Synthesis and evaluation of substrate-mimicking cytosolic phospholipase A2 inhibitors - Reducing the lipophilicity of the arachidonyl chain isostere

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 14, 2004, Pages 3645-3649

  Walters, Iain ^a   Bennion, Colin ^a   Connolly, Stephen ^a   Croshaw, Pamela J ^a   Hardy, Kim ^a   Hartopp, Paul ^a   Jackson, Clive G ^a   King, Sarah J ^a   Lawrence, Louise ^a   Mete, Antonio ^a   Murray, David ^a   Robinson, David H ^a   Stein, Linda ^a   Wells, Edward ^a   Withnall, W John ^a  

^a ASTRAZENECA   (United Kingdom)

Author keywords

Arachidonyl chain mimic; cPLA2 inhibition

Indexed keywords

PHOSPHOLIPASE A2 INHIBITOR;

ARTICLE; CELL LINE; CYTOSOL; DRUG POTENCY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; LIPOPHILICITY;

ARACHIDONIC ACID; CYTOSOL; ENZYME INHIBITORS; HL-60 CELLS; HUMANS; INHIBITORY CONCENTRATION 50; MOLECULAR MIMICRY; PHOSPHOLIPASES A; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 2942527422     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.05.024     Document Type: Article

References (14)

1. Diez E., Louis-Flamberg P., Hall R.H., Mayer R.J. J. Biol. Chem. 267:1992;18342-18348
2. Clark J.D., Lin L.-L., Kriz R.W., Ramesha C.S., Sultzman L.A., Lin A.Y., Milona N., Knopf J.L. Cell. 65:1991;1043-1051
3. Diez E., Chilton F.H., Stroup G., Mayer R.J., Winkler J.D., Fonteh A.N. Biochem. J. 301:1994;721-726
4. Clark J.D., Schievella A.R., Nalefski E.A., Lin L.-L. J. Lipid Mediators Cell Signaling. 12:1995;83-117
5. Dennis E.A. Drug Dev. Res. 10:1987;205-220
6. Moncada S., Higgs E.A. Ann. N. Y. Acad. Sci. 522:1988;454-463
7. Samuelsson B., Dahlen S.-E., Lindgren J.A., Rouzer C.A., Serhan C.N. Science. 237:1987;1171-1176
8. Lehr M. Drugs Future. 25:2000;823-832
9. Connolly S., Robinson D.H. Exp. Opin. Ther. Pat. 5:1995;673-683
10. Lehr M. Exp. Opin. Ther. Pat. 11:2001;1123-1136
11. Connolly S., Bennion C., Botterell S., Croshaw P.J., Hallam C., Hardy K., Hartopp P., Jackson C.G., King S.J., Lawrence L., Mete A., Murray D., Robinson D.H., Smith G.M., Stein L., Walters I., Wells E., Withnall W.J. J. Med. Chem. 45:2002;1348-1362
12. Huang Z., Laliberte F., Tremblay N.M., Weech P.K., Street I.P. Anal. Biochem. 222:1994;110-115
13. Daylight, version 3.64; Daylight Chemical Information Systems, Inc.: Irvine, CA 92715
14. p values for ether ( - 0.28) and ester ( + 0.44) functional groups: March J. 4th ed. Advanced Organic Chemistry. 1992;Wiley. Chapter 9