作为S-腺苷同型半胱氨酸水解酶有效抑制剂的氟化环戊烯基腺嘌呤的合成。

Synthesis of fluorinated cyclopentenyladenine as potent inhibitor of S-adenosylhomocysteine hydrolase.

作者信息

Kim Hea Ok, Yoo Su Jeong, Ahn Hee Sung, Choi Won Jun, Moon Hyung Ryong, Lee Kang Man, Chun Moon Woo, Jeong Lak Shin

机构信息

Laboratory of Medicinal Chemistry, College of Pharmacy, Ewha Womans University, Seoul 120-750, South Korea.

出版信息

Bioorg Med Chem Lett. 2004 May 3;14(9):2091-3. doi: 10.1016/j.bmcl.2004.02.039.

DOI:10.1016/j.bmcl.2004.02.039

Abstract

Fluoro-DHCeA (4) was efficiently synthesized from d-cyclopentenone derivative 5 using electrophilic fluorination as a key step. Fluoro-DHCeA (4) was found to be as potent as DHCeA (3), but exhibited irreversible inhibition of enzyme unlike DHCeA (3) showing reversible inhibition. From this study, 4(')-hydroxymethyl groups of neplanocin A and fluoro-neplanocin A played an important role in binding to the active site of the enzyme.

摘要

氟代-DHCeA（4）以亲电氟化作为关键步骤，由d-环戊烯酮衍生物5高效合成。发现氟代-DHCeA（4）与DHCeA（3）具有同等效力，但与表现出可逆抑制作用的DHCeA（3）不同，它对酶表现出不可逆抑制作用。从这项研究可知，新制癌菌素A和氟代新制癌菌素A的4(')-羟甲基基团在与酶的活性位点结合中起重要作用。

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