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Bioorganic and Medicinal Chemistry Letters
Volumn 5, Issue 18, 1995, Pages 2133-2138
Increasing the cellular PKC inhibitory activity of balanol: A study of ester analogs
Author keywords

[No Author keywords available]
Indexed keywords

BALANOL; BALANOL DERIVATIVE; PROTEIN KINASE C; PROTEIN KINASE C INHIBITOR; UNCLASSIFIED DRUG;
EID: 0029130895     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(95)00361-V     Document Type: Article
Times cited : (25)
References (19)
  • 11
    • 84921221528 scopus 로고    scopus 로고
    • Jagdmann, G. E., Jr.; Defauw, J. M.; Lai, Y.-S.; Crane, H. M.; Hall, S. E.; Buben, J. A.; Hu, H.; Gosnell, P. A. unpublished results. (±)-N-CBZ-anti-3-hydroxy-4-(4-benzyloxybenzamido)pyrrolidine was prepared from 3-pyrroline (available according to Meyers procedure: Warmus, J.S.; Dilley, G.J.; Meyers, A.I. J. Org. Chem. 1993, 58, 270). 3-Pyrroline was protected, then epoxidized with mCPBA followed by epoxide ring opening using ammonium hydroxide. Coupling with 4-benzyloxybenzoyl chloride yielded the desired pyrrolidine. (±)-anti-2-(4-Benzyloxybenzamido)-1-hydroxycyclopentane was prepared in a similar fashion from commercially available cyclopentene oxide.
  • 12
    • 84921221527 scopus 로고    scopus 로고
    • 7
  • 13
    • 84921221526 scopus 로고    scopus 로고
    • 7 using carbonyldiimidazole in DMF. This was followed by oxidation using sulfamic acid and sodium chlorite in acetonitrile and water. Lindgren, B. O.; Nilsson, T. Acta Chem. Scand. 1973, 27, 888.
  • 14
    • 84921221525 scopus 로고    scopus 로고
    • 50's were determined using a 4 point curve of 10-fold dilutions.
  • 16
    • 84921221524 scopus 로고    scopus 로고
    • 50′s were determined using a 4-point curve of 10-fold dilutions.
  • 17
    • 84921221523 scopus 로고    scopus 로고
    • Stability studies were run in the following manner: Compounds of interest (10 μL of a 5 μmol/mL solution in methanol) were added to human plasma (0.4 mL) at a concentration of 125 μM and incubated at 37 °C. Stability was measured at times of 0, 10, 30, 60 and 120 minutes. After the appropriate time, samples were quenched by treating with methanol (0.8 mL) then centrifuged, after which an aliquot (25 μL) of the plasma supernatant was injected onto an HPLC for quantification of the parent compound and detection of any peaks resulting from hydrolysis products. Methyl ester 7 showed 6% degradation to the acid 2 after 1h incubation and 20% after 2h. Ethyl ester 25 showed 5% degradation to the acid 2 after 2 h incubation. Methyl ester (±)8 showed 7% degradation to the acid 3 after 1 h and 17% after 2 h. Butyl esters 18 and 19 showed no detectible degradation after 2 h incubation. Degradation products were determined to be [[Truncated]]
  • 19
    • 84921221522 scopus 로고    scopus 로고
    • Compounds of interest were added to cells and incubated at 4 °C for 1 h after which the assay proceeded as described above for the neutrophil assay.

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