in molecular docking and crystallographic studies.

Supplementary material

10870_2018_709_MOESM1_ESM.docx (416 kb)
Supplementary material 1 (DOCX 416 KB)
10870_2018_709_MOESM2_ESM.pdf (137 kb)
Supplementary material 2 (PDF 136 KB)

References

  1. 1.
    Rahmati A, Ahmadi S, Varzaneh MA (2014) Tetrahedron 70:9512–9521CrossRefGoogle Scholar
  2. 2.
    Esmaeili AA, Salehan F, Habibi A, Fakhari AR (2016) Tetrahedron Lett 57:100–102CrossRefGoogle Scholar
  3. 3.
    Pelit E, Turgut Z (2014) Ultrason Sonochem 21:1600–1607CrossRefPubMedPubMedCentralGoogle Scholar
  4. 4.
    Bazgir A, Ahadi S, Ghahremanzadeh R, Khavasi HR, Mirzaei P (2010) Ultrason Sonochem 17:447–452CrossRefPubMedPubMedCentralGoogle Scholar
  5. 5.
    Lakshmi NV, Tamilisai R, Perumal PT (2011) Tetrahedron Lett 52:5301–5307CrossRefGoogle Scholar
  6. 6.
    Thangamani A (2010) Eur J Med Chem 45:6120–6126CrossRefPubMedPubMedCentralGoogle Scholar
  7. 7.
    Jain R, Sharma K, Kumar D (2012) Tetrahedron Lett 53:1993–1997CrossRefGoogle Scholar
  8. 8.
    Wang CS, Zhu RY, Zheng J, Shi F, Tu SJ (2015) J Org Chem 80:512–520CrossRefPubMedPubMedCentralGoogle Scholar
  9. 9.
    Jayashankaran J, Durga R, Manian RS, Raghunathan R (2004) Tetrahedron Lett 45:7303–7305CrossRefGoogle Scholar
  10. 10.
    Ge SQ, Hua YY, Xia M (2009) Ultrason Sonochem 16:232–236CrossRefPubMedPubMedCentralGoogle Scholar
  11. 11.
    Haddad S, Boudriga S, Porzio F, Soldera A, Askri M, Knorr M, Rousselin Y, Kubicki MM, Golz C, Strohmann C (2015) J Org Chem 80:9064–9075CrossRefPubMedPubMedCentralGoogle Scholar
  12. 12.
    Ghandi M, Yari A, Rezaei SJT, Taheri A (2009) Tetrahedron Lett 50:4724–4726CrossRefGoogle Scholar
  13. 13.
    Karthikeyan SV, Bala BD, Raja VP, Perumal S, Yogeeswari P, Sriram DA (2010) Bioorg Med Chem Lett 20:350–353CrossRefPubMedGoogle Scholar
  14. 14.
    Girgis AS (2009) Eur J Med Chem 44:91–100CrossRefPubMedPubMedCentralGoogle Scholar
  15. 15.
    Periyasami G, Raghunathan R, Surendiran G, Mathivanan N (2008) Bioorg Med Chem Lett 18:2342–2345CrossRefPubMedPubMedCentralGoogle Scholar
  16. 16.
    SMART & SAINT (2001) Software reference manuals. Versions 6.28a & 5.625. Bruker Analytical X-ray Systems Inc., MadisonGoogle Scholar
  17. 17.
    Sheldrick GM (1997) SHELXS97 and SHELXL version 2013, program for the solution and refinement of crystal structures. University of Gottingen, GottingenGoogle Scholar
  18. 18.
    Macrae CF, Bruno IJ, Chisholm JA, Edgington PR, McCabe P, Pidcock E, Monge LR, Taylor R, Van de Streek J, Wood PA (2008) J Appl Cryst 41:466–470CrossRefGoogle Scholar
  19. 19.
    Burnett MN, Johnson CK (1996) ORTEPIII, Report ORNL-6895, Oak Ridge National Laboratory, Tennessee, USAGoogle Scholar
  20. 20.
    Farrugia LJ (1997) J Appl Cryst 30:565–566CrossRefGoogle Scholar
  21. 21.
    Barbour LJ (2001) J Supramol Chem 1:189–191CrossRefGoogle Scholar
  22. 22.
  23. 23.
    Morris GM, Goodsell DS, Halliday RS, Huey R, Hart WE, Belew RK, Olson AJ (1998) J Comput Chem 19:1639–1662CrossRefGoogle Scholar
  24. 24.
    Nishtala VB, Nanubolu JB, Basavoju S (2017) Res Chem Intermed 43:1365–1381CrossRefGoogle Scholar
  25. 25.
    Troshin PA, Peregudov AS, Mühlbacher D, Lyubovskaya RN (2005) Eur J Org Chem.  https://doi.org/10.1002/ejoc.200500048 CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  1. 1.Department of ChemistryNational Institute of Technology WarangalWarangalIndia

Personalised recommendations