作为腺苷A3受体配体的Cl-IB-MECA的3'-氟类似物的合成。
Synthesis of 3'-fluoro analogue of Cl-IB-MECA as adenosine A3 receptor ligand.
作者信息
Chun Moon Woo, Lim Moo Hong, Moon Hyung Ryong, Kim Hea Ok, Jacobson Kenneth A, Jeong Lak Shin
机构信息
College of Pharmacy, Seoul National University, Seoul 151-742, Korea.
出版信息
Nucleic Acids Res Suppl. 2003(3):19-20. doi: 10.1093/nass/3.1.19.
3'-Fluoro analogue 1 of selective and potent adenosine A3 receptor agonist, Cl-IB-MECA was synthesized from D-xylose via highly regioselective opening of lyxo-epoxide 4 with fluoride anion. Compared to the high binding affinity of Cl-IB-MECA to the A3 adenosine receptor, the corresponding 3'-fluoro derivative showed remarkably decreased binding affinity, indicating that 3'-hydroxyl group acts as hydrogen bonding donor, not hydrogen bonding acceptor like fluorine atom in binding to the A3 adenosine receptor.
选择性强效腺苷A3受体激动剂Cl-IB-MECA的3'-氟类似物1是由D-木糖通过氟离子对吡喃糖环氧化物4进行高度区域选择性开环反应合成的。与Cl-IB-MECA对A3腺苷受体的高结合亲和力相比，相应的3'-氟衍生物的结合亲和力显著降低，这表明3'-羟基在与A3腺苷受体结合时作为氢键供体，而不像氟原子那样作为氢键受体。
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