synthesis and structure-activity relationships at the histamine receptor subtypes
4.3.3 Summary and conclusion
4.4.2.4 Histamine H 2 R assay on the isolated spontaneously beating guinea pig right atrium 7
See section 3.4.2.5.
4.5 References
(1) Durant, G. J., Ganellin, C. R., Hills, D. W., Miles, P. D., Parsons, M. E., Pepper, E. S., White, G. R., The Histamine H2 Receptor Agonist Impromidine: Synthesis and Structure-Activity Considerations. J. Med. Chem. 1985, 28, 1414-1422.
(2) Durant, G. J., Duncan, W. A., Ganellin, C. R., Parsons, M. E., Blackmore, R. C., Rasmussen, A. C., Impromidine (SK&F 92676) is a very potent and specific agonist for histamine H2
receptors. Nature 1978, 276, 403-405.
(3) Buschauer, A., Synthesis and in Vitro Pharmacology of Arpromidine and Related Phenyl(pyridylalkyl)guanidines, a Potential New Class of Positive Inotropic Drugs. J. Med.
Chem. 1989, 32, 1963-1970.
(4) Buschauer, A., Friese-Kimmel, A., Baumann, G., Schunack, W., Synthesis and histamine H2
agonistic activity of arpromidine analogues: replacement of the pheniramine-like moiety by non-heterocyclic groups. Eur. J. Med. Chem. 1992, 27, 321-330.
(5) Xie, S.-X., Ghorai, P., Ye, Q.-Z., Buschauer, A., Seifert, R., Probing Ligand-Specific Histamine H1- and H2-Receptor Conformations with NG-Acylated Imidazolylpropylguanidines. J.
Pharmacol. Exp. Ther. 2006, 317, 139-146.
(6) Xie, S.-X., Kraus, A., Ghorai, P., Ye, Q.-Z., Elz, S., Buschauer, A., Seifert, R., N1 -(3-Cyclohexylbutanoyl)-N2-[3-(1H-imidazol-4-yl)propyl]guanidine (UR-AK57), a Potent Partial Agonist for the Human Histamine H1- and H2-Receptors. J. Pharmacol. Exp. Ther. 2006, 317, 1262-1268.
(7) Ghorai, P., Kraus, A., Keller, M., Götte, C., Igel, P., Schneider, E., Schnell, D., Bernhardt, G., Dove, S., Zabel, M., Elz, S., Seifert, R., Buschauer, A., Acylguanidines as Bioisosteres of Guanidines: NG-Acylated Imidazolylpropylguanidines, a New Class of Histamine H2 Receptor Agonists. J. Med. Chem. 2008, in press, DOI: 10.1021/jm800841w. Epub ahead of print on Oct 800825, 802008.
Structure-activity relationships of NG-acylated imidazolylalkylguanidines 161
(8) Sellier, C., Elz, S., Buschauer, A., Schunack, W., Histamine analogues:
imidazolylalkylguanidines, synthesis and in vitro pharmacology. Eur. J. Med. Chem. 1992, 27, 27-32.
(9) Lim, H. D., van Rijn, R. M., Ling, P., Bakker, R. A., Thurmond, R. L., Leurs, R., Evaluation of Histamine H1-, H2-, and H3-Receptor Ligands at the Human Histamine H4 Receptor:
Identification of 4-Methylhistamine as the First Potent and Selective H4 Receptor Agonist. J.
Pharmacol. Exp. Ther. 2005, 314, 1310-1321.
(10) Davey, D. D., Lumma, W. C., Convenient synthesis of 4-methylhistamine and racemic α, 4-dimethylhistamine and α,4-dimethylhistidine. J. Org. Chem. 1989, 54, 3211-3213.
(11) Henry, L., Nitro-alcohols. C. R. Hebd. Acad. Sci. 1895, 120, 1265-1268.
(12) Wadsworth, W. S., Emmons, W. D., The Utility of Phosphonate Carbanions in Olefin Synthesis. J. Am. Chem. Soc. 1961, 83, 1733-1738.
(13) Stark, H., Hüls, A., Ligneau, X., Purand, K., Pertz, H., Arrang, J.-M., Schwartz, J.-C., Schunack, W., Development of FUB 181, a Selective Histamine H3-Receptor Antagonist of High Oral in Vivo Potency with 4-(ω-(Arylalkyloxy)alkyl)-1H-imidazole Structure. Arch. Pharm.
(Weinheim). 1998, 331, 211-218.
(14) Friedman, L., Shechter, H., Preparation of Nitriles from Halides and Sodium Cyanide. An Advantageous Nucleophilic Displacement in Dimethyl Sulfoxide. J. Org. Chem. 1960, 25, 877-879.
(15) Zapf, C. W., Creighton, C. J., Tomioka, M., Goodman, M., A Novel Traceless Resin-Bound Guanidinylating Reagent for Secondary Amines To Prepare N,N-Disubstituted Guanidines.
