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Cover Picture: Synthesis of Acyclic Selenonucleoside Phosphonates as Potential Antiviral Agents (Asian J. Org. Chem. 2/2016)
Author(s) -
Sahu Pramod K.,
Kim Gyudong,
Nayak Akshata,
Ahn Ji Yoon,
Ha Min Woo,
Park Cheonhyoung,
Yu Jinha,
Park Hyeunggeun,
Jeong Lak Shin
Publication year - 2016
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Reports
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500513
Subject(s) - chemistry , isostere , enantiomer , diselenide , human immunodeficiency virus (hiv) , selenium , sn2 reaction , bromide , adefovir , combinatorial chemistry , organic chemistry , stereochemistry , hepatitis b virus , virology , virus , lamivudine , biology
A class of acyclic selenonucleoside phosphonates were developed based on the bioisosteric concept. Inspired by the potent antiviral activity of adefovir and tenofovir against human immunodeficiency virus (HIV) and hepatitis B virus (HBV), seleno‐adefovir and seleno‐tenofovir were designed because selenium is a chemical isostere of oxygen or sulfur and is more lipophilic. These acyclic selenonucleoside phosphonates were synthesized via the condensation of bromoalkyladenine with a diselenide in the presence of reducing agent. The S N 2 condensation of the secondary bromide during the synthesis of chiral seleno‐tenofovir proceeded with complete conservation of enantiomeric excess. More information can be found in the communication by L. S. Jeong and co‐workers on page 183 in Issue 2, 2016 (DOI: 10.1002/ajoc.201500421).