Monastrol analogs: A synthesis of pyrazolopyridine, benzopyranopyrazolopyridine, and oxygen-bridged azolopyrimidine derivatives and their biological screening

Bioorganic and Medicinal Chemistry Letters

Volumn 20, Issue 14, 2010, Pages 4073-4076

  Svetlik, Jan ^a   Veizerová, Lucia ^a   Mayer, Thomas U ^b   Catarinella, Mario ^b  

^a Faculty of Natural Sciences   (Slovakia)

^b UNIVERSITY OF KONSTANZ   (Germany)

Author keywords

Biginelli reaction; Hantzsch reaction; Monastrol analogs; Oxygen bridged nitrogen heterocycles

Indexed keywords

BENZOPYRANOPYRAZOLOPYRIDINE DERIVATIVE; MONASTROL; PYRAZOLOPYRIDINE DERIVATIVE; PYRAZOLOPYRIMIDINE DERIVATIVE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BIGINELLI REACTION; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG ACTIVITY; DRUG INHIBITION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; PROTON NUCLEAR MAGNETIC RESONANCE; STRUCTURE ACTIVITY RELATION;

OXYGEN; PYRIMIDINES; THIONES;

EID: 77953872987     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.05.085     Document Type: Article

References (34)

1. Mayer T.U., Kapoor T.M., Haggarty S.J., King R.W., Schreiber S.L., and Mitchison T. J. Sci. 286 (1999) 971
2. Biginelli P. Gazz. Chim. Ital. 23 (1893) 360
3. Kappe C.O. Acc. Chem. Res. 33 (2000) 879
4. Kappe C.O. Eur. J. Med. Chem. 35 (2000) 1043 and references cited therein
5. Basso A.M., Bratcher N.A., Gallagher K.B., Cowart M.D., Zhao C., Sun M., Esbenshade T.A., Brune M.E., Fox G.B., Schmidt M., Collins C.A., Souers A.J., Iyengar R., Vasudevan A., Kym P.R., Hancock A.A., and Rueter L.E. Eur. J. Pharmacol. 540 (2006) 115
6. Wisen S., Androsavich J., Evans C.G., Chang L., and Gestwicki J.E. Bioorg. Med. Chem. Lett. 18 (2008) 60
7. Deres K., Schröder C.H., Paessens A., Goldmann S., Hacker H.J., Weber O., Krämer T., Niewöhner U., Pleiss U., Stoltefuss J., Graef E., Koletzki D., Masantschek R.N.A., Reimann A., Jaeger R., Groß R., Beckermann B., Schlemmer K.-H., Haebich D., and Rübsamen-Wagmann H. Science 299 (2003) 893
8. Blackburn C., Guan B., Brown J., Cullis C., Condon S.M., Jenkins T.J., Peluso S., Ye Y., Gimeno R.E., Punreddy S., Sun Y., Wu H., Hubbard B., Kaushik V., Tummino P., Sanchetti P., Sun D.Y., Daniels T., Tozzo E., Balani S.K., and Raman P. Bioorg. Med. Chem. Lett. 16 (2006) 3504
9. Wyatt E.E., Galloway W.R.J.D., Thomas G.L., Welch M., Loiseleur O., Plowright A.T., and Spring D.R. Chem. Commun. (2008) 4962
10. Cox C.D., Breslin M.J., Whitman D.B., Coleman P.J., Garbaccio R.M., Fraley M.E., Zrada M.M., Buser C.A., Walsh E.S., Hamilton K., Lobell R.B., Tao W., Abrams M.T., South V.J., Huber H.E., Kohl N.E., and Hartman G.D. Bioorg. Med. Chem. Lett. 17 (2007) 2697
11. DeBonis S., Skoufias D.A., Indorato R.-L., Liger F., Marquet B., Laggner C., Benoît J., and Kozielski F. J. Med. Chem. 51 (2008) 1115
