Synthesis, QSAR and calcium channel modulator activity of new hexahydroquinoline derivatives containing nitroimidazole

Chemical Biology and Drug Design

Volumn 70, Issue 4, 2007, Pages 329-336

  Miri, Ramin ^a,b   Javidnia, Katayoun ^a,b   Mirkhani, Hossein ^a   Hemmateenejad, Bahram ^a,c   Sepeher, Zahra ^a   Zalpour, Masomeh ^a   Behzad, Taherh ^a   Khoshneviszadeh, Mehdi ^a   Edraki, Najmeh ^a   Mehdipour, Ahmad R ^a  

^a SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^b SHIRAZ UNIVERSITY OF MEDICAL SCIENCES   (Iran)

^c SHIRAZ UNIVERSITY   (Iran)

Author keywords

1,4 dihydropyridine; Antagonists agonists; Calcium channel; Hexahydroquinolin

Indexed keywords

1,4 DIHYDRO 2,6 DIMETHYL 5 NITRO 4 [2 (TRIFLUOROMETHYL)PHENYL] 3 PYRIDINECARBOXYLIC ACID METHYL ESTER; 2 CYCLOHEXYLETHYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; BENZYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; CALCIUM CHANNEL BLOCKING AGENT; CALCIUM CHANNEL STIMULATING AGENT; CYCLOHEXYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; CYCLOHEXYLMETHYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; CYCLOPENTYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; CYCLOPROPYLMETHYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; ETHYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; HEXAHYDROQUINOLINE DERIVATIVE; ISOBUTYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; ISOPROPYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; METHYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; NIFEDIPINE; NITROIMIDAZOLE DERIVATIVE; PHENETHYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; PHENYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; PROPYL 2 METHYL 4 (1 METHYL 5 NITRO 1H IMIDAZOL 2 YL) 5 OXO 1,4,5,6,7,8 HEXAHYDROQUINOLINE 3 CARBOXYLATE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL TISSUE; ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CONGESTIVE HEART FAILURE; CONTROLLED STUDY; DRUG SELECTIVITY; DRUG SYNTHESIS; GUINEA PIG; HANTZSCH REACTION; ILEUM; MALE; NONHUMAN; PRIORITY JOURNAL; QUANTITATIVE STRUCTURE ACTIVITY RELATION; RAT; SMOOTH MUSCLE;

ANIMALS; CALCIUM CHANNELS; DRUG DESIGN; GUINEA PIGS; HEART ATRIA; HUMANS; ILEUM; MALE; MOLECULAR STRUCTURE; MUSCLE, SMOOTH; NITROIMIDAZOLES; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; QUINOLINES;

CAVIA;

EID: 35148844314     PISSN: 17470277     EISSN: None     Source Type: Journal    
DOI: 10.1111/j.1747-0285.2007.00565.x     Document Type: Article

References (46)

