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Journal of Chemical Crystallography

, Volume 42, Issue 8, pp 783–789 | Cite as

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

  • Raza Murad Ghalib
  • Rokiah Hashim
  • Solhe F. Alshahateet
  • Sayed Hasan Mehdi
  • Othman Sulaiman
  • Kit-Lam Chan
  • Vikneswaran Murugaiyah
  • Ali Jawad
Original Paper

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.

Keywords

Synthesis Crystal structure 3a,8a-Dihydroxy-1,3-diphenyl-1,3,3a,8a-tetrahydro-indeno[1,2-d]imidazole-2,8-dione 3a,8a-Dihydroxy-1,3-diphenyl-2-thioxo-2,3,3a,8a-tetrahydro-1H-indeno[1,2-d]imidazol-8-one Antimicrobial activity Cholinesterase enzymes inhibitory activity 

Notes

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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Copyright information

© Springer Science+Business Media, LLC 2012

Authors and Affiliations

  • Raza Murad Ghalib
    • 1
  • Rokiah Hashim
    • 1
  • Solhe F. Alshahateet
    • 2
  • Sayed Hasan Mehdi
    • 1
  • Othman Sulaiman
    • 1
  • Kit-Lam Chan
    • 3
  • Vikneswaran Murugaiyah
    • 4
  • Ali Jawad
    • 5
  1. 1.School of Industrial TechnologyUniversiti Sains MalaysiaPulau-PinangMalaysia
  2. 2.Department of ChemistryMutah UniversityAl KarakJordan
  3. 3.Discipline of Pharmaceutical Chemistry, School of Pharmaceutical SciencesUniversiti Sains MalaysiaPenangMalaysia
  4. 4.Discipline of Pharmacology, School of Pharmaceutical SciencesUniversiti Sains MalaysiaPenangMalaysia
  5. 5.Department of Applied PhysicsZakir Husain College of Engineering and Technology, AMUAligarhIndia

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