A structure-activity relationship study of compounds with antihistamine activity

Biomedical Chromatography

Volumn 20, Issue 10, 2006, Pages 1004-1016

  Brzezińska, Elzbieta ^a   Kośka, Grazyna ^a  

^a MEDICAL UNIVERSITY OF LODZ   (Poland)

Author keywords

Benzothiazoles; Discriminant analysis; Structure activity relationship (SAR); Thiazoles; TLC

Indexed keywords

AMINO ACIDS; DISCRIMINANT ANALYSIS; PLATES (STRUCTURAL COMPONENTS); SILICA GEL;

ACTIVITY RELATIONSHIP ANALYSIS; ASPARTIC ACIDS; BENZOTHIAZOLES; CHROMATOGRAPHIC DATA; HISTAMINES; SILANIZED; STRUCTURE-ACTIVITY RELATIONSHIP; STRUCTURE-ACTIVITY RELATIONSHIPS; THIAZOLE; TLC;

PROPIONIC ACID;

2 (1 PIPERAZINYL 1H 1,4 DIAZEPIN 1 YL)BENZOTHIAZOLE; 2 (1 PIPERAZINYL)BENZOTHIAZOLE; 2 (2 BENZHYDRYLTHIAZOL 4 YL)ETHYLAMINE; 2 (2 BENZYL 4 THIAZOLYL)ETHYLAMINE; 2 (HEXAHYDRO 1H 1,4 DIAZEPIN 1 YL)BENZOTHIAZOLE; 2 (N,N',N' DIMETHYLALKYL 1,2 ETHANEDIAMINO)BENZOTHIAZOLE; 2 [1 (4 AMINOPIPERIDINYL)]BENZOTHIAZOLE; 2 [2 (PHENYLAMINO)THIAZOL 4 YL]ETHYLAMINE; 2 [2 PHENYL 4 THIAZOLYL]ETHYLAMINE; 2 [4 (1 ALKYL)PIPERIDINYL]BENZOTHIAZOLE; ANTIHISTAMINIC AGENT; ASPARTIC ACID; ASTEMIZOLE; BENZOTHIAZOLE DERIVATIVE; CETIRIZINE; CIMETIDINE; DIPHENHYDRAMINE; FAMOTIDINE; HISTAMINE H1 RECEPTOR; HISTAMINE H2 RECEPTOR; HISTAMINE H3 RECEPTOR; HISTAMINERGIC RECEPTOR AFFECTING AGENT; KETOTIFEN; LEVOCABASTINE; LORATADINE; PROMETHAZINE; PROPIONIC ACID; RANITIDINE; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; CHROMATOGRAPHY; DISCRIMINANT ANALYSIS; DRUG STRUCTURE; LIPOPHILICITY; PREDICTION; QUANTITATIVE ANALYSIS; RECEPTOR BLOCKING; STRUCTURE ACTIVITY RELATION;

EID: 33750717541     PISSN: 02693879     EISSN: 10990801     Source Type: Journal    
DOI: 10.1002/bmc.621     Document Type: Article

References (49)

