Synthesis of Steroidal Indoxyl, and Derivatives from 3-ketosteroid
Abstract
5&alpha-Androstan-17&beta-ol-3-one condenses with 2-nitrobenzaldehyde in alkaline conditions to give the steroidal indoxyl 17&beta-hydroxy-1-(3′-oxoindan-2′-yliden)-3-nor-1,2-secoandrostan-3-oic acid (I) which on refluxing with acetic anhydride affords the lactam 17&beta-acetoxy-3′-aza-4a-homoandrost-1-eno-(3,2-a)-indan-3′,4-dione (II). Reduction of I with sodium borohydride gives the indole 17&beta-hydroxy-1-(indol-2′-yl)-3-nor-1, 2-secoandrostan-3-oic acid (III). The results of this synthesis suggest that 3-ketosteroids saturated in ring A react in a similar manner to 17-ketosteroids, with 2-nitrobenzaldehyde.
URI
http://www.ajol.info/index.php/ecajps/article/view/9725http://erepository.uonbi.ac.ke:8080/xmlui/handle/123456789/52923
Citation
The East and Central African Journal of Pharmaceutical Sciences Vol. 8 (3) 2005: pp. 43-44Publisher
University of Nairobi Department of Pharmaceutical Chemistry, School of Pharmacy, College of Health Sciences, University of Nairobi.
Collections
- Faculty of Health Sciences (FHS) [10387]