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      https://www.ias.ac.in/article/fulltext/jcsc/127/10/1827-1830

    • Keywords

       

      Prednisolone; 11-𝛽-hydroxy-1,4-androstadiene-3,17-dione; Chemical methods; ZnCl2; Stable Wittig ylide; Reformatsky reaction

    • Abstract

       

      Several microbial transformations of steroids to 17-keto cortisones through side chain cleavage have been presented in the literature; however, yields and product selectivity in these methods were low. In the present study, some new methods have been identified for the side chain cleavage of prednisolone (1) to form 11-𝛽-hydroxy-1,4-androstadiene-3,17-dione (11-𝛽-hydroxy ADD). Prednisolone upon reaction with zinc chloride in dry THF results in the formation of cleavage product in good yield (76%). 11-𝛽-hydroxy ADD (2) has been formed in moderate yield (60%) under the Reformatsky reaction conditions by reacting with zincate. While performing the Wittig reaction using stable ylides, again results in the formation of compound 2 in good yield (56%). Side chain cleavage of prednisolone was confirmed from the physical and analytical data and similar when compared with the literature reports.

    • Author Affiliations

       

      Pinnama Reddy Surya Pratap1 Syed Shafi2 Fatima Naaz3 Nayakanti Devanna1

      1. Department of Industrial Chemistry, Jawaharlal Nehru Technological University, Anantapur, India
      2. Department of Chemistry, Faculty of Science, Jamia Hamdard, Hamdard Nagar, New Delhi 110 062, India
      3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, Hamdard Nagar, New Delhi 110 062, India
    • Dates

       
  • Journal of Chemical Sciences | News

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