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

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 9, 2004, Pages 2091-2093

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

^a Ewha Womans University   (South Korea)

^b Pusan National University   (South Korea)

^c Seoul National University   (South Korea)

Author keywords

Antiviral; Carbocyclic nucleosides; Electrophilic fluorination; S Adenosylhomocysteine hydrolase

Indexed keywords

ADENOSYLHOMOCYSTEINASE; CYCLOPENTENONE DERIVATIVE; NEPLANOCIN A;

ARTICLE; DRUG INHIBITION; DRUG POTENCY; DRUG SYNTHESIS; ENZYME ACTIVE SITE; ENZYME BINDING; ENZYME INHIBITION; FLUORINATION;

ADENINE; ADENOSYLHOMOCYSTEINASE; CYCLOPENTANES; ENZYME INHIBITORS; FLUORINE; MAGNETIC RESONANCE SPECTROSCOPY;

EID: 1842690640     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.02.039     Document Type: Article

References (17)

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16. To a stirred solution of 8 (1.50 g, 2.88 mmol) and N- fluorobenzenesulfonimide (1.09 g, 3.46 mmol) in dry tetrahydrofuran (30 mL) was added slowly n-butyl lithium (1.6 M solution in hexanes, 5.40 mL, 8.64 mmol) at -78°C under nitrogen atmosphere and the reaction mixture was stirred at the same temperature for 1 h. After usual work-up, the residue was purified by silica gel column chromatography (hexanes/ethyl acetate=30:1) to give an inseparable mixture (1.16 g) of 9 and its hydrogen substituted derivative in 7/1 ratio.
17. 2: C, 47.81; H, 4.01; N, 27.88. Found: C, 47.88; H, 4.11; N, 27.54.