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Synthesis, characterization, and hypoglycemic activity of 3-(arylsulfonyl)spiroimidazolidine-2,4-diones

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Abstract

Spiroimidazolidine-2,4-diones were prepared from methylcyclohexanones by the Bucherer–Bergs reaction. Synthesis of the target 3-(arylsulfonyl)spiroimidazolidine-2,4-diones was achieved by reaction of arylsulfonyl chlorides with corresponding spiroimidazolidine-2,4-diones. The synthesis was confirmed by spectroanalytical techniques and the crystal structure of 3-(4-methoxyphenylsulfonyl)-6-methyl-1,3-diazaspiro[4.5]decane-2,4-dione, and the purity was checked by GC–MS analysis. The in-vivo hypoglycemic potential of 6-methyl-, 7-methyl-, and 8-methyl-3-(4-methylphenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione was investigated on male albino rats. The screened compounds were found to have excellent hypoglycemic activity. 6-Methyl-3-(4-methylphenylsulfonyl)-1,3-diazaspiro[4.5]decane-2,4-dione was found highly active, reducing the blood glucose level by 60.79% compared with 41.60% by the standard (glipizide) at a dose level of 100 mg/kg of the mice body weight. The 8-methyl isomer was also more potent than the standard, with 48.56% reduction in blood glucose level.

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Authors and Affiliations

  1. Department of Chemistry, Quaid-i-Azam University, Islamabad, 45320, Pakistan

    Zafar Iqbal & Shahid Hameed

  2. Department of Chemistry, Mirpur University of Science and Technology, Mirpur, Azad Kashmir, Pakistan

    Tashfeen Akhtar

  3. Department of Chemistry, Saint Mary’s University, Halifax, NS, B3H 3C3, Canada

    Arthur D. Hendsbee & Jason D. Masuda

Authors
  1. Zafar Iqbal
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  2. Tashfeen Akhtar
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  3. Arthur D. Hendsbee
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  4. Jason D. Masuda
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  5. Shahid Hameed
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Correspondence to Shahid Hameed.

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Iqbal, Z., Akhtar, T., Hendsbee, A.D. et al. Synthesis, characterization, and hypoglycemic activity of 3-(arylsulfonyl)spiroimidazolidine-2,4-diones. Monatsh Chem 143, 497–504 (2012). https://doi.org/10.1007/s00706-011-0600-9

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  • DOI: https://doi.org/10.1007/s00706-011-0600-9

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