Conformationally constrained analogues of diacylglycerol. 11.1 Ultrapotent protein kinase C ligands based on a chiral 5-disubstituted tetrahydro-2-furanone template

Journal of Medicinal Chemistry

Volumn 39, Issue 1, 1996, Pages 29-35

  Lee, Jeewoo ^a   Wang, Shaomeng ^a   Milne, George W A ^a   Sharma, Rajiv ^a   Lewin, Nancy E ^a   Blumberg, Peter M ^a   Marquez, Victor E ^a  

^a NATIONAL INSTITUTES OF HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,2:3,5 DI O ISOPROPYLIDENE ALPHA D THREO APIOFURANOSE; 5 [(ACETYLOXY)METHYL] 5 (HYDROXYMETHYL) 3 (9 OCTADECAENYLIDENE)TETRAHYDRO 2 FURANONE; 5 [(TETRADECANOYLOXY)METHYL] 5 (HYDROXYMETHYL)TETRAHYDRO 2 FURANONE; 8,9 O ISOPROPYLIDENE 2 OXO 1,7 DIOXASPIRO[4.4]NONANE; DIACYLGLYCEROL; DRUG CARRIER; PROTEIN KINASE C; TETRAHYDRO 2 FURANONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CHIRALITY; DRUG BINDING; DRUG CONFORMATION; DRUG SYNTHESIS; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; STEREOSPECIFICITY;

4-BUTYROLACTONE; BINDING SITES; BINDING, COMPETITIVE; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DIGLYCERIDES; LACTONES; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR CONFORMATION; MOLECULAR STRUCTURE; PHORBOL 12,13-DIBUTYRATE; PROTEIN KINASE C; STEREOISOMERISM;

EID: 0030032407     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm950277n     Document Type: Article

References (14)

1. Sharma, R.; Lee, J.; Lewin, N. E.; Blumberg, P. M.; Marquez, V. E. J. Med. Chem. 1996, 39, 19-28.
2. Rando, R. R.; Young, N. The Stereospecific Activation of Protein Kinase C. Biochem. Biophys. Res. Commun. 1984, 122, 818-823.
3. Boni, L. T.; Rando, R. R. The Nature of Protein Kinase C Activation by Physically Defined Phospholipid Vesicles and Diacylglycerols. J. Biol. Chem. 1985, 260, 10819-10825.
4. Rando, R. R. Regulation of Protein Kinase C Activity by Lipids. FASEB J, 1988, 2, 2348-2355.
5. Wang, S.; Milne, G. W. A.; Nicklaus, M. C.; Marquez, V. E.; Lee, J.; Blumberg, P. M. Protein Kinase C. Modeling of the Binding Site and Prediction of Binding Constants. J. Med. Chem. 1994, 4, 1326-1338.
6. Carey, F. A.; Ball, D. H.; Long, L., Jr. 1,2:3,5-Di-O-Isopropylidene-α-D-Apio-L-Furanose. Carbohydr. Res. 1966, 3, 205-213.
7. Lee, J.; Marquez, V. E.; Lewin, N. E.; Blumberg, P. M. Synthesis of Two Rigid Diacylglycerol Analogues Having a 1,7-Dioxaspiro-[4.4]nonane Bis-γ-Butyrolactone Skeleton. 4. Synlett 1994, 206-208.
8. Cahiez, G.; Alexakis, A.; Normant, J. F. Derives Organomagnesiens ω-Alcoolates: Preparation et Proprietes. Tetrahedron Lett. 1978, 19, 3013-3014.
9. Fukuzawa, S.; Nakanishi, A.; Fujinami, T.; Sakai, S. Reductive Coupling of Ketone or Aldehydes with Electron-deficient Alkenes Promoted by Samarium Di-iodide. J. Chem. Soc., Chem. Commum. 1986, 624-625.
10. Gescher, A.; Dale, I. L. Protein Kinase C. A Novel Target for Rational Anti-Cancer Drug Design? Anti-Cancer Drug Des. 1989, 4, 93-105.
11. Teng, K.; Marquez, V. E.; Milne, G. W. A.; Barchi, J. J., Jr.; Kazanietz, M. G.; Lewin, N. E.; Blumberg, P. M.; Abushanab, E. Conformationally Constrained Analogues of Diacylglycerol. Interaction of γ-Lactones with the Phorbol Ester Receptor of Protein Kinase C. J. Am. Chem. Soc. 1992, 114, 1059-1070.
12. Kazanietz, M. G.; Areres, L. B.; Bahador, A.; Mischak, H.; Goodnight, J.; Mushinski, J. F.; Blumberg, P. M. Characterization of Ligand and Substrate Specificity for the Calcium-Dependent and Calcium-Independent Protein Kinase C Isozymes. Mol. Pharmacol. 1993, 44, 298-307.
13. 6. Acta Crystallogr. 1971, B27, 1718-1730.
14. Allen, F. H.; Bellard, S.; Brice, M. D.; Cartwright, B. A.; Doubleday, A.; Higgs, H.; Hummelink, T.; Hummelink-Peters, B. G.; Kennard, O.; Motherwell, W. D. S.; Rodgers, J. R.; Watson, D. G. The Cambridge Crystal Data Centre: Computer-Based Search, Retrieval, Analysis, and Display of Information. Acta Crystallogr. 1979, B35, 2331-2339.