12. Tarby C.M., Kaltenbach R.F., Huynh T., Pudzianowski A., Shen H., Ortega-Nanos M., Sheriff S., Newitt J.A., McDonell P.A., Burford N., Fairchild C.R., Vaccaro W., Chen Z., Borzilleri R.M., Naglich J., Lombardo L.J., Gottardis M., Trainor G.L., and Roussell D.L. Bioorg. Med. Chem. Lett. 16 (2006) 2095
13. Sunder-Plassmann N., Sarli V., Gartner M., Utz M., Seiler J., Huemmer S., Mayer T.U., Surrey T., and Giannis A. Bioorg. Med. Chem. 13 (2005) 6094
14. Kim K.S., Lu S., Cornelius L.A., Lombardo L.J., Borzilleri R.M., Schroeder G.M., Sheng C., Rovnyak G., Crews D., Schmidt R.J., Williams D.K., Bhide R.S., Traeger S.C., McDonnell P.A., Mueller L., Sheriff S., Newitt J.A., Pudzianowski A.T., Yang Z., Wild R., Lee F.Y., Batorsky R., Ryder J.S., Ortega-Nanos M., Shen H., Gottardis M., and Roussell D.L. Bioorg. Med. Chem. Lett. 16 (2006) 3937
15. Sakowicz R., Finer J.T., Beraud C., Crompton A., Lewis E., Fritsch A., Lee Y., Mak J., Moody R., Turincio R., Chabala J.C., Gonzales P., Roth S., Weitman S., and Wood K.V. Cancer Res. 64 (2004) 3276
16. Matsuno K., Sawada J., Sugimoto M., Ogo N., and Asai A. Bioorg. Med. Chem. Lett. 19 (2009) 1058
17. Gartner M., Sunder-Plassmann N., Seiler J., Utz M., Vernos I., Surrey T., and Giannis A. ChemBioChem 6 (2005) 1173
18. Sarli V., Huemmer S., Sunder-Plassmann N., Mayer T.U., and Giannis A. ChemBioChem 6 (2005) 2005
19. Klein E., DeBonis S., Thiede B., Skoufias D.A., Kozielski F., and Lebeau L. Bioorg. Med. Chem. 15 (2007) 6474
20. Svetlik J., Veizerova L., and Kettmann V. Tetrahedron Lett. 49 (2008) 3520
21. Mayer, T. U. Unpublished results.
22. Quiroga J., Insuasty B., Hormaza A., Saitz C., and Jullian C. J. Heterocycl. Chem. 35 (1998) 575
23. Quiroga J., Mejia D., Insuasty B., Abonia R., Nogueras M., Sanchez A., Cobo J., and Low J.N. Tetrahedron 57 (2001) 6947
24. Quiroga J., Insuasty B., Rincon R., Larrahondo M., Hanold N., and Meier H. J. Heterocycl. Chem. 31 (1994) 1333
25. Svetlik J., Turecek F., and Hanus V. J. Chem. Soc., Perkin Trans. 1 (1988) 2053
26. Svetlik J., Hanus V., and Bella J. Liebigs Ann. Chem. (1989) 91
27. Svetlik J., Turecek F., and Hanus V. J. Chem. Soc., Perkin Trans. 1 (1990) 1315
28. Papadopoulos E.P., and Hollstein U. Org. Magn. Reson. 19 (1982) 188
29. Lopyrev V.A., Larina L.I., Vakulskaya T.I., Shibanova E.F., Titova I.A., Voronkov M.G., and Liepinsh E.E. Org. Magn. Reson. 20 (1982) 212
30. Claramunt R.M., Elguero J., and Meco T. J. Heterocycl. Chem. 20 (1983) 1245
31. Bartashevich E.V., Plekhanov P.V., Rusinov G.L., Potemkin V.A., Belik A.V., and Chupakhin O.N. Izv. Akad. Nauk SSSR Ser. Khim. (1999) 1573
32. Svetlik J., Hanus V., and Bella J. J. Chem. Res., Synop. (1991) 4
33. Kettmann V., Svetlik J., and Veizerova L. Acta Crystallogr., Sect. E 65 (2009) 2967
34. 2-1), 82.9 (C-5), 116.4 (CH-7), 119.3 (CH-9), 120.6 (C-10a), 129.4 (CH-10), 129.5 (CH-8), 152.5 (C-6a), 164.6 (C-3a).