Novel 3-aroylpyrazolo[5,1-c][1,2,4]benzotriazine 5-oxides 8-substituted, ligands at GABAA/benzodiazepine receptor complex: Synthesis, pharmacological and molecular modeling studies

Bioorganic and Medicinal Chemistry

Volumn 16, Issue 8, 2008, Pages 4471-4489

  Guerrini, Gabriella ^a   Ciciani, Giovanna ^a   Cambi, Giovanni ^a   Bruni, Fabrizio ^a   Selleri, Silvia ^a   Melani, Fabrizio ^a   Montali, Marina ^b   Martini, Claudia ^b   Ghelardini, Carla ^a   Norcini, Monica ^a   Costanzo, Annarella ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF PISA   (Italy)

Author keywords

3 Acyl derivatives pyrazolo 5,1 c 1,2,4 benzotriazine 5 oxides; GABAA benzodiazepine receptor ligands; Tricyclic heteroaromatic system

Indexed keywords

1,2,4 BENZOTRIAZINE DERIVATIVE; 3 (1 METHYL 1H PYRROL 2 YLCARBONYL) 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1 METHYL 1H PYRROL 2 YLCARBONYL) 8 ETHOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1 METHYL 1H PYRROL 2 YLCARBONYL) 8 PHENOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1,3 BENZODIOXOL 5 YLCARBONYL) 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1H PYRROL 2 YLCARBONYL) 8 CHLOROPYRAZOLO[5,1 C][1,2,4] BENZOTRIAZINE 5 OXIDE; 3 (1H PYRROL 2 YLCARBONYL) 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE; 3 (1H PYRROL 2 YLCARBONYL) 8 ETHOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (1H PYRROL 2 YLCARBONYL) 8 PHENOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (2 METHOXYBENZOYL) 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (4 METHOXYBENZOYL) 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (4 METHOXYBENZOYL) 8 ETHOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (FUR 2 YLCARBONYL) 8 BENZYLOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (FUR 2 YLCARBONYL) 8 CHLOROPYRAZOLO[5,1,C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (FUR 2 YLCARBONYL) 8 ETHOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (FUR 2 YLCARBONYL) 8 PHENOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (FUR 2 YLCARBONYL) 8 PROPARGYLOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (PYRIDIN 3 YLCARBONYL) 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (PYRIDIN 3 YLCARBONYL) 8 ETHOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (THIEN 2 YLCARBONYL) 8 BENZYLOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (THIEN 2 YLCARBONYL) 8 ETHOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (THIEN 2 YLCARBONYL) 8 PHENOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE; 3 (THIEN 2 YLCARBONYL) 8 PHENOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 (THIEN 3 YLCARBONYL) 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 ACETYL 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 ACETYL 8 ETHOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 ACETYL 8 PHENOXYPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 BENZOYL 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; 3 FORMYL 8 CHLOROPYRAZOLO[5,1 C][1,2,4]BENZOTRIAZINE 5 OXIDE; DIAZEPAM; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTICONVULSANT ACTIVITY; ARTICLE; BINDING AFFINITY; CONTROLLED STUDY; DRUG BINDING; DRUG DOSE COMPARISON; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROGEN BOND; IN VIVO STUDY; LEARNING; LIGAND BINDING; MEMORY; MOLECULAR MODEL; MOTOR ACTIVITY; MOTOR COORDINATION; MOUSE; NONHUMAN; SLEEP TIME; TRANQUILIZING ACTIVITY;

ANIMALS; ANXIETY; BEHAVIOR, ANIMAL; ETHANOL; LIGANDS; MALE; MEMORY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; OXIDES; PYRAZOLES; RATS; RECEPTORS, GABA-A; SEIZURES; SLEEP; STRUCTURE-ACTIVITY RELATIONSHIP; TIME FACTORS; TRIAZINES;

EID: 42249107126     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2008.02.058     Document Type: Article

References (59)

