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Volumn 19, Issue 6, 2009, Pages 1830-1834

Design, synthesis, and structure-activity relationship of novel CCR2 antagonists

Author keywords

Aminocyclopentane carboxamide; CCR2 Antagonist; Chemotaxis; Reductive aminations

Indexed keywords

1 AMINOCYCLOPENTYL 3 CARBOXYAMIDE DERIVATIVE; CHEMOKINE RECEPTOR ANTAGONIST; CHEMOKINE RECEPTOR CCR2; UNCLASSIFIED DRUG;

EID: 61449261080     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2008.12.050     Document Type: Article
Times cited : (23)

References (43)
  • 13
    • 61449256408 scopus 로고    scopus 로고
    • Lapierre, J. M.; Morgans, D.; Wlihelm, R.; Mirzadagaen, T. R. In 26th National Medicinal Chemistry Symposium, Richmond, VA, 1998.
    • Lapierre, J. M.; Morgans, D.; Wlihelm, R.; Mirzadagaen, T. R. In 26th National Medicinal Chemistry Symposium, Richmond, VA, 1998.
  • 29
    • 61449184009 scopus 로고    scopus 로고
    • note
    • Additional evidence regarding the cis-relationship between the amine and ester group in 10 came via the X-ray of 'wrong acid' from the ester 9, where in the amine and carboxyl group had a trans-relationship.
  • 39
    • 61449185875 scopus 로고    scopus 로고
    • note
    • 125I-hMCP-1 was purchased from Perkin Elmer Life Sciences, Inc., with a specific activity of 2200 Ci/mmol. The assay was terminated by filtration of the reaction mixture through GF/B filter plates (presoaked in 0.1% polyethyleneimine) using a Packard Cell Harvester, filter plates were washed with 25 mM Hepes, pH 7.5, containing 500 mM NaCl and dried in an incubator for at 37 °C for 30 min. The plates were loaded with Microscint 0 (Packard) and counted in a Topcount NXT (Packard). The software program Prism (GraphPad) was used for all.
  • 41
    • 61449187794 scopus 로고    scopus 로고
    • note
    • Butora, G. Unpublished experimental observations. Stereochemical relationship was established by comprehensive analysis of the high field NMR studies of the analogs, that were independently synthesized by a route, unlike the one described herein.
  • 42
    • 61449253860 scopus 로고    scopus 로고
    • note
    • We believe that the trans-diastereomer (both the methyl and amine in diaxial disposition) probably was formed during this reaction and but eluded our detection/separation by chiral columns.
  • 43
    • 61449149913 scopus 로고    scopus 로고
    • note
    • +] calculated 396.4; found 397.2 (M+H).Typical reductive amination of (4) with ketones: The reductive amination of (4) with ketones are similar to the Ref. 22.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.