Antagonists of 5-HT 6 receptors. Substituted 3-(phenylsulfonyl) pyrazolo[1,5-a]pyrido[3,4-e]pyrimidines and 3-(phenylsulfonyl)pyrazolo[1,5-a] pyrido[4,3-d]pyrimidines - Synthesis and 'structure-activity' relationship

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 13, 2012, Pages 4273-4280

  Ivachtchenko, Alexandre V ^a,b   Golovina, Elena S ^a   Kadieva, Madina G ^a   Kysil, Volodymyr M ^b   Mitkin, Oleg D ^a   Vorobiev, Anton A ^a   Okun, Ilya ^b  

^a Chemical Diversity Research Institute   (Russian Federation)

^b CHEMDIV INC   (United States)

Author keywords

Antagonists; hERG channel; Phenylsulfonyl pyrazolo pyrido pyrimidines; Serotonin receptor 5 HT 6; Specificity

Indexed keywords

3 (PHENYLSULFONYL)PYRAZOLO[1,5 A]PYRIDO[3,4 E]PYRIMIDINE DERIVATIVE; 3 (PHENYLSULFONYL)PYRAZOLO[1,5 A]PYRIDO[4,3 D]PYRIMIDINE DERIVATIVE; POTASSIUM CHANNEL HERG; PYRAZOLO[1,5 A]PYRIMIDINE DERIVATIVE; SEROTONIN 2B RECEPTOR; SEROTONIN 6 ANTAGONIST; UNCLASSIFIED DRUG;

ARTICLE; CALCIUM MOBILIZATION; CELL STRAIN HEK293; CONCENTRATION RESPONSE; CONTROLLED STUDY; CRYSTAL STRUCTURE; DRUG POTENCY; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; IC 50; STRUCTURE ACTIVITY RELATION;

CRYSTALLOGRAPHY, X-RAY; ETHER-A-GO-GO POTASSIUM CHANNELS; HYDROGEN BONDING; ISOMERISM; MOLECULAR CONFORMATION; PROTEIN BINDING; PYRAZOLES; PYRIMIDINES; RECEPTORS, SEROTONIN; SEROTONIN ANTAGONISTS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 84862234229     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2012.05.036     Document Type: Article

References (26)

1. X. Codony, J.M. Vela, and M.J. Ramírez Curr. Opin. Pharmacol. 11 2011 1
2. F. Borsini Pharmacology of 5-HT6 receptors, Part I, (International Review of Neurobiology) Vol. 95 2010 Academic Press 211
3. F. Borsini Pharmacology of 5-HT6 receptors, Part II, (International Review of Neurobiology) Vol. 96 2010 Academic Press 242
4. A.V. Ivachtchenko, Y.A. Ivanenkov, and S.E. Tkachenko Exp. Opin. Ther. Patents 20 2010 1247
5. Macauley, D. Abstracts of American Chemical Society. 239th national meeting-Investigating new therapeutic candidates: part 1. 21-25 March 2010, San Francisco, CA, USA. IDrugs. 2010 May;13(5):289.
6. http://clinicaltrials.gov/archive/NCT00895895/2011-08-10.
7. Thomson Reuters Drug News. December 1, 2009. (NCT01019421) ClinicalTrials.gov Web Site 2009
8. Thomson Reuters Drug News. December 1, 2009.
9. Arnt, J.; Bang-Andersen, B.; Bymaster, F. P. Abstracts of 27th World Congr CINP (June 6-10, Hong Kong) 2010, P-04.003.
10. http://www.avineuro.com/avineuro-pharmaceuticals-inc-reports-positive- phase-i-clinical-trial-results-on-avn-322-potent-small-molecule-for-treatment- of-alzheimer%e2%80%99s-disease/.
11. Tkachenko, S.; Ivachtchenko, A.; Khvat, A.; Okun, I. Abstracts of 9th Int Conf. Alzheimer Parkinson Dis. (AD/PD), (March 11-15, Prague) 2009.
12. Ivachtchenko, A. V.; Kysil V. M., Ivachtchenko, A. A.; Savchuk, N. P. RU Patent 239134.
13. Ivachtchenko, A. V.; Savchuk, N. P.; Ivachtchenko, A. A. WO Patent, 136814, 2009.
14. http://www.avineuro.com/avineuro-pharmaceuticals-inc-reports-positive- phase-2a-clinical-proof-of-concept-trial-results-on-avn-211-potent-small- molecule-for-treatment-of-schizophrenia.
15. Ivachtchenko, A. V.; Savchuk, N. P.; Ivachtchenko, A. A. RU Patent 2369600.
16. Ivachtchenko, A. V.; Savchuk, N. P.; Ivachtchenko, A. A. WO Patent, 093206, 2009.
17. A.V. Ivachtchenko, D.D. Dmitriev, E.S. Golovina, E.S. Dubrovskaya, M.G. Kadieva, A.G. Koryakova, V.M. Kysil, O.D. Mitkin, S.E. Tkachenko, I.M. Okun, and A.A. Vorobiov Bioorg. Med. Chem. Lett. 20 2010 2133
18. A.V. Ivachtchenko, D.D. Dmitriev, E.S. Golovina, M.G. Kadieva, A.G. Koryakova, V.M. Kysil, O.D. Mitkin, I.M. Okun, S.E. Tkachenko, and A.A. Vorobiov J. Med. Chem. 53 2010 5186
19. A.V. Ivachtchenko, E.S. Golovina, M.G. Kadieva, A.G. Koryakova, O.D. Mitkin, S.E. Tkachenko, V.M. Kysil, and I.M. Okun Eur. J. Med. Chem. 46 2011 1189
20. A.V. Ivachtchenko, E.S. Golovina, M.G. Kadieva, V.M. Kysil, O.D. Mitkin, S.E. Tkachenko, and I.M. Okun J. Med. Chem. 54 2011 8161
21. J. Holenz, R. Merce, J.L. Diá z, X. Guitart, X. Codony, A. Dordal, G. Romero, A. Torrens, J. Mas, B. Las Andaluz, S. Hernández, X. Monroy, E. Sánchez, E. Hernández, R. Pérez, R. Cubi, O. Sanfeliu, and H. Buschmann J. Med. Chem. 48 2005 1781
22. M.L. Ĺpez-Rodrigues, B. Benhamu, T. De la Fuente, A. Sanz, L. Pardo, and M. Campillo J. Med. Chem. 48 2005 4216
23. Y. Cheng, and W.H. Prusoff Biochem. Pharmacol. 22 1973 3099
24. R.B. Rothman, M.H. Baumann, J.E. Savage, L. Rauser, A. McBride, S.J. Hufeisen, and B.L. Roth Circulation 102 2000 2836
25. K.G. Shyu Circ. Res. 104 2009 1
26. N. Moss, Y. Choi, D. Cogan, A. Flegg, A. Kahrs, P. Loke, O. Meyn, R. Nagaraja, S. Napier, A. Parker, T. Peterson Jr., P. Ramsden, C. Sarko, D. Skow, J. Tomlinson, H. Tye, and M. Whitaker Bioorg. Med. Chem. Lett. 19 2009 2206