5256
N. Terzioglu et al. / Bioorg. Med. Chem. Lett. 14 (2004) 5251–5256
1
1
1
0. Hashimoto, T.; Harusawa, S.; Araki, L.; Zuiderveld, O.
P.; Smit, M. J.; Imazu, T.; Takashima, S.; Yamamoto, Y.;
Sakamoto, Y.; Kurihara, T.; Leurs, R.; Bakker, R. A.;
22. Passarella, D.; Favia, R.; Giardini, A.; Lesma, G.;
Martinelli, M.; Silvani, A.; Danieli, B.; Efange, S. M.
N.; Mash, D. C. Ibogaine Analogues. Synthesis and
Preliminary Pharmacological Evaluation of 7-Heteroaryl-
2-azabicyclo[2.2.2]oct-7-enes. Bioorg. Med. Chem. 2003,
11, 1007–1014.
23. Louvet, P.; Lallement, G.; Pernot-Marino, I.; Luu-Duc,
C.; Blanchet, G. Novel Benzimidazoles as Ligands for the
Stychnine-Insensitive N-methyl-D-aspartate-Linked Gly-
cine Receptor. Arch. Pharm. Pharm. Med. Chem. 2000,
333, 123–129.
24. Dannhardt, G.; Kohl, B. K. Benzimidazoles as NMDA
Glycine-Site Antagonists: Study on Structural Require-
ments in 2-Position of the Ligands. Eur. J. Med. Chem.
1993, 28, 71–75.
25. Battagliaa, S.; Boldrinib, E.; Da Settimoa, F.; Dondioc,
G.; La Mottaa, C.; Marinia, A. M.; Primofiorea, G.
Indole Amide Derivatives: Synthesis, Structure–Activity
Relationships and Molecular Modelling Studies of a New
Yamatodani, A. A Selective Human H(
ist:
(ꢀ)-2-Cyano-1-methyl-3-{(2R,5R)-5-[1H-imidazol-
(5)-yl]tetrahydrofuran-2-yl}methylguanidine. J. Med.
4
)-Receptor Agon-
4
Chem. 2003, 46, 3162–3165.
1. Jablonowski, J. A.; Grice, C. A.; Chai, W.; Dvorak, C. A.;
Venable, J. D.; Kwok, A. K.; Ly, K. S.; Wei, J.; Baker, S.
M.; Desai, P. J.; Jiang, W.; Wilson, S. J.; Thurmond, R.
L.; Karlson, L.; Edwards, J. P.; Lovenberg, T. W.;
Carruthers, N. I. The First Potent and Selective Non-
4
Imidazole Human Histamine H Receptor Antagonists. J.
Med. Chem. 2003, 46, 3957–3960.
2. Romero, D. L.; Morge, R. A.; Biles, C.; Berrios-Pena, N.;
May, P. D.; Palmer, J. R.; Johnson, P. D.; Smith, H. W.;
Busso, M.; Tan, C.; Voorman, R. L.; Reusser, F.; Althaus,
I. W.; Downey, K. M.; So, A. G.; Resnick, L.; Tarpley, W.
G.; Aristoff, P. A. Discovery, Synthesis, and Bioactivity of
Bis(heteroaryl)piperazines.1. A Novel Class of Non-
Nucleoside HIV-1 Reverse Transcriptase Inhibitors. J.
Med. Chem. 1994, 37, 999–1014.
1
Series of Histamine H -Receptor Antagonists. Eur. J.
Med. Chem. 1999, 34, 93–105.
26. Ponasik, J. A.; Conova, S.; Kinghorn, D.; Kinney, W. A.;
Rittschof, D.; Ganem, B. Pseudoceratidine, A Marine
Natural Product with Antifouling Activity: Synthetic and
Biological Studies. Tetrahedron 1998, 54, 6977–6986.
27. Lee, I. H.; Jeoung, E. H.; Kreevoy, M. M. Marcus Theory
of a Parallel Effect on R for Hydride Transfer Reaction
Between NAD+ Analogues. J. Am. Chem. Soc. 1997, 119,
2722–2728.
1
1
3. Suziki, H.; Kondo, A.; Ogawa, T. Preparation of Aro-
matic Iodides from Bromides via The Reverse Halogen
Exchange. Chem. Lett. 1985, 411–412.
