The discovery and synthesis of JNJ 31020028, a small molecule antagonist of the Neuropeptide y Y 2 receptor

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 18, 2011, Pages 5552-5556

  Swanson, Devin M ^a   Wong, Victoria D ^a   Jablonowski, Jill A ^a   Shah, Chandra ^a   Rudolph, Dale A ^a   Dvorak, Curt A ^a   Seierstad, Mark ^a   Dvorak, Lisa K ^a   Morton, Kirsten ^a   Nepomuceno, Diane ^a   Atack, John R ^a   Bonaventure, Pascal ^a   Lovenberg, Timothy W ^a   Carruthers, Nicholas I ^a  

^a JOHNSON AND JOHNSON PHARMACEUTICAL RESEARCH AND DEVELOPMENT   (United States)

Author keywords

Neuropeptide Y; Neuropeptide Y Y 2 antagonist; Neuropeptide Y Y 2 receptor

Indexed keywords

JNJ 31020028; MANDELIC ACID; MICROSOMAL TRIGLYCERIDE TRANSFER PROTEIN; NEUROPEPTIDE Y RECEPTOR ANTAGONIST; NEUROPEPTIDE Y Y2 RECEPTOR; NEUROPEPTIDE Y2 RECEPTOR; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; DRUG PROTEIN BINDING; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; IC 50; PHARMACOPHORE; RACEMIZATION; STRUCTURE ACTIVITY RELATION;

BENZAMIDES; CHEMISTRY TECHNIQUES, SYNTHETIC; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DISCOVERY; HUMANS; MOLECULAR STRUCTURE; MOLECULAR WEIGHT; PIPERAZINES; RECEPTORS, NEUROPEPTIDE Y; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 80051919308     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.06.136     Document Type: Article

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21. Racemic JNJ 31020028 was separated by chiral HPLC using a Diacel 1A column (chiral technologies) with a mobile phase of 10% propanol:90% hexanes with a flow rate of 1.5 mL/min. Fraction 1, (-)-enantiomer with retention time of 25.9 min. Optical rotation [ α ] D 20 -26.6 (c 1.2 MeOH). Fraction 2, (+)-enantiomer with retention time of 31.4 min. Optical rotation [ α ] D 20 +26.2 (c 1.2 MeOH) found using a Perkin Elmer Model 341 Polarimeter.
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23. % Ee was determined by chiral HPLC comparison of the resolved enantiomers.