Org. Lett. 2001, 3, 1133-1136.
(16) Feichtinger, K., Sings, H. L., Baker, T. J., Matthews, K., Goodman, M., Triurethane-Protected Guanidines and Triflyldiurethane-Protected Guanidines: New Reagents for Guanidinylation Reactions. J. Org. Chem. 1998, 63, 8432-8439.
(17) Feichtinger, K., Zapf, C., Sings, H. L., Goodman, M., Diprotected Triflylguanidines: A New Class of Guanidinylation Reagents. J. Org. Chem. 1998, 63, 3804-3805.
(18) Brennauer, A., Acylguanidines as bioisosteric groups in argininamide-type neuropeptide Y Y1
and Y2 receptor antagonists: synthesis, stability and pharmacological activity. Doctoral thesis, University of Regensburg, Germany 2006.
http://www.opus-bayern.de/uni-regensburg/frontdoor.php?source_opus=742&la=de.
(19) Mitsunobu, O., Yamada, M., Mukaiyama, T., Preparation of esters of phosphoric acid by the reaction of trivalent phosphorus compounds with diethyl azodicarboxylate in the presence of alcohols. Bull. Chem. Soc. Jpn. 1967, 40, 935-939.
(20) Paul, R., Anderson, G. W., N,N'-Carbonyldiimidazole, a New Peptide Forming Reagent. J.
Am. Chem. Soc. 1960, 82, 4596-4600.
(21) Paul, R., Anderson, G. W., N,N'-Carbonyldiimidazole in Peptide Synthesis. III. A Synthesis of Isoleucine-5 Angiotensin II Amide-I. J. Org. Chem. 1962, 27, 2094-2099.
(22) Kelley, M. T., Bürckstümmer, T., Wenzel-Seifert, K., Dove, S., Buschauer, A., Seifert, R., Distinct Interaction of Human and Guinea Pig Histamine H2-Receptor with Guanidine-Type Agonists. Mol. Pharmacol. 2001, 60, 1210-1225.
(23) Seifert, R., Wenzel-Seifert, K., Bürckstümmer, T., Pertz, H. H., Schunack, W., Dove, S., Buschauer, A., Elz, S., Multiple Differences in Agonist and Antagonist Pharmacology between Human and Guinea Pig Histamine H1-Receptor. J. Pharmacol. Exp. Ther. 2003, 305, 1104-1115.
(24) Preuss, H., Species-selective Interactions of Histamine H2 Receptors with Guanidine-type Agonists: Molecular Modelling, Site-directed Mutagenesis and Pharmacological Analysis.
Doctoral thesis, University of Regensburg, Germany 2007.
http://www.opus-bayern.de/uni-regensburg/frontdoor.php?source_opus=843&la=de.
(25) Jongejan, A., Lim, H. D., Smits, R. A., de Esch, I. J. P., Haaksma, E., Leurs, R., Delineation of Agonist Binding to the Human Histamine H4 Receptor Using Mutational Analysis, Homology Modeling, and ab Initio Calculations. J. Chem. Inf. Model. 2008, 48, 1455-1463.
(26) Schneider, E., Personal communication, Department of Pharmacology and Toxicology, University of Regensburg: Regensburg (Germany), 2008.
(27) Schnell, D., Personal communication, Department of Pharmacology and Toxicology, University of Regensburg: Regensburg (Germany), 2008.
(28) Xie, S.-X., Schalkhausser, F., Ye, Q.-Z., Seifert, R., Buschauer, A., Effects of Impromidine- and Arpromidine-Derived Guanidines on Recombinant Human and Guinea Pig Histamine H1
and H2 Receptors. Arch. Pharm. (Weinheim). 2007, 340, 9-16.
(29) Kraus, A., Highly Potent, Selective Acylguanidine-Type Histamine H2 Receptor Agonists:
Synthesis and Structure-Activity Relationships. Doctoral thesis, University of Regensburg, Germany 2007.
http://www.opus-bayern.de/uni-regensburg/frontdoor.php?source_opus=904&la=de.
(30) Krause, M., Rouleau, A., Stark, H., Luger, P., Lipp, R., Garbarg, M., Schwart, J. C., Schunack, W., Synthesis, X-ray crystallography, and pharmacokinetics of novel azomethine prodrugs of (R)-α-methylhistamine: highly potent and selective histamine H3 receptor agonists. J. Med.
Chem. 1995, 38, 4070-4079.
(31) Lin, J. S., Brain structures and mechanisms involved in the control of cortical activation and wakefulness, with emphasis on the posterior hypothalamus and histaminergic neurons. Sleep Med. Rev. 2000, 4, 471-503.