4. Sabelle, S.; Renard, P.-Y.; Pecorella, K.; Suzzoni-Dezard,
S.; Creminon, C.; Grassi, J.; Mioskowski, C. Design and
Synthesis of Chemiluminescent Probes for the Detection
of Cholinesterase Activity. J. Am. Chem. Soc. 2002, 124,
4
874–4880.
28. Ohemengt, K. A.; Roth, B. Receptor-Based Design of
Novel Dihydrofolate Reductase Inhibitors: Benzimidazole
and Indole Derivatives. J. Med. Chem. 1991, 34, 1383–
1394.
1
1
5. Bennasar, M. L.; Vidal, B.; Bosch, J. Biomimetic Total
Synthesis of Ervitsine and Indole Alkaloids of the Erva-
tamine Group via 1,4-Dihydropyridines. J. Org. Chem.
1
997, 62, 3597–3609.
29. Matsuno, K.; Ichimura, M.; Nakajima, T.; Tahara, K.;
Fujiwara, S.; Kase, H.; Ushiki, J.; Geise, N. A.; Pandey,
A.; Scarborough, R. M.; Lokker, N. A.; Yu, J.-C.; Irie, J.;
Tsukuda, E.; Ide, S.; Oda, S.; Nomoto, Y. Potent and
Selective Inhibitors of Platelet-Derived Growth Factor
Receptor Phosphorylation. 1. Synthesis, Structure–Activ-
ity Relationship, and Biological Effect of a New Class of
Quinazoline Derivatives. J. Med. Chem. 2002, 45, 3057–
3066.
6. Labadie, S. S.; Teng, E. Indol-2-yltributylstannane: A
Versatile Reagent for 2-Substituted Indoles. J. Org. Chem.
1994, 59, 4250–4254.
1
1
7. Brehm, W. J. Derivatives on Indole-2-Carboxylic Acid.
J. Am. Chem. Soc. 1949, 71, 3541–3542.
8. Luca, L.; Giacomelli, G.; Porcheddu, A. A Mild and
Efficient Alternative to the Classical Swern Oxidation.
J. Org. Chem. 2001, 66, 7907–7909.
1
9. Omura, K.; Swern, D. Oxidation of Alcohols by ꢁActi-
vatedꢀ Dimethyl sulfoxide. A Preparative Steric and
Mechanistic Study. Tetrahedron 1978, 34, 1651–1660.
0. Ashton, M. J.; Ashford, A.; Loveless, A. H.; Riddell, D.;
Salmon, J.; Stevenson, G. V. W. Heterocyclic Analogues
of Chlorcyclizine with Potent Hypolipidemic Activity.
J. Med. Chem. 1984, 27, 1245–1253.
30. Bradford, M. A Rapid and Sensitive Method for the
Quantitation of Microgram Quantities of Protein Utilizing
the Principle of Protein-Dye Binding. Anal. Biochem.
1976, 72, 248–254.
31. Carruthers, N. I.; Dvorak, C. A.; Edwards, J. P.; Grice, C.
A.; Jablonowski, J. A.; Ly, K. S.; Pio, B. A.; Shah, C. R.;
Venable, J. D. Preparation of Nitrogen Containing
Heterocyclic Compounds as Compounds Useful for in
the Treatment of Histamine H4 Receptor Mediated
Diseases. PCT Int. Appl. (2004), 70 pp. CODEN:
PIXXD2 WO 2004022060 A2 20040318 Application:
WO 2003-US27461 20030904. Priority: US 2002-408569
20020906. CAN 140:270852 AN 2004:220205 CAPLUS.
2
2
1. Kitbunnadaj, R.; Zuiderveld, O. P.; De Esch, I. J. P.;
Vollinga, R. C.; Bakker, R.; Lutz, M.; Spek, A. L.; Cavoy,
E.; Deltent, M.-F.; Menge, W. M. P. B.; Timmerman, H.;
Leurs, R. Synthesis and Structure–Activity Relationships
3
of Conformationally Constrained Histamine H Receptor
Agonists. J. Med. Chem. 2003, 46, 5445–5457.