1. Minier F., and Sigel E. PNAS 101 (2004) 7769-7774
2. Rudolph U., and Mohler H. Curr. Opin. Pharmacol. 6 (2006) 1-6
3. Cooke A.J., and Hamilton N.M. Expert Opin. Ther. Patents 12 (2002) 1491-1501
4. Dawson G.R., Collinson N., and Atack J.R. CNS Spectr. 10 (2005) 21-27
5. Rudolph U., and Mohler H. Annu. Rev. Pharmacol. Toxicol. 44 (2004) 475-498
6. Atack J.R. Expert Opin. Invest. Drugs 14 (2005) 601-618
7. Morris H.V., Dawson G.R., Reynolds D.S., Atack J.R., and Stephens D.N. Eur. J. Neurosci. 23 (2006) 2495-2504
8. Sieghart W. Adv. Pharmacol. 54 (2006) 231-263
9. Basile A.S., Lippa A.S., and Skolnick P. Drug Discovery Today: Ther. Strateg. 3 (2006) 475-481
10. Whiting P.J. Curr. Opin. Pharmacol. 6 (2006) 24-29
11. Savic M.M., Obradovic D.I., Ugresic N.D., and Bokonjic D.R. Neural Plast. 12 (2005) 289-298
12. Dias R., Sheppard W.F.A., Fradley R.L., Garrett E.M., Stanley J.L., Tye S.J., Goodacre S., Lincoln R.J., Cook S.M., Conley R., Hallett D., Humphries A.C., Thompson S.A., Wafford K.A., Street L.J., Castro J.L., Whiting P.J., Rosahl T.W., Atack J.R., McKernan R.M., Dawson G.R., and Reynolds D.S. J. Neurosci. 25 (2005) 10682-10688
13. Dawson G.R., Maubach K., Collinson N., Cobain M., Everitt B.J., MacLeod A.M., Choudhury H.I., McDonald L.M., Pillai G.V., Rycroft W., Smith A.J., Sternfeld F., Tattersall D., Wafford K.A., Reynolds D.S., Seabrook G., and Atack J.R. JPET 316 (2006) 1335-1345
14. Maubach K. Drugs Future 31 (2006) 151-162
15. McKay P.F., Foster K.L., Mason D., Cummings R., Garcia M., Williams L.S., Grey C., McCane S., He X., Cook J.M., and June H.L. Psycopharmacology 172 (2004) 455-462
16. Kloda J.H., and Czajkowski C. Mol. Pharmacol. 71 (2007) 483-493
17. Campo-Soria C., Chang Y., and Weiss D.S. Br. J. Pharmacol. 148 (2006) 984-990
18. Jones-Davis D.M., Song L., Gallagher M.J., and Macdonald R.L. J. Neurosci. 25 (2005) 8056-8065
19. Costanzo A., Guerrini G., Ciciani G., Bruni F., Selleri S., Costa B., Martini C., Lucacchini A., Malmberg-Aiello P., and Ipponi A. J. Med. Chem. 42 (1999) 2218-2226
20. Costanzo A., Guerrini G., Ciciani G., Bruni F., Selleri S., Costa B., Martini C., Lucacchini A., Malmberg-Aiello P., and Ipponi A. Med. Chem. Res. 9 (1999) 322-339
21. Costanzo A., Guerrini G., Ciciani G., Bruni F., Costagli C., Selleri S., Costa B., Martini C., and Malmberg-Aiello P. Med. Chem. Res. 10 (2001) 366-377
22. Costanzo A., Guerrini G., Ciciani G., Bruni F., Costagli C., Selleri S., Besnard F., Costa B., Martini C., and Malmberg-Aiello P. J. Med. Chem. 45 (2002) 5710-5720
23. Sullivan S.K., Petroski R.E., Verge G., Gross R.S., Foster A.C., and Grigoriadis D.E. J. Pharmacol. Exp. Ther. 311 (2004) 537-546
24. Petroski R.E., Pomeroy J.E., Das R., Bowman H., Yang W., Chen A.P., and Foster A.C. J. Pharmacol. Exp. Ther. 317 (2006) 369-377
25. Lippa A.S., Czobor P., Stark J., Beer B., Kostakis E., Gravielle M., Bandypadhyay S., Russek S.J., Gibbs T.T., Farb D.H., and Skolnick P. PNAS 102 (2005) 7380-7385
26. Ebert B., Wafford K.A., and Deacon S. Pharmacol. Ther. 112 (2006) 612-629
27. Ebert B., and Wafford K.A. Drug Discovery Today: Ther. Strateg. 3 (2006) 547-554
28. Hoepping A., Scheunemann M., Fischer S., Deuter-Conrad W., Hiller A., Wegner F., Diekers M., Steinbach J., and Brust P. Nucl. Med. Biol. 34 (2007) 559-570
