Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin

Ramakrishnamraju Samunuri; Masaaki Toyama; Renuka Sivasankar Pallaka; Seshubabu Neeladri; Ashok Kumar Jha; Masanori Baba; Chandralata Bal

doi:10.1039/d0md00059k

Synthesis and anti-HBV activity of carbocyclic nucleoside hybrids with salient features of entecavir and aristeromycin

RSC Med Chem. 2020 May 15;11(5):597-601. doi: 10.1039/d0md00059k. eCollection 2020 May 1.

Authors

Ramakrishnamraju Samunuri^{1

2}, Masaaki Toyama³, Renuka Sivasankar Pallaka², Seshubabu Neeladri², Ashok Kumar Jha², Masanori Baba³, Chandralata Bal¹

Affiliations

¹ Department of Chemistry , Birla Institute of Technology , Mesra , Ranchi , Jharkhand 835215 , India . Email: cbal@bitmesra.ac.in.
² Chemistry Services , GVK Biosciences Pvt. Ltd , IDA Nacharam , Hyderabad , India.
³ Division of Antiviral Chemotherapy , Joint Research Center for Human Retrovirus Infection , Kagoshima University , 8-35-1, Sakuragaoka , Kagoshima , 890-8544 , Japan.

Abstract

Modified carbocyclic nucleosides (4a-g) constituting 7-deazapurine, 4'-methyl, exocyclic double bond and 2',3'-hydroxy were synthesized. NOE and X-ray studies of 4c confirmed the α-configuration of 4'-methyl. The anti-HBV assay demonstrated 4e (IC₅₀ = 3.4 μM) without notable cytotoxicity (CC₅₀ = 87.5 μM) as a promising lead for future exploration.