Synthesis of Ara-Neplanocin A Analogues at Sub-Ambient Temperatures Using Microwave Irradiation

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Neplanocin A (NPA, 1), a cyclopentenyl analog of adenosine, is a natural occurring antiviral agent and antibiotic which exhibits anti-tumor activity both in vitro and in vivo.1 However, neplanocin A is toxic to healthy cells – a major drawback if it were to be used for medicinal reasons. Neplanocin A derivatives would be of great interest if they possessed the therapeutic properties without the cytotoxicity, but little research has been done on this group of analogs. Ara-neplanocin A (ara-NPA, 2) was found to be less toxic while retaining antiviral activity and ara-neplanocin C (ara-NPC, 3) has shown anti-tumor activity. Due to the potential of these analogs as useful antimicrobial drugs and in the treatment of cancers, Professor Chung Chu at the University of Georgia, College of Pharmacy developed a convergent synthetic strategy to obtain a host of base modified ara-neplanocins whose biological activities have yet to be explored.2

Figure 1. NPA and known analogs ara-NPA and ara-NPC