Cyclization of the acyl glucuronide metabolite of a neutral endopeptidase inhibitor to an electrophilic glutarimide: Synthesis, reactivity, and mechanistic analysis

Journal of Medicinal Chemistry

Volumn 50, Issue 24, 2007, Pages 6165-6176

  Meng, Xiaoli ^a   Maggs, James L ^a   Pryde, David C ^b   Planken, Simon ^b   Jenkins, Rosalind E ^a   Peakman, Torren M ^b   Beaumont, Kevin ^b   Kohl, Christopher ^b,c   Park, B Kevin ^a   Stachulski, Andrew V ^a  

^a UNIVERSITY OF LIVERPOOL   (United Kingdom)

^b PFIZER GLOBAL RESEARCH AND DEVELOPMENT   (United Kingdom)

^c ACTELION PHARMACEUTICALS LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

2 [[1 [[(5 ETHYL 1,3,4 THIADIAZOL 2 YL)AMINO]CARBONYL]CYCLOPENTYL]METHYL]PENTANOIC ACID; AMINO ACID DERIVATIVE; BENZYL DERIVATIVE; DRUG METABOLITE; GLUCURONIC ACID; GLUCURONIDE; GLUTARIMIDE; GLUTATHIONE; HUMAN SERUM ALBUMIN; IMIDE; LYSINE; PROTEINASE INHIBITOR; THIOESTER; UNCLASSIFIED DRUG;

ACYLATION; AQUEOUS SOLUTION; ARTICLE; CYCLIZATION; DRUG SYNTHESIS; ELIMINATION REACTION; HALF LIFE TIME; MOLECULAR STABILITY; PH; PKA; REACTION ANALYSIS;

ANIMALS; CYCLIZATION; GLUCURONIDES; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; MALE; NEPRILYSIN; PENTANOIC ACIDS; PIPERIDONES; RATS; RATS, WISTAR; SERUM ALBUMIN; STEREOISOMERISM; THIADIAZOLES;

EID: 37849015197     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm0706766     Document Type: Article

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