1. 2+ channels. Ann Rev Cell Dev Biol 16: 521 555.
2. Psaty B.M., Heckbert S., Koepsell T., Siscovick D.S., raghunathan T.E., Weiss N.S., Rosendal F.R., Lemaitre R.N., Smith N.L., Wahl P.W., Wagner E.H., Furberg C.D. (1995) The risk of myocardial infarction associated with antihypertensive drug therapies. J Am Med Assoc 274: 620 625.
3. Navidpour L., Shafaroodi H., Miri R., Dehpour A.R., Shafiee A. (2004) Lipophilic 4-imidazoly-1,4-dihydropyridines: synthesis, calcium channel antagonist activity and protection against pentylenetetrazole-induced seizure. IL Farmaco 59: 261 269.
4. Mojarrad J.S., Miri R., Knaus E.E. (2004) Design and synthesis of methyl 2-methyl-7,7-dihalo-5-phenyl-2-azabicyclo[4.1.0]hept-3-ene-4-carboxylates with calcium channel antagonist activity. Bioorg Med Chem 12: 3215 3220.
5. Pourmorad F., Hadizadeh F., Shafiee A. (1997) Synthesis and calcium-channel antagonist activity of 4-imidazolyl-1,4-dihydropyridines. Pharm Sci 3: 165 168.
6. Triggle D.J. (1990) Ion channels. In: Clark C.R., Moos H., editors. Drug Discovery Technologies. Chichester: John Wiley & Sons p. 167.
7. Şafak C., Simsek R. (2006) Fused 1,4-dihydropyridines as potential calcium modulatory compounds. Mini Rev Med Chem 6: 747 755.
8. Triggle D.J. (2003) The 1,4-dihydropyridine nucleus: a pharmacophoric template: Part 1. Actions at ion channels. Mini Rev Med Chem 3: 215 223.
9. Ghodsi S., Alipour E., Amini M., Miri R., Tagi-Ganji M.K., Hosseini M., Mirkhani H., Shafiee A. (2006) The synthesis and characterization of new asymmetrical dihydropyridine derivatives containing a 2,4-dichloro-5-thiazolyl substituent. Phosphorus, sulfur, and silicon 181: 2435 2444.
10. Amini M., Golabchifar A., Dehpour A.R., Pirali Haedani M., Shafiee A. (2002) Synthesis and calcium channel antagonist activity of new 1,4-dihydropyridine derivatives containing dichloroimidazolyl substituents. Arzneim Forsch/Drug Res 52: 21 26.
11. Mikkelsen E.O., Nyborg N.C. (1986) Synthesis and calcium channel antagonist activity of new 1,4-dihydropyridine derivatives containing dichloroimidazolyl substituents. J Cardiovasc Pharmacol 8: 467 482.
12. Schramm M., Towart R., Kazda S., Thomas G., Franckowiak G. (1985) Calcium agonism, a new mechanism for positive inotropy. Hemodynamic effects and mode of action of BAY K 8644. Adv Myocardiol 6: 59 70.
13. Schramm M., Thomas G., Towart R., Franckowiak G. (1983) Novel dihydropyridines with positive inotropic action through activation of Ca2+ channels. Nature 303: 535 537.
14. Loutzenheiser R., Ruegg U.T., Hof A., Hof R.P. (1984) Studies on the mechanism of action of the vasoconstrictive dihydropyridine, CGP 28392. Eur J Pharmacol 105: 229 237.
15. Miri R., Javidnia K., Sarkarzadeh H., Hemmateenejad B. (2006) Synthesis, study of 3D structures, and pharmacological activities of lipophilic nitroimidazolyl-1,4-dihydropyridines as calcium channel antagonist. Bioorg Med Chem 14: 4842 4849.
16. Miri R., Javidnia K., Kebriaie-Zadeh A., Niknahad H., Shaygani N., Semnanian S., Shafiee A. (2003) Synthesis and evaluation of pharmacological activities of 3,4-dialkyl1,4-dihydro-2,6-dimethyl-4-nitroimidazole-3,5-pyridine dicarboxylates. Arch Pharm Pharm Med Chem 336: 422 428.
17. Miri R., Niknahad H., Vazin A., Azarpira A., Shafiee A. (2002) Synthesis and smooth muscle calcium channel antagonist effects of new derivatives of 1,4-dihydropyridine containing nitroimidzolyl substituent. DARU 10: 130 136.
18. Miri R., Niknahad H., Vesal G., Shafiee A. (2002) Synthesis and calcium channel antagonist activities of 3-nitrooxyalkyl, 5-alkyl 1,4-dihydro-2,6- dimethyl-4-(1-methyl-5-nitro-2-imidazolyl)-3,5-pyridinedicaboxylates. IL FARMACO 57: 123 128.
19. Shafiee A., Miri R., Dehpour A.R., Solimani F. (1996) Syntheses and calcium channel antagonist activity of nifedipine containing imidazolyl substitutent. Pharm Sci 2: 541 543.
20. Rose U., Dräger M. (1992) Synthesis, configuration, and calcium modulatory properties of enantiomerically pure 5-oxo-1,4,5,6,7,8- hexahydroquinoline-3-carboxylates. J Med Chem 35: 2238 2243.
21. Rose U. (1990) 5-Oxo-1,4-dihydroindenopyridines: calcium modulators with partial calcium agonistic activity. J Heterocycl Chem 27: 237 242.
22. Aydin F., Şafak C., Şimşek R., Erol K., Ulgen M., Linden A. (2006) Studies on condensed 1,4-dihydropyridine derivatives and their calcium modulatory activities. Pharmazie 61: 655 659.
23. Rose U. (1990) Vinylogous and coupled hexahydroquinolinones and dihydropyridines with calcium-modulating effects. Pharm Acta Helv 6: 178 185.
