A novel transition state analog inhibitor of guanase based on azepinomycin ring structure: Synthesis and biochemical assessment of enzyme inhibition

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 2, 2011, Pages 756-759

  Chakraborty, Saibal ^a   Shah, Niti H ^a   Fishbein, James C ^a   Hosmane, Ramachandra S ^a  

^a UNIVERSITY OF MARYLAND BALTIMORE COUNTY   (United States)

Author keywords

Azepinomycin analog; Biochemical screening; Imidazo 4,5 e 1,4 diazepine 5,8 dione ring system; Inhibition of guanine deaminase (guanase); Synthesis

Indexed keywords

3 BENZYL 4,5,7,8 TETRAHYDRO 6 (BENZYLOXYCARBONYL)AMINO 6 ETHOXYCARBONYLIMIDAZO[4,5-E][1,4]DIAZEPINE 5,8 DIONE; 3 BENZYL 4,5,7,8 TETRAHYDRO 6HYDROXYMETHYL 6 [(BENZYLOXYCARBONYL) AMINO]IMIDAZO[4,5 E][1,4]DIAZEPINE 5,8 DIONE; AZEPINOMYCIN; DIETHYL 2 (BENZYLOXYCARBONYL)AMINO 2 [N (1 BENZYL 5 NITROIMIDAZOLYL 4 CARBONYL)AMINO] MALONATE; DIETHYL 2 (BENZYLOXYCARBONYL)AMINO 2 [N (5 AMINO 1 BENZYLIMIDAZOLYL 4 CARBONYL)AMINO]MALONATE; DIETHYL 2 AMINO 2 [N (1 BENZYL 5 NITROIMIDAZOLYL 4 CARBONYL)AMINO]MALONATE; ENZYME INHIBITOR; GUANINE DEAMINASE; UNCLASSIFIED DRUG; XANTHINE; ZINC ION;

ANIMAL TISSUE; ARTICLE; BIOCHEMISTRY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME INHIBITION; HYDROLYSIS; NONHUMAN; RABBIT;

ANIMALS; AZEPINES; ENZYME INHIBITORS; GUANINE DEAMINASE; LIVER; RABBITS; STRUCTURE-ACTIVITY RELATIONSHIP;

HUMAN ECHOVIRUS 1; ORYCTOLAGUS CUNICULUS;

EID: 78651327314     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.11.109     Document Type: Article

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43. +). 3-Benzyl-4,5,7,8-tetrahydro-6-(benzyloxycarbonyl) amino-6-ethoxycarbonylimidazo[4,5-e][1,4]diazepine-5,8-dione (9): potassium tert-butoxide (24 mg, 0.21 mmol) was taken in a dry flask with nitrogen line and 5 mL of dry DMF was added and stirred vigorously. To the mixture was added 8 (70 mg, 0.13 mmol). The heterogeneous mixture immediately turns orange. The mixture was vigorously stirred for 2 h and was monitored by TLC. Care should be taken as one of the by-products is very close to the starting material in TLC using ethyl acetate as the solvent system. The resulting yellow liquid was concentrated under vacuum and neutralized and extracted with ethyl acetate. It is then purified by column chromatography using chloroform/methanol (10:1) as the solvent system.