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Microwave-Induced Ugi-Four Component Reactions: Synthesis of New Hetero- Steroid-Amino Acid Conjugates NEWS RELEASE: 29-09-2020

The article by Preetismita Borah and colleagues is published in Current Organic Synthesis, Volume 17, Issue 8, 2020

Steroid hybrid molecules have recently attracted great attention from researchers in recent years owing to their bioactive properties. Earlier a team of researchers led by Dr. Bumal Banik and colleagues, reported the synthesis of several steroid-peptide conjugates of a potential biologically important class of steroid hybrid molecules. During the course of this study, the researchers have come to realize the diverse and interesting biological activities of hetero-steroids. The team recently performed microwave-induced synthesis of steroid-peptide conjugates based on some hetero-steroids containing N, O and S coupling with N-(tert-butoxycarbonyl)-L-phenylalanine as the amino acid residue following Ugi-4-component reaction (Ugi-4-CR). Hetero-steroids are first synthesized from available steroids. These are subjected to Ugi-4-CR to obtain a number of hetero-steroid-peptide conjugates - a new class of steroid-peptide conjugate. Their research findings have been published in a in Current Organic Synthesis.

The synthesis of hetero-steroid-amino acid conjugate starting from epiendrosterone to incorporate a heterocyclic ring fused to its D-ring is described in the article. To synthesize the Hetero-steroid-amino acid conjugate starting from easily available progesterone, a different approach is adopted. The Heterosteroid-amino acid conjugate is also prepared starting from 3β-acetoxy-19-formyloxy-7-iodo-6-nor-5,7-seco-pregnan-5,20-dione.

The team believes that this method will undoubtedly find a significant place in organic synthesis processes. "Microwave-promoted Ugi-4CR towards the synthesis of a new class of hybrid molecules, viz., Hetero-steroid-amino acid conjugates based on hetero-steroidal amines is a useful addition to synthetic organic chemistry. "Says Dr Banik. "Additionally, hetero-steroid-amino acid conjugates may have diverse biological properties, which adds to their value.", he concludes. Under classical conditions, synthesis of many of these compounds as described here proves to be problematic due to the occurrence of undesirable side reactions. In contrast, the microwave method is proved to be excellent in terms of the yields of the products and rapidity of the reactions.

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Authors :

Preetismita Boraha*, V. D. Shiblinga, Pritish Chowdhuryb, and Bimal Krishna Banik*C

aAgrionics-Pre harvest technologies, CSIR- Central Scientific Instruments Organization, Chandigarh, 160030, India;; bChemical Science & Technology Division, CSIR-North-East Institute of Science & Technology, Jorhat-785006, Assam, India; cDepartment of Mathematics and Natural Sciences, College of Sciences and Human Studies, Prince Mohammad Bin Fahd University, Al Khobar, Kingdom of Saudi Arabia;

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