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Synthesis, Antimicrobial and Cholinesterase Enzymes Inhibitory Activities of Indeno Imidazoles and X-Ray Crystal Structure of 3a,8a-Dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione

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Abstract

Two indeno imidazoles have been synthesized by the reaction of ninhydrin with diphenylurea and diphenylthiourea. The structures have been determined by spectral analysis. The supramolecular behavior of 3a,8a-Dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione (1) was thoroughly analyzed and reported using X-ray single crystal technique and concepts. The presence of oxygen and nitrogen atoms led to very interesting supramolecular motifs interactions such as nitrogen–oxygen, nitrogen–nitrogen, oxygen–oxygen, nitrogen–hydrogen, and oxygen–hydrogen. 3a,8a-dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-8-one 2 showed good antibacterial activity against B. subtilis and P. aeruginosa, while 3a,8a-dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione 1 only showed antibacterial activity against P. aeruginosa. Both of 1 and 2 were inactive against C. albicans. Derivative 2 demonstrated good cholinesterase enzyme activity unlike derivative 1 which has weak inhibitory activity against these enzymes. Furthermore, 2 was found to be a selective butyrylcholinesterase enzyme inhibitor that has potential use for prevention of further neurodegeneration as well for symptomatic treatment of Alzheimer patients.

Graphical Abstract

The non-covalent interactions involved in the crystal structure of 3a,8a-Dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione (1) were investigated and reported in terms of crystal engineering and supramolecular chemistry. Different motifs of N···H and O···H interactions as well as N···O, N···N, and O···O are adopted by the crystal structure and led to a strong crystal packing.

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References

  1. Hasenknopf B, Lehn J-M, Kneisel BO, Baum G, Fenske D (1996) Angew Chem Int Ed 35:1838

    Article  CAS  Google Scholar 

  2. Day AI (2002) Angew Chem Int Ed 41:275

    Article  CAS  Google Scholar 

  3. Bravo JA (1998) Eur J Org Chem 1998:2565

    Article  Google Scholar 

  4. Anderson S, Anderson HL, Bashall A, McPartlin M, Sanders JKM (1995) Angew Chem Int Ed 34:1096

    Article  CAS  Google Scholar 

  5. Freeman WA (1984) Acta Crystallogr B 40:382

    Article  Google Scholar 

  6. Schmitt J-L, Stadler A-M, Kyritsakas N, Lehn J-M (2003) Helv Chim Acta 86:1598

    Article  CAS  Google Scholar 

  7. Lehn JM (1993) Science 260(5115):1762

    Article  CAS  Google Scholar 

  8. Lehn J-M (1995) Supramolecular chemistry. Wiley-VCH. ISBN 978-3527293117

  9. Oshovsky GV, Reinhoudt DN, Verboom W (2007) Angew Chem Int Ed 46(14):2366

    Article  CAS  Google Scholar 

  10. Alshahateet SF, Bishop R, Craig DC, Scudder ML (2011) Cryst Growth Des 11:4474–4483

    Article  CAS  Google Scholar 

  11. Alshahateet SF, Rahman ANMM, Bishop R, Craig DC, Scudder ML (2002) CrystEngComm 4(97):585–590

    Article  CAS  Google Scholar 

  12. MacNicol DD, Downing GR (1996) In: MacNicol D, Toda F, Bishop R (eds) Comprehensive supramolecular chemistry, vol. 6 solid-state supramolecular chemistry: crystal engineering. Pergamon Press, Oxford, Ch 14, pp 421–464

  13. Alshahateet SF, Bishop R, Craig DC, Scudder ML (2001) CrystEngComm 3(48):225–229

    Article  Google Scholar 

  14. Alshahateet SF, Bishop R, Craig DC, Scudder ML (2004) Cryst Growth Des 4:837–844

    Article  CAS  Google Scholar 

  15. Kooli F, Hian PC, Weirong Q, Alshahateet SF, Chen F (2006) J Porous Mater 13:319–324

    Article  CAS  Google Scholar 

  16. Alshahateet SF, Bishop R, Craig DC, Scudder ML (2003) CrystEngComm 3:417–421

    Article  Google Scholar 

  17. Alshahateet SF, Bishop R, Craig DC, Scudder ML (2010) Cryst Growth Des 10:1842–1847

    Article  CAS  Google Scholar 

  18. Alshahateet SF, Bishop R, Scudder ML, Hu CY, Lau EHE, Kooli F, Judeh ZMA, Chow PS, Tan RBH (2005) CrystEngComm 7:139–142