24. Rose U. (1991) Synthesis and pharmacological activities of calcium modulatory hexahydroquinolinones. Arzneim Forsch/Drug Res 41: 199 203.
25. Rose U. (1990) Hexahydroquinolinones with calcium-modulatory effects - synthesis and pharmacologic action. Arch Pharm Pharm Med Chem 323: 281 286.
26. Caballero J., Garriga M., Fernandez M. (2006) 2D Autocorrelation modeling of the negative inotropic activity of calcium entry blockers using Bayesian-regularized genetic neural networks. Bioorg Med Chem 14: 3330 3340.
27. Todeschini R., Consonni V. (2000) Handbook of Molecular Descriptors. Weinheim, Germany: Wiley-VCH.
28. Hansch C., Leo A., Taft R.W. (1991) A survey of hammett substituent constants and resonance and field parameters. Chem Rev 97: 165 195.
29. Hemmateenejad B., Miri R., Jafarpour M., Tabarzad M., Foroumadi A. (2006) Multiple linear regression and principal component analysis-based prediction of the anti-tuberculosis activity of some 2-aryl-1,3,4-thiazole derivatives. QSAR Comb Sci 25: 56 66.
30. Mager H. (1983) The problem of multicollinearity in Hansch-type quantitative structure-activity relationships (QSAR) and in chemical linear free energy relationships (LFER). Pharmazie 38: 120 128.
31. Hemmateenejad B., Miri R., Akhond M., Shamsipur M. (2002) QSAR study of the calcium channel antagonist activity of some recently synthesized dihydropyridine derivatives. An application of genetic algorithm for variable selection in MLR and PLS methods. Chemometr Intell Lab 64: 91 99.
32. Hemmateenejad B., Miri R., Akhond M., Shamsipur M. (2002) Quantitative structure-activity relationship study of recently synthesized 1,4-dihydropyridine calcium channel antagonists. Application of the Hansch analysis method. Arch Pharm Pharm Med Chem 335: 472 480.
33. Hemmateenejad B., Akhond M., Miri R., Shamsipur M. (2003) Genetic algorithm applied to the selection of factors in principal component-artificial neural networks: application to QSAR study of calcium channel antagonist activity of 1,4-dihydropyridines (nifedipine analogous). J Chem Inf Comput Sci 43: 1328 1334.
34. Hemmateenejad B., Safarpour M.A., Miri R., Taghavi F. (2004) Application of ab initio theory to QSAR study of 1,4-dihydropyridine-based calcium channel blockers using GA-MLR and PC-GA-ANN procedures. J Comput Chem 25: 1495 1503.
35. Hemmateenejad B., Miri R., Safarpour M.A., Khoshneviszadeh M., Edraki N. (2005) Conformational analysis of some new derivatives of 4-nitroimidazolyl-1,4- dihydropyridine-based calcium channel blockers. J Mol Struct: THEOCHEM 717: 139 152.
36. Hantzsch A. (1882) Justus Liebigs. Ann Chem 215: 1.
37. Clemens R.J., Hyatt H.A. (1985) Acetoacetylation with 2,2,6-trimethyl-4H-1,3-dioxin-4-one: a convenient alternative to diketene. J Org Chem 50: 2431 2435.
38. Meyer H., Bossert F., Wehinger E., Stoeple K., Vater W. (1981) Synthesis and comparative pharmacological studies of 1,4-dihydro-2,6-dimethyl-4-(3- nitrophenyl)pyridine-3,5-dicarboxylates with non-identical ester functions. Arzneim Forsch/Drug Res 31: 407 409.
39. Levy J.V. (1971) Isolated atrial preparation. In: Scwartz A., editor. Methods in Pharmacology. New York: Appleto-Century-Crofts, Meredith Crop p. 77.
40. Nakaya H., Hattori Y., Tohose N., Kanno M., Schemiedeberg N. (1986) Voltage-dependent effect of YC-170, a dihydropyridine calcium channel modulator, in cardiovascular tissues. Arch Pharmacol 333: 421 430.
41. Van Rossum J.M. (1963) Cumulative dose-response curves: II. Technique for the making of dose-response curves in isolated organs and the evaluation of drug parameters. Arch Int Pharmacodyn Ther 143: 299 330.
42. Perry W.L.M. (1970) Experiments with intestinal smooth muscle, 2nd edn. In: Blattner R., Classen H.G., Dehnert H., Doring H.J., editors. Pharmacological Experiments on Isolated Smooth Preparation. Edinburgh: Churchill Livingstone Co. p. 58.
43. Martin I., Colado I., Val V.D., Alfaro M. (1990) Dihydropyridines on guinea-pig ileum. Gen Pharmacol 21: 41 44.
44. Morel N., Hary P., Godfraind T. (1987) Histamine-operated calcium channels in intestinal smooth muscle of the guinea-pig. Eur J Pharmacol 135: 69 75.
45. Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G. et al. (1998) Gaussian 98, Revision A.7. Pittsburgh, PA: Gaussian, Inc.
46. Montgomery D.C., Peck E.A., Vining G.G. (2006) Introduction to Linear Regression Analysis. Weinheim, Germany: Wiley-VCH.