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Volumn 39, Issue 26, 1996, Pages 5215-5227

Synthesis and protein kinase C inhibitory activities of acyclic balanol analogs that are highly selective for protein kinase C over protein kinase A

Author keywords

[No Author keywords available]

Indexed keywords

BALANOL; CASEIN KINASE II; CYCLIC AMP DEPENDENT PROTEIN KINASE; ISOENZYME; PROTEIN KINASE (CALCIUM,CALMODULIN); PROTEIN KINASE C; PROTEIN KINASE C INHIBITOR; PROTEIN SERINE THREONINE KINASE; PROTEIN TYROSINE KINASE;

EID: 12644287559     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm960581w     Document Type: Article
Times cited : (44)

References (33)
  • 1
    • 0024412493 scopus 로고
    • The Protein Kinase C Family: Heterogeneity and its Implications
    • (a) Kikkawa, U.; Kishimoto, A.; Nishizuka, Y. The Protein Kinase C Family: Heterogeneity and its Implications. Annu. Rev. Biochem. 1989, 58, 31-44.
    • (1989) Annu. Rev. Biochem. , vol.58 , pp. 31-44
    • Kikkawa, U.1    Kishimoto, A.2    Nishizuka, Y.3
  • 2
    • 0023052241 scopus 로고
    • Studies and Perspectives of Protein Kinase C
    • (b) Nishizuka, Y. Studies and Perspectives of Protein Kinase C. Science 1986, 233, 305-312.
    • (1986) Science , vol.233 , pp. 305-312
    • Nishizuka, Y.1
  • 3
    • 0021227676 scopus 로고
    • The Role of Protein Kinase C in Cell Surface Signal Transduction and Tumor Promotion
    • (c) Nishizuka, Y. The Role of Protein Kinase C in Cell Surface Signal Transduction and Tumor Promotion. Nature 1984, 308, 693-698.
    • (1984) Nature , vol.308 , pp. 693-698
    • Nishizuka, Y.1
  • 8
    • 0027937860 scopus 로고
    • Two Chiral Syntheses of threo-3-Hydroxylysine
    • (b) Hughes, P. F.; Smith, S. H.; Olson, J. T. Two Chiral Syntheses of threo-3-Hydroxylysine. J. Org. Chem. 1994, 59, 5799-5802.
    • (1994) J. Org. Chem. , vol.59 , pp. 5799-5802
    • Hughes, P.F.1    Smith, S.H.2    Olson, J.T.3
  • 9
    • 0029018846 scopus 로고
    • Two Efficient Syntheses of (±)-anti-N-Benzyl-3-Amino-4-Hydroxyhexahydroazepine
    • (c) Hu, H.; Jagdmann, G. E., Jr. Two Efficient Syntheses of (±)-anti-N-Benzyl-3-Amino-4-Hydroxyhexahydroazepine. Tetrahedron Lett. 1995, 36, 3659-3662.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 3659-3662
    • Hu, H.1    Jagdmann Jr., G.E.2
  • 12
    • 84989591900 scopus 로고
    • Total Synthesis of Balanol and Designed Analogues
    • (b) Nicolaou, K. C.; Koide, K.; Bunnage, M. Total Synthesis of Balanol and Designed Analogues. Chem. Eur. J. 1995, 1, 454-466.
    • (1995) Chem. Eur. J. , vol.1 , pp. 454-466
    • Nicolaou, K.C.1    Koide, K.2    Bunnage, M.3
  • 14
    • 0029360744 scopus 로고    scopus 로고
    • Molecular Design and Biological Activity of Potent and Selective Protein Kinase Inhibitors Related to Balanol
    • Koide, K.; Bunnage, M. E.; Paloma, L. G.; Kanter, J. R.; Taylor, S. S.; Brunton, L. L.; Nicolaou, K. C. Molecular Design and Biological Activity of Potent and Selective Protein Kinase Inhibitors Related to Balanol. Chem. Biol. 1996, 2, 601-608.
    • (1996) Chem. Biol. , vol.2 , pp. 601-608
    • Koide, K.1    Bunnage, M.E.2    Paloma, L.G.3    Kanter, J.R.4    Taylor, S.S.5    Brunton, L.L.6    Nicolaou, K.C.7
  • 15
    • 0026285357 scopus 로고
    • Protein Kinase Inhibitors: Probes for the Functions of Protein Phosphorylation
    • Casnellie, J. E. Protein Kinase Inhibitors: Probes for the Functions of Protein Phosphorylation. Adv. Pharmacol. 1991, 22, 167-205.
    • (1991) Adv. Pharmacol. , vol.22 , pp. 167-205
    • Casnellie, J.E.1
  • 16
    • 0028036667 scopus 로고
    • Two Practical Syntheses of Sterically Congested Benzophenones
    • (a) Hollinshead, S. P.; Nichols, J. B.; Wilson, J. W. Two Practical Syntheses of Sterically Congested Benzophenones. J. Org. Chem. 1994, 59, 6703-6709.
    • (1994) J. Org. Chem. , vol.59 , pp. 6703-6709
    • Hollinshead, S.P.1    Nichols, J.B.2    Wilson, J.W.3
  • 18
    • 12644275756 scopus 로고    scopus 로고
    • note
    • (S)-12 and (R)-12 were determined to be at least 95% ee by chiral HPLC using a Chiralcel OA column with 50% hexane/2-propanol as the solvent system. Enantiomers (S)-12 and (R)-12 eluted at 14.85 and 19.02 min, respectively. The enantiomeric purity could have been greater than 95%; however, base-line resolution between the two peaks was not quite achieved. Chiral purity was determined at this point by chiral HPLC because the optical rotations of the final products (S)-12b, (R)-12b, and (S)-12c were small and solvent dependent.