    Article  CAS  Google Scholar 

  19. Alshahateet SF, Bishop R, Craig DC, Scudder ML (2001) CrystEngComm 3(55):264–269

    Article  Google Scholar 

  20. Alshahateet SF, Bishop R, Craig DC, Kooli F, Scudder ML (2008) CrystEngComm 10:297–305

    Article  CAS  Google Scholar 

  21. Alshahateet SF, Ong TT, Bishop R, Kooli F, Messali M (2006) Cryst Growth Des 6(7):1676–1683

    Article  CAS  Google Scholar 

  22. Alshahateet SF, Bishop R, Craig DC, Scudder ML, Ung AT (2001) Struct Chem 12:251–257

    Article  CAS  Google Scholar 

  23. Eloff JN (1998) Planta Med 64:711–713

    Article  CAS  Google Scholar 

  24. Ahmed T, Gilani AH (2009) Pharmacol Biochem Behav 91:554–559

    Article  CAS  Google Scholar 

  25. Siemens Energy and Automation, Inc (1996) SMART and SAINT software reference manuals, Version 4.0. Analytical Instrumentation, Madison, WI

  26. Sheldrick GM (1996) SADABS. University of Göttingen, Göttingen

    Google Scholar 

  27. Sheldrick GM (2008) Acta Crystallogr A64:112–122

    CAS  Google Scholar 

  28. Weinstock M, Groner E (2008) Chem-Biol Interact 175:216–221

    Article  CAS  Google Scholar 

  29. Mesulam M, Guillozet A, Shaw P, Quinn B (2002) Neurobiol Dis 9:88–93

    Article  CAS  Google Scholar 

  30. Desiraju GR, Steiner T (1999) The weak hydrogen bond in structural chemistry and biology. Oxford Science Publications, Oxford

    Google Scholar 

Download references

Acknowledgments

We would like to acknowledge Universiti Sains Malaysia (USM) for the Postdoctoral Fellowship to Dr. Raza Murad Ghalib. We would also like to thank Ms Liew Wai Lam, Ms Claira Arul Aruldass and Mr Mani Maran Marimuthu for their contribution in the present study.

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Authors and Affiliations

  1. School of Industrial Technology, Universiti Sains Malaysia, Minden, 11800, Pulau-Pinang, Malaysia

    Raza Murad Ghalib, Rokiah Hashim, Sayed Hasan Mehdi & Othman Sulaiman

  2. Department of Chemistry, Mutah University, P.O. Box 7, Mutah, Al Karak, 61710, Jordan

    Solhe F. Alshahateet

  3. Discipline of Pharmaceutical Chemistry, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800, Penang, Malaysia

    Kit-Lam Chan

  4. Discipline of Pharmacology, School of Pharmaceutical Sciences, Universiti Sains Malaysia, 11800, Penang, Malaysia

    Vikneswaran Murugaiyah

  5. Department of Applied Physics, Zakir Husain College of Engineering and Technology, AMU, Aligarh, 202002, India

    Ali Jawad

Authors
  1. Raza Murad Ghalib
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  2. Rokiah Hashim
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Correspondence to Raza Murad Ghalib.

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Ghalib, R.M., Hashim, R., Alshahateet, S.F. et al. Synthesis, Antimicrobial and Cholinesterase Enzymes Inhibitory Activities of Indeno Imidazoles and X-Ray Crystal Structure of 3a,8a-Dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione. J Chem Crystallogr 42, 783–789 (2012). https://doi.org/10.1007/s10870-012-0288-7

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