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Bioorganic and Medicinal Chemistry Letters

Volumn 23, Issue 17, 2013, Pages 4837-4841

Synthesis of quaternary α-amino acid-based arginase inhibitors via the Ugi reaction

(20) Golebiowski, Adam a Whitehouse, Darren a Beckett, R Paul a Van Zandt, Michael a Ji, Min Koo a Ryder, Todd R a Jagdmann, Erik a Andreoli, Monica a Lee, Yung a Sheeler, Ryan a Conway, Bruce a Olczak, Jacek b Mazur, Marzena b Czestkowski, Wojciech b Piotrowska, Wieslawa b Cousido Siah, Alexandra c Ruiz, Francesc X c Mitschler, Andre c Podjarny, Alberto c Schroeter, Hagen d

a Institutes for Pharmaceutical Discovery (United States)

b TriMen Chemicals Ltd (Poland)

c UNIVERSITÉ DE STRASBOURG (France)

d MARS INC (United States)

Author keywords

ABH; Arginase inhibitor; Boronic acid; Metalloenzyme; Ugi reaction

Indexed keywords

AMINO ACID DERIVATIVE; ARGINASE; CARBON; NITROGEN; PIPERIDINE;

ARTICLE; ATOM; CONTROLLED STUDY; DRUG SYNTHESIS; IN VITRO STUDY; X RAY CRYSTALLOGRAPHY;

ABH; ARGINASE INHIBITOR; BORONIC ACID; METALLOENZYME; UGI REACTION;

AMINO ACIDS; AMINOCAPROATES; ARGINASE; BORON COMPOUNDS; CRYSTALLOGRAPHY, X-RAY; ENZYME INHIBITORS; HUMANS; MODELS, MOLECULAR; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84881371784 PISSN: 0960894X EISSN: 14643405 Source Type: Journal
DOI: 10.1016/j.bmcl.2013.06.092 Document Type: Article

Times cited : (33)

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- Measured log D (m log D) data were collected for representative compounds at Analiza, (Cleveland, OH), using a high-throughput automated method: http://analiza.com/adme/logd.html. Calculated log D (c log D) was estimated using ChemAxon log D/P predictive software. http://www.chemaxon.com/products/ calculator-plugins/property-predictors/ While calculated values differed substantially from measured ones, they could be used to rank order compounds. We found that for all compounds tested in our program dibasic diamino boronic acid analogs (e.g., 2a-2h), calculated numbers were consistently shifted to more polar values by 1.5-2.5 units. For monobasic amino boronic acid analogs (e.g., 2i-2k) calculated numbers were consistently shifted to more polar values by 0.5-1.5 units.

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