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Volumn 22, Issue 3, 2012, Pages 1384-1387

Synthesis of 3-phenylsulfonylmethyl cyclohexylaminobenzamide-derived antagonists of CC chemokine receptor 2 (CCR2)

Author keywords

Antagonist; CCR2; Chemokine; GPCR

Indexed keywords

3 PHENYLSULFONYLMETHYL CYCLOHEXYLAMINOBENZAMIDE DERIVATIVE; CHEMOKINE RECEPTOR CCR2; CHEMOKINE RECEPTOR CCR2 ANTAGONIST; UNCLASSIFIED DRUG;

EID: 84856208740     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.057     Document Type: Article
Times cited : (3)

References (22)
  • 13
    • 84856229102 scopus 로고    scopus 로고
    • Carter, P. H., Cherney, R. J., Batt, D. G., Duncia, J. V., Gardner, D. S., Ko, S. S., Srivastava, A. S., Yang, M. G. PCT Int. Appl. WO/PCT 2005021500, 2005
    • Carter, P. H., Cherney, R. J., Batt, D. G., Duncia, J. V., Gardner, D. S., Ko, S. S., Srivastava, A. S., Yang, M. G. PCT Int. Appl. WO/PCT 2005021500, 2005.
  • 14
    • 84856229106 scopus 로고    scopus 로고
    • The absolute stereochemical assignments of 4d and 4e were confirmed by an independent synthesis of 4e from a known enantiomerically pure intermediate. See Ref. 13
    • The absolute stereochemical assignments of 4d and 4e were confirmed by an independent synthesis of 4e from a known enantiomerically pure intermediate. See Ref. 13
  • 16
    • 84856234832 scopus 로고    scopus 로고
    • The stereochemical assignments of 20 and 21 were confirmed by NMR analyses on closely related compounds. Note that compounds derived from 21 were inactive towards CCR2 binding
    • The stereochemical assignments of 20 and 21 were confirmed by NMR analyses on closely related compounds. Note that compounds derived from 21 were inactive towards CCR2 binding.
  • 17
    • 84856235071 scopus 로고    scopus 로고
    • For preparation of the (1,2,4)-trisubstituted analogs, see Ref. 12,13
    • For preparation of the (1,2,4)-trisubstituted analogs, see Ref. 12,13
  • 18
    • 84856234833 scopus 로고    scopus 로고
    • Carter, P. H., Cherney, R. J. PCT Int. Appl. WO2002/050019, 2002
    • Carter, P. H., Cherney, R. J. PCT Int. Appl. WO2002/050019, 2002.
  • 19
    • 84856235069 scopus 로고    scopus 로고
    • For the preparation of compounds 6a-c, see Carter, P. H., Cherney, R. J., Batt, D. G., Brown, G. D., Duncia, J. V., Gardner, D. S., Yang, M. G. PCT Int. Appl. WO2005/020899, 2005
    • For the preparation of compounds 6a-c, see Carter, P. H., Cherney, R. J., Batt, D. G., Brown, G. D., Duncia, J. V., Gardner, D. S., Yang, M. G. PCT Int. Appl. WO2005/020899, 2005.
  • 20
    • 84856234529 scopus 로고    scopus 로고
    • Note
    • Conformational searching of 2b, 4b, 5b, 2c, 4c, and 5c, was carried out using the conformational search module of Macromodel v9.7 (Schrodinger, Inc.) and the OPLSAA-2005 force field in vacuum. Conformations were retained if they differed by 0.5A RMSD and had an energy <5 kcal/mol higher than the global minimum. Pairwise overlays of the resulting conformations of 2b and 4b were generated using ROCS (Openeye, Inc.) ranked by comboscore. The overlays were inspected and the best overlap selected. The conformation of 2b from this overlap was then used as the template molecule for the overlay of 5b. An identical sequence was used to align 2c, 4c, and 5c.
  • 22
    • 84856235070 scopus 로고    scopus 로고
    • Carter, P. H., Duncia, J. V., Mudryk, B. M., Randazzo, M. E., Xiao, Z., Yang, M. G., Zhao, R. PCT Int. Appl. WO 2008/014360, 2008
    • Carter, P. H., Duncia, J. V., Mudryk, B. M., Randazzo, M. E., Xiao, Z., Yang, M. G., Zhao, R. PCT Int. Appl. WO 2008/014360, 2008.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.