(32) Cannon, K. E., Nalwalk, J. W., Stadel, R., Ge, P., Lawson, D., Silos-Santiago, I., Hough, L. B., Activation of spinal histamine H3 receptors inhibits mechanical nociception. Eur. J. Pharmacol.
2003, 470, 139-147.
(33) Levi, R., Smith, N. C., Histamine H3-receptors: a new frontier in myocardial ischemia. J.
Pharmacol. Exp. Ther. 2000, 292, 825-830.
(34) Rouleau, A., Garbarg, M., Ligneau, X., Mantion, C., Lavie, P., Advenier, C., Lecomte, J. M., Krause, M., Stark, H., Schunack, W., Schwartz, J. C., Bioavailability, antinociceptive and antiinflammatory properties of BP 2-94, a histamine H3 receptor agonist prodrug. J.
Pharmacol. Exp. Ther. 1997, 281, 1085-1094.
(35) McLeod, R. L., Aslanian, R., del Prado, M., Duffy, R., Egan, R. W., Kreutner, W., McQuade, R., Hey, J. A., Sch 50971, an orally active histamine H3 receptor agonist, inhibits central neurogenic vascular inflammation and produces sedation in the guinea pig. J. Pharmacol.
Exp. Ther. 1998, 287, 43-50.
(36) Chen, B. C., Skoumbourdis, A. P., Sundeen, J. E., Rovnyak, G. C., Traeger, S. C., Efficient Molar-Scale Synthesis of 1-Methyl-5-acylimidazole Triflic Acid Salts. Org. Process Res. Dev.
2000, 4, 613-614.
(37) Geerts, J.-P., Motte, G., Differding, E., Henichart, J.-P. Preparation of substituted 4-(1,2,3,4-tetrahydro-1-naphthalenyl)-1H-imidazoles and 4-(2,3-dihydro-1H-inden-1-yl)-1H-imidazoles and their formulations as antiischemics and antihypertensives. EP 717037, 1996, Chem.
Abstr. 125:114632.
(38) Brana, M. F., Guisado, C., Sanz, F., Synthesis of new 4,5,6,7-tetrahydro-3H-imidazo[4,5-c]pyridine derivatives. 2003, 40, 917-923.
Structure-activity relationships of NG-acylated imidazolylalkylguanidines 163
(39) Nguyen, D. N., Stump, C. A., Walsh, E. S., Fernandes, C., Davide, J. P., Ellis-Hutchings, M., Robinson, R. G., Williams, T. M., Lobell, R. B., Huber, H. E., Buser, C. A., Potent inhibitors of farnesyltransferase and geranylgeranyltransferase-I. 2002, 12, 1269-1273.
(40) Bermudez, J., King, F. D., Sanger, G. J., Indazole and indoline as aromatic bioisosteres in the imidazole class of serotonin 5-HT3 receptor antagonists. Bioorg. Med. Chem. Lett. 1992, 2, 1509-1512.
(41) Rudolf, K., Hurnaus, R., Stenkamp, D., Mueller, S., Krist, B. Preparation and use of substituted imidazoles as selective histamine H3 receptor agonists. WO 2003040106, 2003, Chem. Abstr. 138:368893.
(42) Stark, H., Purand, K., Hüls, A., Ligneau, X., Garbarg, M., Schwartz, J.-C., Schunack, W., [125I]Iodoproxyfan and Related Compounds: A Reversible Radioligand and Novel Classes of Antagonists with High Affinity and Selectivity for the Histamine H3 Receptor. J. Med. Chem.
1996, 39, 1220-1226.
(43) Menghin, S., Pertz, H. H., Kramer, K., Seifert, R., Schunack, W., Elz, S., Nα-Imidazolylalkyl and Pyridylalkyl Derivatives of Histaprodifen: Synthesis and in Vitro Evaluation of Highly Potent Histamine H1-Receptor Agonists. J. Med. Chem. 2003, 46, 5458-5470.
(44) Wolin, R., Connolly, M., Afonso, A., Hey, J. A., She, H., Rivelli, M. A., Willams, S. M., West, R.
E., Novel H3 receptor antagonists. Sulfonamide homologs of histamine. Bioorg. Med. Chem.
Lett. 1998, 8, 2157-2162.
(45) Graßmann, S., Apelt, J., Sippl, W., Ligneau, X., Pertz, H. H., Zhao, Y. H., Arrang, J.-M., Ganellin, C. R., Schwartz, J.-C., Schunack, W., Stark, H., Imidazole Derivatives as a Novel Class of Hybrid Compounds with Inhibitory Histamine N-Methyltransferase Potencies and Histamine hH3 Receptor Affinities. Bioorg. Med. Chem. 2003, 11, 2163-2174.
(46) Walseth, T. F., Johnson, R. A., The enzymatic preparation of [α-32P] nucleoside triphosphates, cyclic [32P] AMP, and cyclic [32P] GMP. Biochim. Biophys. Acta 1979, 562, 11-31.