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Synthesis 2025; 57(02): 251-274
DOI: 10.1055/a-2368-8443
DOI: 10.1055/a-2368-8443
review
Special Topic Dedicated to Prof. H. Ila
Chemical Methods for the Construction of Spirocyclic β-Lactams and Their Biological Importance
P.Y. is grateful for financial support from the University Grants Commission (UGC), New Delhi (58/(OBC) CSIR-UGC NET 2016). S.B. gratefully acknowledges financial support from the University Grants Commission-Basic Science Research (UGC-BSR), Start-Up-Grant (F.30-581/2021), Ministry of Education, Govt. of India and the Central University of Himachal Pradesh. A.B. is grateful for financial support from the Department of Science and Technology (DST), New Delhi, Government of India, (Project No. SR/FT/CS-037/2010 and FIST-II/PURSE-II), the University Grants Commission-Career Advancement Scheme (UGC-CAS) and the SAIF (CIL) at Panjab University, Chandigarh.
Abstract
Spirocyclic β-lactams are a family of natural and synthetic chemicals with different biological activities, including antibacterial properties, and interact with critical physiological targets such as T-type calcium channels and acetyl-CoA cholesterol acyltransferase. Their unique chemical structure, combining a spiro ring system with a β-lactam group, offers promising opportunities for the targeted discovery of medications in medicinal chemistry. Spirocyclic β-lactams have the potential to be adaptable frameworks for developing novel therapeutic medicines with particular three-dimensional pharmacophoric characteristics and increased biological efficacy. Numerous methods are employed for the synthesis of spirocyclic β-lactams, such as cyclization, functional group modifications, asymmetric synthesis utilizing chiral catalysts and biomimetic approaches. In this short review, two distinct approaches describing recent syntheses of spirocyclic β-lactams (from 2021 to 2024) are discussed. The first is based on constructing the β-lactam ring, while the other entails transforming monocyclic β-lactams into spirocyclic structures. These methods include detailed reaction processes and descriptions of the biological functions of the target spirocycles. The applications of spirocyclic β-lactams in medicinal chemistry highlight their role in the synthesis of structurally diverse compounds with significant therapeutic potential, demonstrating creative chemical methods for building complex molecular structures.
1 Introduction
2 β-Lactam Ring Synthesis
3 Non-β-Lactam Ring Synthesis
4 Miscellaneous Examples
5 Conclusion and Outlook
Key words
spirocyclic β-lactams - cycloaddition - cyclization - Cu catalysis - ketene formation - NHC-catalyzed annulationPublication History
Received: 30 May 2024
Accepted after revision: 17 July 2024
Accepted Manuscript online:
18 July 2024
Article published online:
27 August 2024
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