1. Alves CN, Pinheiro JC, Camargo AJ, Ferreira MMC and da Silva ABF. A structure-activity relationship study of HEPT-analog compounds with anti-HIV activity. Journal of Molecular Structure (THEOCHEM) 2000; 530: 39.
2. Barnett A, Iorio LC, Kreutner W, Tozzi S, Ahn HS and Gulbenkian A. Evaluation of the CNS properties of SCH 29851, a potential non-sedating antihistamine. Agents and Actions 1984; 14: 590.
3. Bate-Smith EC and Westall RG. Chromatographicy behavior and chemical structure. I. Some naturally occuring phenolic substances. Biochimica Biophysica Acta 1950; 4: 427.
4. Bradshaw J, Brittain RT, Clitherow JW, Daly MJ, Jack D, Price BJ and Stables R. Ranitidine (AH 19065): a new potent, selective histamine H2-receptor antagonist [proceedings]. British Journal of Pharmacology 1979; 66: 464P.
5. Brimblecombe RW, Duncan WAM, Duraut GI, Emmett IC, Ganellin CR and Parsons ME. Cimetidine - a non-thiourea H2-receptor antagonist. Journal of Internal Medical Research 1975a; 3: 86.
6. Brimblecombe RW, Duncan WA, Durant GJ, Ganellin CR, Parsons ME and Black JW. Proceedings: The pharmacology of cimetidine, a new histamine H2-receptor antagonist. British Journal of Pharmacology 1975b; 53: 435.
7. 1-antihistamine activity. Part 1. Journal of Planar Chromatography 2003a; 16: 451.
8. 1-antihistamine activity. Part 2. Journal of Planar Chromatography 2003b; 17: 40.
9. 1-antihistamine activity. I. Journal of Chromatography A 2003a; 1007: 145.
10. 1-antihistamine activity. II. Journal of Chromatography A 2003b; 1007: 157.
11. Canonica GW, Pesce G, Ruffoni S, Buscaglia S, Boero F, Jing G, Rihoux JP and Ciprandi G. Cetirizine does not influence the immune response. Annals of Allergy 1992; 68: 251.
12. Casabán-Ros E, Antón-Fos GM, Gálvez J, Duart MJ and García-Doménech R. Search for New Antihistaminic Compounds by Molecular Connectivity. Quantitative Structure Activity Relationships 1999; 18: 3.
13. Chinn HI and Smith PK. Motion sickness. Pharmacology Review 1955; 7: 33.
14. Daly MJ, Humphray JM and Stables R. Inhibition of gastric acid secretion in the dog by the H2-receptor antagonists, ranitidine, cimetidine, and metiamide. Gut 1980; 21: 408.
15. Danysz A. Kompendium farmakologii i farmakoterapii. Wydawnictwo Volumed: Wroclaw, 1994.
16. De Esch IJ, Timmerman H, Menge WM and Nederkoorn PH. A qualitative model for the histamine H3 receptor explaining agonistic and antagonistic activity simultaneously. Archiv fur Pharmakologie (Weinheim). 2000; 333: 254.
17. De Vos C, Maleux MR, Baltes E and Gobert J. Inhibition of histamine and allergen skin wheal by cetirizine in four animal species. Annals of Allergy 1987; 59: 278.
18. Ebnöther A and Weber HP. Synthesis and absolute configuration of clemastine and its isomers. Helvetica Chimica Acta 1976; 59: 2462.
19. Gami-Yilinkou R, Nasal A and Kaliszan R. Application of chemometrically processed chromatographic data for pharmacologically relevant classification of antihistamine drugs. Journal of Chromatography 1993; 633: 57.
20. Grant SM, Goa KL, Fitton A and Sorkin EM. Ketotifen. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic use in asthma and allergic disorders. Drugs 1990; 40: 412.
21. Hill SJ, Ganellin CR, Timmerman H, Schwartz JC, Shankley NP, Young JM, Schunack W, Levi R and Haas HL. International Union of Pharmacology. XIII. Classification of histamine receptors. Pharmacology Review 1997; 49: 253.
22. Janssens MM. Introduction. Second-generation antihistamines. Clinical Reviews of Allergy 1993; 11: 1.
23. Janssens MM and Howarth PH. The antihistamines of the nineties. Clinical Reviews of Allergy 1993; 11: 111.
24. Johnson RA and Wichern DW. Applied Multivariate statistical Analysis. Prentice-Hall: Englewood Cliffs, NJ, 1992.
25. Juhlin L, de Vos C and Rihoux JP. Inhibiting effect of cetirizine on histamine-induced and 48/80-induced wheals and flares, experimental dermographism, and cold-induced urticaria. Journal of Allergy and Clinical Immunology 1987; 80: 599.
26. Kemmritz K. Antiallergica-Arzneimittel für die Selbstmedikation-kritischbewerten und kompetent auswerten. Springer: Berlin, 2003.
27. King RD, Muggleton SH, Srinivasan A and Sternberg MJ. Structure-activity relationships derived by machine learning: the use of atoms and their bond connectivities to predict mutagenicity by inductive logic programming. Proceedings of the National Academy of Science USA 1996; 93: 438.
28. Le Blaye I, Donatini B, Hall M and Krupp P. Acute ketotifen overdosage. A review of present clinical experience. Drug Safety 1992; 7: 387.
