Novel synthesis and anti-HIV activity of 4'-branched exomethylene carbocyclic nucleosides using a ring-closing metathesis of triene.
The exomethylene of 6 was successfully constructed from the aldehyde 5 using Eschenmoser's reagents. A triene compound 7 was cyclized successfully using Grubbs' II catalyst to give an exomethylene carbocycle nucleus for the target compound. A Mitsunobu reaction was successfully used to condense the natural bases (adenine, thymine, uracil, and cytosine). The synthesized cytosine analogue 20 showed moderate anti-HIV activity (EC(50) = 10.67 microM).
Li
Hua
H
BK-21 Project Team, College of Pharmacy, Chosun University, Kwangju, Republic of Korea.
Yoo
Jin Cheol
JC
Hong
Joon Hee
JH
D000475:Alkenes / Q000737:chemistry*; D019380:Anti-HIV Agents / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry
D000475:Alkenes; D019380:Anti-HIV Agents; D009705:Nucleosides