Structure-affinity relationships of 5′-aromatic ethers and 5′-aromatic sulfides as partial A1 adenosine agonists, potential supraventricular anti-arrhythmic agents

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 14, 2004, Pages 3793-3797

  Morrison, Christopher F ^a   Elzein, Elfatih ^a   Jiang, Bob ^a   Ibrahim, Prabha N ^a   Marquart, Timothy ^a   Palle, Venkata ^a   Shenk, Kevin D ^a   Varkhedkar, Vaibhav ^a   Maa, Tenning ^a   Wu, Lin ^a   Wu, Yuzhi ^a   Zeng, Dewan ^a   Fong, Irving ^a   Lustig, David ^a   Leung, Kwan ^a   Zablocki, Jeff A ^a  

^a CV THERAPEUTICS INC   (United States)

Author keywords

Arrhythmias; Partial A1 agonist; PSVT

Indexed keywords

ADENOSINE A1 RECEPTOR; ADENOSINE A1 RECEPTOR AGONIST; ANTIARRHYTHMIC AGENT; ETHER DERIVATIVE; GUANOSINE 5' O (3 THIOTRIPHOSPHATE); SULFIDE;

ANIMAL TISSUE; ARTICLE; ATRIOVENTRICULAR BLOCK; BINDING AFFINITY; GUINEA PIG; HEART ATRIOVENTRICULAR NODE; HEART SUPRAVENTRICULAR ARRHYTHMIA; ISOLATED HEART; NONHUMAN; STRUCTURE ACTIVITY RELATION;

ADENOSINE; ANIMALS; ANTI-ARRHYTHMIA AGENTS; ARRHYTHMIA; ATRIOVENTRICULAR NODE; BINDING SITES; BUNDLE OF HIS; DOSE-RESPONSE RELATIONSHIP, DRUG; ETHERS; GUINEA PIGS; HEART RATE; HYDROCARBONS, AROMATIC; RECEPTOR, ADENOSINE A1; STRUCTURE-ACTIVITY RELATIONSHIP; SULFIDES;

CAVIA PORCELLUS; SUS SCROFA;

EID: 2942596183     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.04.096     Document Type: Article

References (30)