29. Guerrini G., Costanzo A., Ciciani G., Bruni F., Selleri S., Costagli C., Besnard F., Costa B., Martini C., De Siena G., and Malmberg-Aiello P. Bioorg. Med. Chem. 14 (2006) 758-775
30. Costanzo A., Guerrini G., Bruni F., and Selleri S. J. Heterocycl. Chem. 31 (1994) 1369-1376
31. Lindley J.M., McRobbie I.M., Meth-Chon O., and Suschitzky H. J. Chem. Soc., Perkin Trans 1 (1980) 982-994
32. Milata V., Ilavsky D., Goljer I., Lesko J., Chahinian M., and Henrt-Basch E. Collect. Czech. Chem. Commun. 55 (1990) 1038-1048
33. Tomcufcik, A. S.; Dusza, J. P. EP0129846, JP1985013764, 1984.
34. Tomcufcik, A. S.; Dusza, J .P. US 4,980,472, 1990.
35. Dusza, J. P.; Tomcufcik, A. S.; Albight, J. D. DE3422844, EP0129847., 1984.
36. Dusza, J. P.; Tomcufcik, A. S.; Albight, J. D.; Beer, B. US 0198221, 2002.
37. Starks M.C., and Liotta C. Phase Transfer Catalysis, Principles and Techniques (1978), Academic Press, Inc., London Ltd
38. Guerrini G., Costanzo A., Bruni F., Selleri S., Casilli M.L., Giusti L., Martini C., Lucacchini A., Malmberg Aiello P., and Ipponi A. Eur. J. Med. Chem. 31 (1996) 259-272
39. Primofiore G., Da Settimo F., Marini A.M., Taliani S., La Motta C., Simorini F., Novellino E., Greco G., Cosimelli B., Ehlardo M., Sala A., Besnard F., Montali M., and Martini C. J. Med. Chem. 49 (2006) 2489-2495
40. Guerrini G., Ciciani G., Cambi G., Bruni F., Selleri S., Besnard F., Montali M., Martini C., Ghelardini C., Galeotti N., and Costanzo A. Bioorg. Med. Chem. 15 (2007) 2573-2586
41. Ernst M., Brauchart D., Boresch S., and Sieghart W. Neuroscience 119 (2003) 933-943
42. Ernst M., Bruckner S., Boresch S., and Sieghart W. Mol. Pharmacol. 68 (2005) 1291-1300
43. Ernst, M. http://www.univie.ac.at/brainresearch/links/mceDownload.htm, 2003.
44. Renard S., Olivier A., Granger P., Avenet P., Graham D., Sevrin M., George P., and Besnard F. J. Biol. Chem. 274 (1999) 13370-13374
45. Cromer B.A., Morton C.J., and Parker M.W. TiBS 27 (2002) 280-287
46. Kucken A.M., Teissere J.A., Seffinga-Clark J., Wagner D.A., and Czajkowski C. Mol. Pharmacol. 63 (2003) 289-296
47. Chou K.-C. Biochem. Biophys. Res. Commun. 316 (2004) 636-642
48. Wafford K.A. Curr. Opin. Pharmacol. 5 (2005) 47-52
49. Szarics E., Riedl Z., Nyikos L., Hajos G., and Kardos J. Eur. J. Med. Chem. 41 (2006) 445-456
50. Sarto-Jackson I., Ramerstorfer J., Ernst M., and Sieghart W. J. Neurochem. 96 (2006) 983-995
51. Zhang W., Koehler K.F., Zhang P., and Cook J.M. Drug Des. Discovery 12 (1995) 193-248
52. Xiaohui H., Qi H., Chunrong M., Shu Y., and McKernan R.C.J.M. Drug Des. Discovery 17 (2000) 131-171
53. Qi H., Xiaohui H., Chunrong M., Ruiyan L., Shu Y., Dayer C.A., Wenger G.R., McKernan R., and Cook J.M. J. Med. Chem. 43 (2000) 71-95
54. Khanberg P., Howard M.H., Liljefors T., Nielsen M., Nielsen E.O., Sterner O., and Pettersson I. J. Mol. Graphics Modell. 23 (2004) 25-261
55. Tauber M., Calame-Droz E., Prut L., Rudolph U., and Crestani F. Eur. J. Neurosci. 18 (2003) 2599-2604
56. Savic M.M., Obradovic D.I., Ugresic N.D., Cook J.M., Yin W., and Bokonjic D.R. Behav. Brain Res. 158 (2005) 293-300
57. Martini C., Lucacchini A., Ronca G., Hrelia S., and Rossi C.A. J. Neurochem. 38 (1982) 15-19
58. Jarvik M.E., and Kopp R. Psychol. Rep. 21 (1967) 221-224
59. Accelrys Insight II: Accelrys, Inc. San Diego, CA.