2-Piperazinecarboxamides as potent and selective melanocortin subtype-4 receptor agonists

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 8, 2005, Pages 1993-1996

  Palucki, Brenda L ^a   Park, Min K ^a   Nargund, Ravi P ^a   Tang, Rui ^a   MacNeil, Tanya ^a   Weinberg, David H ^a   Vongs, Aurawan ^a   Rosenblum, Charles I ^a   Doss, George A ^a   Miller, Randall R ^a   Stearns, Ralph A ^a   Peng, Qianping ^a   Tamvakopoulos, Constantin ^a   Van Der Ploeg, Lex H T ^a   Patchett, Arthur A ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Melanocortin; Piperazinecarboxamide

Indexed keywords

AMIDE; HORMONE RECEPTOR STIMULATING AGENT; MB 243; MELANOCORTIN 4 RECEPTOR; PIPERAZINE DERIVATIVE;

ALKYLATION; ANIMAL CELL; ARTICLE; CONTROLLED STUDY; COVALENT BOND; DRUG ACTIVITY; DRUG POTENCY; DRUG SCREENING; DRUG SYNTHESIS; FEMALE; MICROSOME; NONHUMAN; SUBSTITUTION REACTION;

EID: 20144389154     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.02.068     Document Type: Article

References (20)

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13. The α-bromoketones were either commercially available or prepared via bromination of ketone using bromine in methanol
14. See Ref. 3 for the synthesis of this intermediate
15. NMR studies were carried out to determine the stereochemistry of the piperazine ring, and the major isomer was assigned trans based on the observed coupling constants
16. Absolute stereochemistry was not determined and minor diastereomer could not be isolated
17. For a detailed description of the assay protocols, see: M.A. Bednarek, T. MacNeil, R.N. Kalyani, R. Tang, L.H.T. Van der Ploeg, and D.H. Weinberg J. Med. Chem. 44 2001 3665
18. M.A. Bednarek, M.V. Siva, B. Arison, T. MacNeil, R.N. Kalyani, R.-R.C. Huang, and D.H. Weinberg Peptides 20 1999 401
19. For a detailed description of the assay protocols, see Ref. 4
20. The tritium group is on the p-fluorophenyl ring of each compound