  • 19
    • 12644273120 scopus 로고    scopus 로고
    • note
    • Note that in the preparation of 16b it was possible to couple the benzophenone acid chloride 2b selectively with the primary alcohol of 16 in the presence of the unprotected phenol.
  • 20
    • 0029882406 scopus 로고    scopus 로고
    • A Novel and Chiral Synthesis of Both Enantiomers of trans-3-Amino-4-hydroxyhexahydroazepine, a Key Intermediate for the Synthesis of Balanol
    • (a) Naito, T.; Mayumi, T. M.; Tajiri, K.; Ninomiya, I.; Kiguchi, T. A Novel and Chiral Synthesis of Both Enantiomers of trans-3-Amino-4-hydroxyhexahydroazepine, a Key Intermediate for the Synthesis of Balanol. Chem. Pharm. Bull. 1996, 44, 624-626.
    • (1996) Chem. Pharm. Bull. , vol.44 , pp. 624-626
    • Naito, T.1    Mayumi, T.M.2    Tajiri, K.3    Ninomiya, I.4    Kiguchi, T.5
  • 21
    • 84986656983 scopus 로고
    • Synthesis of (3R,4R)-3-Amino-4-hydroxyhexahydroazepine, the Chiral Constituent of the Antibiotic Ophiocordin
    • (b) Müller, A.; Takyar, D. K.; Witt, S.; König, W. A. Synthesis of (3R,4R)-3-Amino-4-hydroxyhexahydroazepine, the Chiral Constituent of the Antibiotic Ophiocordin. Liebigs Ann. Chem. 1993, 651-655.
    • (1993) Liebigs Ann. Chem. , pp. 651-655
    • Müller, A.1    Takyar, D.K.2    Witt, S.3    König, W.A.4
  • 23
    • 12644293209 scopus 로고    scopus 로고
    • Unpublished results
    • Unpublished results.
  • 24
    • 0030572481 scopus 로고    scopus 로고
    • Potent and Selective PKC Inhibitory 5-Membered Ring Analogs of Balanol with Replacement of the Carboxamide Moiety
    • Jagdmann, G. E., Jr.; Defauw, J. M.; Lampe, J. W.; Darges, K. K. Potent and Selective PKC Inhibitory 5-Membered Ring Analogs of Balanol With Replacement of the Carboxamide Moiety. Bioorg. Med. Chem. Lett. 1996, 6, 1759-1764.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 1759-1764
    • Jagdmann Jr., G.E.1    Defauw, J.M.2    Lampe, J.W.3    Darges, K.K.4
  • 25
    • 0028839711 scopus 로고
    • Synthesis and Biological Evaluation of Conformationally Constrained Bicyclic and Tricyclic Balanol Analogues as Inhibitors of Protein Kinase C
    • (a) Mendoza, J. S.; Jagdmann, G. E., Jr.; Gosnell, P. A. Synthesis and Biological Evaluation of Conformationally Constrained Bicyclic and Tricyclic Balanol Analogues as Inhibitors of Protein Kinase C. Bioorg. Med. Chem. Lett. 1995, 5, 2211-2216.
    • (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2211-2216
    • Mendoza, J.S.1    Jagdmann Jr., G.E.2    Gosnell, P.A.3
  • 26
    • 0029935522 scopus 로고    scopus 로고
    • Synthesis and Protein Kinase C Inhibitory Activities of Indane Analogs of Balanol
    • (b) Hu, H.; Hollinshead, S. P.; Hall, S. E.; Kalter, K.; Ballas, L. M. Synthesis and Protein Kinase C Inhibitory Activities of Indane Analogs of Balanol. Bioorg. Med. Chem. Lett. 1996, 6, 973-978.
    • (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 973-978
    • Hu, H.1    Hollinshead, S.P.2    Hall, S.E.3    Kalter, K.4    Ballas, L.M.5
  • 29
    • 12644261757 scopus 로고    scopus 로고
    • note
    • Since it was necessary to use 100% MeOH to elute 3 off the column, it was contaminated with silica; thus, it was not possible to obtain a satisfactory elemental analysis. Because of this, all subsequent analogs were purified by reverse phase HPLC.
  • 31
    • 0029079704 scopus 로고
    • Virtual Kinetics: Using Statistical Experimental Design for Rapid Analysis of Enzyme Inhibitor Mechanisms
    • Bronson, D. D.; Daniels, D. M.; Dixon, J. T.; Redick, C. C.; Haaland, P. D. Virtual Kinetics: Using Statistical Experimental Design for Rapid Analysis of Enzyme Inhibitor Mechanisms. Biochem. Pharmacol., 1995, 50, 823-831.
    • (1995) Biochem. Pharmacol. , vol.50 , pp. 823-831
    • Bronson, D.D.1    Daniels, D.M.2    Dixon, J.T.3    Redick, C.C.4    Haaland, P.D.5
  • 33
    • 0022974603 scopus 로고
    • Sphingosine Inhibition of Protein Kinase C Activity and of Phorbol Dibutyrate Binding in vitro and in Human Platelets
    • Hannun, Y. A.; Loomis, C. R.; Merrill, A. H.; Bell, R. M. Sphingosine Inhibition of Protein Kinase C Activity and of Phorbol Dibutyrate Binding in vitro and in Human Platelets. J. Biol. Chem. 1986, 261, 12604-12609.
    • (1986) J. Biol. Chem. , vol.261 , pp. 12604-12609
    • Hannun, Y.A.1    Loomis, C.R.2    Merrill, A.H.3    Bell, R.M.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.