29. Loew DM, Grauwiler J, Griffith R, Taeschler M, Weidmann H and Zehnder K. Pharmacological, pharmacokinetic and toxicological research on mesoridazine (NC 123). Bollettino Chimico Farmaceutico 1967; 106: 332.
30. Marida KV, Kent JT and Bibbly JM. Multivariate Analysis. Academic Press: New York, 1979.
31. Marshall PB. Some chemical and physical properties associated with histamine antagonism. British Journal of Pharmacology and Chemotherapy 1955; 10: 270.
32. Martin U and Romer D. The pharmacological properties of a new, orally active antianaphylactic compound: ketotifen, a benzocycloheptathiophene. Arzneimittelforschung 1978; 28: 770.
33. Okada T. Discovery of structure activity relationships using the cascade model: The mutagenicity of aromatic nitro compouds. Journal of Computer-Aided Chemistry 2001; 2: 79.
34. Piwinski JJ, Wong JK, Green MJ, Ganguly AK, Billah MM, West RE Jr and Kreutner W. Dual antagonists of platelet activating factor and histamine. Identification of structural requirements for dual activity of N-Acyl-4-(5,6-dihydro-11H-benzo [5,6]cyclohepta-[1,2-b]pyridin-11-ylidene)piperidines. Journal of Medicinal Chemistry 1991; 34: 457.
35. Quiñones C, Caceres J, Stud M and Martinez A. Prediction of drug half-life values of antihistamines based on the CODES/Neural Network Model. Quantitative Structure Activity Relationships 2000; 19: 448.
36. 1-antihistaminic activity. Drug Development Research 1986; 8: 87.
37. Swiader M, Wielosz M and Czuczwar SJ. Influence of antazoline and ketotifen on the anticonvulsant activity of conventional antiepileptics against maximal electroshock in mice. European Neuropsychopharmacology 2004; 14: 307.
38. Takabatake T, Ohta H, Maekawa M, Yamamoto Y, Ishida Y, Hara H, Nakamura S, Ushiogi Y, Kawabata M, Hashimoto N et al. Pharmacokinetics of famotidine, a new H2-receptor antagonist, in relation to renal function. European Journal of Clinical Pharmacology 1985; 28: 327.
39. Tasaka K, Kamei C, Tsujimoto S, Yoshida T and Aoki I. Central effect of the potent long-acting H1-antihistamine levocabastine. Arzneimittelforschung 1990; 40: 1295.
40. Uzan A, Le Fur G and Malgouris C. Are antihistamines sedative via a blockade of brain H1 receptors? Journal of Pharmaceutical Pharmacology 1979; 31: 701.
41. Van der Brook MJ, Olson KJ, Richmond MT and Kuizenga MH. Pharmacology of a new anihistamine, 10-[β-(1-pyrrolidyne)ethyl]phenothiazine monohydrochloride (pyrrolazote). Journal of Pharmacology and Experimental Therapy 1948; 94: 197.
42. Van Wauwe J, Awouters F, Neimegeers CJ, Janssens F, Van Nueten JM and Janssen PA. In vivo pharmacology of astemizole, a new type of H1-antihistaminic compound. Archives of International Pharmacodynamic Therapy 1981; 251: 39.
43. Walczynski K, Timmerman H, Zuiderveld OP, Zhang MQ and Glinka R. Histamine H1 receptor ligands. Part I. Novel thiazol-4-ylethanamine derivatives: synthesis and in vitro pharmacology. Farmaco 1999a; 54: 533.
44. Walczynski K, Guryn R, Zuiderveld OP and Timmerman H. Nonimidazole histamine H3 ligands. Part I. Synthesis of 2-(1-piperazinyl)- and 2-(hexahydro-1H-1,4-diazepin-1-yl)benzothiazole derivatives as H3-antagonists with H1 blocking activities. Farmaco 1999b; 54: 684.
45. Walczynski K, Guryn R, Zuiderveld OP and Timmerman H. Nonimidazole histamine H3 ligands, Part 2: new 2-substituted benzothiazoles as histamine H3 antagonists. Archiv fur Pharmakologie (Weinheim) 1999c; 332: 389.
46. Walczynski K, Guryn R, Zuiderveld OP, Zhang MQ and Timmerman H. Histamine H1 receptor ligands: Part II. Synthesis and in vitro pharmacology of 2-[2-(phenylamino)thiazol-4-yl]ethanamine and 2-(2-benzhydrylthiazol-4-yl)ethanamine derivatives. Farmaco 2000; 55: 569.
47. Wauquier A and Niemegeers CJ. Effects of chlorpheniramine, pyrilamine and astemizole on intracranial self-stimulation in rats. European Journal of Pharmacology 1981; 72: 245
48. Windhorst AD, Timmerman H, Worthington EA, Bijloo GJ, Nederkoorn PH, Menge WM, Leurs R and Herscheid JD. Characterization of the binding site of the histamine H(3) receptor. 2. Synthesis, in vitro pharmacology, and QSAR of a series of monosubstituted benzyl analogues of thioperamide. Journal of Medical Chemistry 2000; 43: 1754.
49. Witiak DT, Muhi-Eldeen Z, Mahishi N, Sethi OP and Gerald MC. L(S)- and D(R)-3-amino-1-phenylpyrrolidines. Stereoselective antagonists for histamine and acetylcholine receptors in vitro. Journal of Medical Chemistry 1971; 4: 24.