1. Olah M.E., Stiles G.L. Ann. Rev. Pharmacol. Toxicol. 35:1995;581-606
2. Muller C.E., Scior T. Pharm. Acta Helv. 68:1993;77-111
3. Hutchinson A.J., Webb R.L., Oei H.H., Ghai G.R., Zimmerman M.B., Williams M. J. Pharm. Exp. Therap. 251:1989;47-55
4. Belardinelli, L.; West, A.; Crampton, R.; Berne, R. M. In Regulatory Function of Adenosine, Berne, R. M.; Rall, T. W.; Rubio, R.; 1983; pp 378-398
5. Collis M.G. Br. J. Pharmacol. 78:1983;207-212
6. Edvinsson L., Fredholm B.B. Br. J. Pharmacol. 80:1983;631-637
7. Evans D., Dcherden J., Bristol J.A. Life Sci. 31:1982;2425-2432
8. Lewis C.D., Hourani S.M., Long C.J., Collis M.G. Gen. Pharmacol. 25:1994;1381-1387
9. Pavan B., IJzerman A.P. Biochem. Pharmacol. 56:1998;1625
10. Shryock J.C., Snowdy S., Baraldi P.G., Cacciari B., Spalluto G., Monopoli A., Ongini E., Baker S.P., Belardinelli L. Circulation. 98:1998;711
11. Gao Z., Li Z., Baker S.P., Lasley R.D., Meyer S., Elzein E., Palle V., Zablocki J.A., Blackburn B., Belardinelli L. J. Pharmacol. Exp. Ther. 298:2001;209-218
12. Glover D.K., Ruiz M., Yang J.Y., Koplan B.A., Allen T.R., Smith W.H., Watson D.D., Barrett R.J., Beller G.A. Circulation. 94:1996;1726
13. Fozard J.R., Ellis K.M., Villela Dantas M.F., Tigani B., Mazzoni L. Eur. J. Pharmacol. 438:2002;183
14. Feoktistov I., Biaggioni I. Pharmacol. Rev. 49:1997;381
15. Liang J.T., Jacobson K.A. Proc. Natl. Acad. Sci. U.S.A. 95:1998;6995
16. Belardinelli, L.; Linden, J.; Berne, R. M. In Progress in Cardiovascular Diseases; 1989; Vol. 32, pp 73-97
17. Van Schaick E.A., Zuideveld K.P., Tukker H.E., Langemeijer M.W., IJzerman A.P., Danhof M. J. Pharm. Exp. Therap. 287:1998;21-30
18. Vahlensieck U., Boknik P., Knapp J., Linck B., Muller F.U., Neumann J., Herzig S., Schluter H., Zidek W., Deng M.C., Scheld H.H., Schmitz W. Br. J. Pharmacol. 119:1996;835-844
19. Snowdy S., Liang H.X., Blackburn B., Lum R., Nelson M., Wang L., Pfister J., Sharma B., Wolff A., Belardinelli L. Br. J. Pharmacol. 126:1999;137-146
20. IJzerman A.P., Van der Wenden E.M., Mathot R.A.A., Danhof M., Borea P.A., Varani K. Naunyn-Schmiedenberg's Arch. Pharmacol. 350:1994;638-645
21. Van der Wenden E.M., Frijtag Drabbe Kunzel J.K., Mathot R.A.A., Danhof M., IJzerman A.P., Soudijn W. J. Med. Chem. 38:1995;4000-4006
22. Dalpiaz A., Scatturin A., Varani K., Pecoraro R., Pavan B., Borea P.A. Life Sci. 67:2000;1517-1524
23. Van der Wenden E.M., Carnielli M., Roelen Harlof C.P.F., Lorenzen A., Frijtag Drabbe Kunzel J.K., IJzerman A.P. J. Med. Chem. 41:1998;102-108
24. Wu L., Belardinelli L., Zablocki J.A., Palle V., Shyrock J. Am. J. Physiol. Heart Circ. Physiol. 280:2001;H334-H343
25. Song Y., Wu L., Shyrock J.C., Belardinelli L. Circulation. 105:2002;118-123
26. Palle V.P., Varkhedkar V., Ibrahim P., Ahmed H., Li Z., Gao Z., Ozeck M., Wu Y., Zeng D., Wu L., Leung K., Chu N., Zablocki J. Bioorg. Med. Chem. Lett. 14:2004;535-539
27. Mitsunobu O. Synthesis. 1981;1-8
28. 3, 280 mg, 0.46 mmol) in anhydrous THF (2 mL) was sequentially added 1a (107 mg, 0.284 mmol) followed by a 1 M solution of diisopropylazodicarboxylate (0.53 mL, 0.53 mmol). After stirring for 30 min, 6-chloro-2-benzoxazolethiol (53 mg, 0.29 mmol) as a solution in anhydrous THF (1 mL) was added dropwise and the reaction contents refluxed for 16 h. Reaction contents were filtered, solvent removed in vacuo and the crude material was purified by preparative TLC (5% methanol/dichloromethane) to yield isopropylidene protected 12 (136 mg, 0.250 mmol). Isopropylidene protected 12 (136 mg, 0.250 mmol) was dissolved in 80% acetic acid/water and heated at 90°C for 16 h. Solvent was removed in vacuo, and the crude material was purified by preparative TLC (5% methanol/dichloromethane) to furnish 12 as a white powder (23 mg, 0.046 mmol)
29. Gao Z., Robeva A.S., Linden J. J. Biochem. 1999;729-736
30. LC/MS-MS data suggested that trace levels of 1 (<1 ng/mL) were detected in plasma. These levels represent equal or less than 1% of that of 28 in plasma at the same time point. Based on LC/MS-MS data (provided in Supporting information ) this plasma level of 1 is a metabolite of 28, not a trace impurity in 28