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Microwave Energy in Ugi Four-Component Reaction (Ugi-4CR): Expedient Synthesis of Steroid-Peptide Conjugates Based on Aminosteroids - An Important Class of Hybrid Systems

[ Vol. 14 , Issue. 1 ]

Author(s):

Preetismita Borah, Pritish Chowdhury and Ashma Begum   Pages 120 - 126 ( 7 )

Abstract:


Background: Hybrid systems based on steroids currently are drawing considerable attention in the area of drug development. In our recent work, we reported a Microwave (MW) irradiated Ugi-4 component reaction (Ugi-4CR) in synthesizing a number of steroid-amino acid conjugates based on seco-steroid hydroxyacids (A,B & D ring cleavage) in an expedited way giving very high yield of hybrid products. Considering the importance of steroid based hybrid molecules coupled with advantages of MW energy in organic synthesis, we report here a very high yield synthesis of another class of important hybrid system based on aminosteroids through MWirradiated Ugi-4CR in expedient way.

Methods: The systematic investigation on MW energy in Ugi-4CR reaction to synthesize a noval class of hybrid systems based on aminosteroids to make the conjugation process more facile and greener.

Results: Unlike classic peptide-coupling strategies, the conjugation of peptide to an aminosteroid could provide a number of opportunities both in structural and synthetic, leading to the possibility of legating two or more peptide chains to a steroid based template in a single process. The application of MW energy expedited the conjugation process.

Conclusion: The potential advantages of MW irradiated Ugi-4CR in synthesizing steroid-peptide conjugates based on aminosteroids would undoubtedly find a significant place in commercial synthesis of this class of potential bioactive molecules through green approach. Considering the potential and diverse biological properties associated with steroid hybrid molecules, the present synthesis of steroid-peptide conjugates based on aminosteroids might be of interest in the area of drug development.

Keywords:

Aminosteroids, hybrid systems, microwave energy, peptidomimetics, steroid-peptide conjugates, Ugi-4CR.

Affiliation:

Natural Products Chemistry Division;CSIR-North East Institute of Science & Technology, Jorhat 785006, Assam, India.

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