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Chemical methods for the conversion of Prednisolone to 11-β-hydroxy-1,4-androstadiene-3,17-dione

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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.

A few chemical methods were investigated for the side chain cleavage of prednisolone in order to obtain 11-β-hydroxy-1,4-androstadiene-3,17-dione. Among these methods, ZnCl2 mediated transformation gives the best results with 76% yield.

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Acknowledgements

The authors thank Dr. G. N. Qazi, Hon’ble Vice Chancellor, Jamia Hamdard- New Delhi for providing the facilities. SS thanks Hamdard National Foundation for providing Hamdard Centenary Research Fellowship.

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Authors and Affiliations

  1. Department of Industrial Chemistry, Jawaharlal Nehru Technological University, Anantapur, India

    PINNAMA REDDY SURYA PRATAP & NAYAKANTI DEVANNA

  2. Department of Chemistry, Faculty of Science, Jamia Hamdard, Hamdard Nagar, New Delhi, 110 062, India

    SYED SHAFI

  3. Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Jamia Hamdard, Hamdard Nagar, New Delhi, 110 062, India

    FATIMA NAAZ

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  1. PINNAMA REDDY SURYA PRATAP
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  2. SYED SHAFI
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Correspondence to SYED SHAFI.

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SURYA PRATAP, P.R., SHAFI, S., NAAZ, F. et al. Chemical methods for the conversion of Prednisolone to 11-β-hydroxy-1,4-androstadiene-3,17-dione. J Chem Sci 127, 1827–1830 (2015). https://doi.org/10.1007/s12039-015-0950-7

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