Synthesis of some novel organic nitrates and comparative in vitro study of their vasodilator profile

Journal of Medicinal Chemistry

Volumn 52, Issue 13, 2009, Pages 4020-4025

  Chegaev, Konstantin ^a   Lazzarato, Loretta ^a   Marcarino, Paolo ^a   Di Stilo, Antonella ^a   Fruttero, Roberta ^a   Vanthuyne, Nicolas ^b   Roussel, Christian ^b   Gasco, Alberto ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b AIX MARSEILLE UNIVERSITÉ   (France)

Author keywords

[No Author keywords available]

Indexed keywords

1 PHENYLPROPANE 1,2,3 TRIYL TRINITRATE; 1H 1,2,4 OXADIAZOLO[4,3 A]QUINOXALIN 1 ONE; 3 PHENYLPROPANE 1,2 DIYL DINITRATE; 3 PHENYLPROPYL NITRATE; 4 PHENYLBUTANE 1,2 DIYL DINITRATE; 4 PHENYLBUTYL NITRATE; ALDEHYDE DEHYDROGENASE INHIBITOR; ALDEHYDE DEHYDROGENASE ISOENZYME 2; BENOMYL[METHYL 1 (BUTYLCARBAMOYL) 2 BENZIMIDAZOLE CARBAMATE]; CHLORAL HYDRATE; ERYTHRO 4 PHENYLBUTANE 1,2,3 TRIYL TRINITRATE; GLYCERYL TRINITRATE; ORGANIC NITRATE; PHENYLEPHRINE; THREO 4 PHENYLBUTANE 1,2,3 TRIYL TRINITRATE; UNCLASSIFIED DRUG;

ANIMAL EXPERIMENT; ANIMAL TISSUE; AORTA STRIP; ARTICLE; CHIRAL CHROMATOGRAPHY; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CROSS TOLERANCE; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; IN VITRO STUDY; MALE; NONHUMAN; RACEMIC MIXTURE; RAT; THORACIC AORTA; VASODILATATION;

ALDEHYDE DEHYDROGENASE; ANIMALS; AORTA; DOSE-RESPONSE RELATIONSHIP, DRUG; MITOCHONDRIAL PROTEINS; NITRATES; NITROGLYCERIN; PHENYLEPHRINE; RATS; STRUCTURE-ACTIVITY RELATIONSHIP; VASODILATION; VASODILATOR AGENTS;

EID: 67649989734     PISSN: 00222623     EISSN: None     Source Type: Journal    
DOI: 10.1021/jm9002236     Document Type: Article

References (26)

1. Ahlner, J.; Andersson, R. G. G.; Torfgard, K.; Axelsson, K. L. Organic nitrate esters: clinical use and mechanisms of action. Pharmacol. Rev. 1991, 43, 351-423.
2. Glasser, S. P. Clinical mechanisms of nitrate action. Am. J. Cardiol. 1998, 81 (1A), 49A-53A.
3. (a) Chen, Z.; Zhang, J.; Stamler, J. S. Identification of the enzymatic mechanism of nitroglycerin bioactivation. Proc. Natl. Acad. Sci. U.S.A. 2002, 95, 10-15.
4. (b) Harrison, R. Organic nitrates and nitrites. In Nitric Oxide Donors; Wang, P. G., Cai, T. B., Taniguchi, N., Eds.; Wiley-VCH: Weinheim, 2005, pp 33-54.
5. (a) Abrams, J.; Elkayam, U.; Thadani, U.; Fung, H.-L. Tolerance: an historical overview. Am. J. Cardiol. 1998, 81 (1A), 3A-14A.
6. (b) Daiber, A.; Wenzel, P.; Oelze, M.; Münzel, T. New insights into bioactivation of organic nitrates, nitrate tolerance and cross-tolerance. Clin. Res. Cardiol. 2008, 97, 12-20.
7. (c) Mayer, B.; Beretta, M. The enigma of nitroglycerin bioactivation: news, views and troubles. Br. J. Pharmacol. 2008, 155, 170-184.
8. Marsh, N.; Marsh, A. A. A short history of nitroglycerine and nitric oxide in pharmacology and physiology. Clin. Exp. Pharmacol. Physiol. 2000, 27, 313-319.
9. Chegaev, K.; Lazzarato, L.; Tron, G.-C.; Marabello, D.; Di Stilo, A.; Cena, C.; Fruttero, R.; Gasco, A.; Vanthuyne, N.; Roussel, C. Synthesis, chiral HPLC resolution and configuration assignment of 1-phenylglyceryl trinitrate stereomers. Chirality 2006, 18, 430-436.
10. Dunstan, I.; Griffiths, J. V.; Harvey, S. A. Characterisation of the isomeric glycerol dinitrates. J. Chem. Soc. 1965, 131, 1319-1324.
11. Morris, L. J. A new method of cis-hydroxylation of olefins. Chem. Ind. 1958, 1291.
12. Axelsson, K. L.; Andersson, C.; Ahlner, J.; Magnusson, B.; Wikberg, J. E. S. Comparative in vitro study of a series of organic nitroesters: unique biphasic concentration-effect curves for glyceryl trinitrate in isolated bovine arterial smooth muscle and lack of stereoselectivity for some glyceryl trinitrate analogues. J. Cardiovasc. Pharmacol. 1992, 19, 953-957.
13. Kleschyov, A. L.; Oelze, M.; Daiber, A.; Huang, Y.; Mollnau, H.; Schulz, E.; Sydow, K.; Fichtlscherer, B.; Mülsch, A.; Münzel, T. Does nitric oxide mediates the vasodilator activity of nitroglycerin? Circ. Res. 2003, 93, 104-112.
14. -/- mice. Br. J. Pharmacol. 2007, 150, 526-533.
15. (a) Garthwaite, J.; Southam, E.; Boulton, C. L.; Nielsen, E. B.; Schmidt, K.; Mayer, B. Potent and selective inhibition of nitric oxide-sensitive guanylyl cyclase by 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one. Mol. Pharmacol. 1995, 48, 184-186.
16. (b) Schrammel, A.; Behrends, S.; Schmidt, K.; Koesling, D.; Mayer, B. Characterization of 1H-[1,2,4]oxadiazolo[4,3-a]quinoxalin-1-one as a heme-site inhibitor of nitric oxide-sensitive guanylyl cyclase. Mol. Pharmacol. 1996, 50, 1-5.
17. (c) Brunner, F.; Schmidt, K.; Nielsen, E. B.; