Benzazaborinines as novel bioisosteric replacements of naphthalene: Propranolol as an example

Journal of Medicinal Chemistry

Volumn 58, Issue 23, 2015, Pages 9287-9295

  Rombouts, Frederik J R ^a   Tovar, Fulgencio ^b   Austin, Nigel ^a   Tresadern, Gary ^a   Trabanco, Andrés A ^c  

^a JANSSEN RESEARCH AND DEVELOPMENT   (Belgium)

^b Eurofins Villapharma Research   (Spain)

^c Janssen Cilag SA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

1 ISOPROPYLAMINO 3 [(2 METHYL 1,2 DIHYDRO BENZO[E][1,2]AZABORININ 5 YL)OXY] PROPAN 2 OL; 1 ISOPROPYLAMINO 3 [(2 METHYL 1,2 DIHYDRO BENZO[E][1,2]AZABORININ 8 YL)OXY] PROPAN 2 OL; 1 METHOXY 2 NITRO 3 VINYLBENZENE; 2 BROMO 3 METHOXYANILINE; 2 METHOXY 6 VINYLANILINE; 2 METHYL 1,2 DIHYDRO BENZO[E][1,2]AZABORININ 5 OL; 2 METHYL 5 OXIRAN 2 YLMETHOXY 1,2 DIHYDRO BENZO[E][1,2]AZABORININE; 3 METHOXY 2 VINYLANILINE; 5 METHOXY 2 METHYL 1,2 DIHYDRO BENZO[E][1,2]AZABORININE; 8 METHOXY 2 METHYL 1,2 DIHYDROBENZO[E][1,2]AZABORININE; AROMATIC COMPOUND; BENZAZABORININE DERIVATIVE; NAPHTHALENE; PROPRANOLOL; UNCLASSIFIED DRUG; BENZENE DERIVATIVE; BETA ADRENERGIC RECEPTOR BLOCKING AGENT; BORINIC ACID DERIVATIVE; HETEROCYCLIC COMPOUND;

ANIMAL TISSUE; ARTICLE; COMPARATIVE STUDY; DRUG BIOAVAILABILITY; DRUG POTENCY; DRUG SYNTHESIS; HUMAN; HUMAN CELL; IN VITRO STUDY; IN VIVO STUDY; MOUSE; NONHUMAN; PHYSICAL CHEMISTRY; RAT; ANALOGS AND DERIVATIVES; ANIMAL; BIOAVAILABILITY; BRAIN; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; CHO CELL LINE; CRICETULUS; DRUG DESIGN; DRUG STABILITY; METABOLISM;

ADRENERGIC BETA-ANTAGONISTS; ANIMALS; AZA COMPOUNDS; BENZENE DERIVATIVES; BIOLOGICAL AVAILABILITY; BORINIC ACIDS; BRAIN; CELL LINE; CHO CELLS; CRICETULUS; DRUG DESIGN; DRUG STABILITY; HUMANS; MICE; MODELS, MOLECULAR; PROPRANOLOL; RATS;

EID: 84949895040     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/acs.jmedchem.5b01088     Document Type: Article

References (33)

1. Brown, N., Ed. Bioisosteres in Medicinal Chemistry; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany, 2012.
2. Meanwell, N. A. Synopsis of some recent tactical application of bioisosteres in drug design J. Med. Chem. 2011, 54, 2529-2591 10.1021/jm1013693
3. Kennewell, E. A.; Willett, P.; Ducrot, P.; Luttmann, C. Identification of target-specific bioisosteric fragments from ligand-protein crystallographic data J. Comput.-Aided Mol. Des. 2006, 20, 385-394 10.1007/s10822-006-9072-0
4. Patani, G. A.; LaVoie, E. J. Bioisosterism: a rational approach in drug design Chem. Rev. 1996, 96, 3147-3176 10.1021/cr950066q
5. Lima, L. M.; Barreiro, E. J. Bioisosterism: a useful strategy for molecular modification and drug design Curr. Med. Chem. 2005, 12, 23-49 10.2174/0929867053363540
6. Wirth, M.; Zoete, V.; Michielin, O.; Sauer, W. H. B. SwissBioisostere: a database of molecular replacements for ligand design Nucleic Acids Res. 2013, 41, D1137-D1143 10.1093/nar/gks1059
7. Weber, J.; Achenbach, J.; Moser, D.; Proschak, E. VAMMPIRE: A Matched Molecular Pairs Database for Structure-Based Drug Design and Optimization J. Med. Chem. 2013, 56, 5203-5207 10.1021/jm400223y
8. Posy, S. L.; Claus, B. L.; Pokross, M. E.; Johnson, S. R. 3D Matched Pairs: Integrating Ligand- and Structure-Based Knowledge for Ligand Design and Receptor Annotation J. Chem. Inf. Model. 2013, 53, 1576-1588 10.1021/ci400201k
9. Papadatos, G.; Brown, N. In silico applications of bioisosterism in contemporary medicinal chemistry practice WIREs Comput. Mol. Sci. 2013, 3, 339-354 10.1002/wcms.1148
10. A textbook example is the marketed drug 2-methyl-4-(4-methyl-1-piperazinyl)-10H-thieno[2,3-b][1,5]benzodiazepine (olanzapine), which has a similar pharmacological profile to its benzene analogue 8-chloro-11-(4-methylpiperazin-1-yl)-5H-dibenzo[b,e][1,4]diazepine (clozapine), see Citrome, L. A systematic review of meta-analyses of the efficacy of oral atypical antipsychotics for the treatment of adult patients with schizophrenia Expert Opin. Pharmacother. 2012, 13, 1545-1573 10.1517/14656566.2011.626769
11. Burger, A. Isosterism and bioisosterism in drug design Prog. Drug Res. 1991, 37, 287-371 10.1007/978-3-0348-7139-6-7
12. Campbell, P. G.; Marwitz, A. J. V.; Liu, S. Y. Recent advances in azaborine chemistry Angew. Chem., Int. Ed. 2012, 51, 6074-6092 10.1002/anie.201200063
13. Bosdet, M. J. D.; Piers, W. E. B-N as a C-C substitute in aromatic systems Can. J. Chem. 2009, 87, 8-29 10.1139/v08-110
14. Abbey, E. R.; Zakharov, L. N.; Liu, S. Y. Boron in Disguise: The parent "fused" BN indole J. Am. Chem. Soc. 2011, 133, 11508-11511 10.1021/ja205779b
15. Brown, A. N.; Zakharov, L. N.; Mikulas, T.; Dixon, D. A.; Liu, S. Y. Rhodium-catalyzed B-H activation of 1,2-azaborines: synthesis and characterization of BN isosteres of stilbenes Org. Lett. 2014, 16, 3340-3343 10.1021/ol501362w
16. Wisniewski, S. R.; Guenther, C. L.; Argintaru, O. A.; Molander, G. A. A convergent, modular approach to functionalized 2,1-borazaronaphthalenes from 2-aminostyrenes and potassium organotrifluoroborates J. Org. Chem. 2014, 79, 365-378 10.1021/jo402616w
17. Sun, F. Y.; Lv, L. L.; Huang, M.; Zhou, Z. H.; Fang, X. D. Palladium-catalyzed cross-coupling reactions of 4a,8a-azaboranaphthalene Org. Lett. 2014, 16, 5024-5027 10.1021/ol502339h
18. Liu, X.; Wu, P.; Li, J.; Cui, C. Synthesis of 1,2-borazaronaphthalenes from imines by base-promoted borylation of C-H bond J. Org. Chem. 2015, 80, 3737-3744 10.1021/jo5029437
19. Sánchez Casado, M. R.; Ciordia Jiménez, M.; Ariza Bueno, M.; Barriol, M.; Leenaerts, J. E.; Pagliuca, C.; Martínez Lamenca, C.; De Lucas, A. I.; García, A.; Trabanco, A. A.; Rombouts, F. J. R. Synthesis of 2,1-borazaroquinolines and 2,1-borazaroisoquinolines from vinylaminopyridines and potassium organotrifluoroborates by microwave-assisted heating Eur. J. Org. Chem. 2015, 2015, 5221-5229 10.1002/ejoc.201500622
20. Knack, D. H.; Marshall, J. L.; Harlow, G. P.; Dudzik, A.; Szaleniec, M.; Liu, S. Y.; Heider, J. BN/CC isosteric compounds as enzyme inhibitors: N- and B-ethyl-1,2-azaborine inhibit ethylbenzene hydroxylation as nonconvertible substrate analogues Angew. Chem., Int. Ed. 2013, 52, 2599-2601 10.1002/anie.201208351
21. Vlasceanu, A.; Jessing, M.; Kilburn, J. P. BN/CC isosterism in borazaronaphthalenes towards phosphodiesterase 10A (PDE10A) inhibitors Bioorg. Med. Chem. 2015, 23, 4453-4461 10.1016/j.bmc.2015.06.019
22. Black, J. W.; Crowther, A. F.; Shanks, R. G.; Smith, L. H.; Dornhorst, A. C. A new adrenergic beta-receptor antagonist Lancet 1964, 283, 1080-1081 10.1016/S0140-6736(64)91275-9
23. Molander, G. A.; Bernardi, C. R. Suzuki-Miyaura cross-coupling reactions of potassium alkenyltrifluoroborates J. Org. Chem. 2002, 67, 8424-8429 10.1021/jo026236y
24. ADMET Predictor version 6, Simulations Plus, Inc., 42505 10th Street West, Lancaster, California 93534-7059, USA. http://www.simulations-plus.com/ (accessed November 3, 2015).
25. Di, L.; Umland, J. P.; Chang, G.; Huang, Y.; Lin, Z.; Scott, D. O.; Troutman, M. D.; Liston, T. E. Species independence in brain tissue binding using brain homogenates Drug Metab. Dispos. 2011, 39, 1270-1277 10.1124/dmd.111.038778
26. Peterson, L. A. Reactive metabolites in the biotransformation of molecules containing a furan ring Chem. Res. Toxicol. 2013, 26, 6-25 10.1021/tx3003824
27. Abraham, V. C.; Towne, D. L.; Waring, J. F.; Warrior, U.; Burns, D. J. Application of a high-content multiparameter cytotoxicity assay to prioritize compounds based on toxicity potential in humans J. Biomol. Screening 2008, 13, 527-537 10.1177/1087057108318428
28. O'Brien, P. J.; Irwin, W.; Diaz, D.; Howard-Cofield, E.; Krejsa, C. M.; Slaughter, M. R.; Gao, B.; Kaludercic, N.; Angeline, A.; Bernardi, P.; Brain, P.; Hougham, C. High concordance of drug-induced human hepatotoxicity with in vitro cytotoxicity measured in a novel cell-based model using high content screening Arch. Toxicol. 2006, 80, 580-604 10.1007/s00204-006-0091-3
29. All in vivo experimental procedures were performed according to the applicable European Communities Council Directive of November 24, 1986 (86/609/EEC) and approved by the Animal Care and Use Committee of Janssen Pharmaceutical Companies of Johnson & Johnson and by the local ethical committee.
30. Yan, H. Stereoselective transport of drugs across the blood-brain barrier (BBB) in vivo and in vitro. Pharmacokinetic and pharmacodynamic studies of the (S)- and (R)-enantiomers of different 5-HT1A receptor agonists and antagonists. Comprehensive Summaries of Uppsala Dissertations from the Faculty of Medicine 1138: Uppsala, 2002.
31. Bikiaris, D.; Koutris, E.; Karavas, E. New Aspects in Sustained Drug Release Formulations Recent Pat. Drug Delivery Formulation 2007, 1, 201-213 10.2174/187221107782331629
32. Sirius Analytical Ltd., Forest Row BusinessPark, StationRoad, Forest Row, East Sussex. RH18 5DW, UK. http://www.sirius-analytical.com/ (accessed July 12, 2015).
33. Arisawa, M.; Terada, Y.; Takahashi, K.; Nakagawa, M.; Nishida, A. Development of isomerization and cycloisomerization with use of a ruthenium hydride with N-heterocyclic carbene and its application to the synthesis of heterocycles J. Org. Chem. 2006, 71, 4255-4261 10.1021/jo060308u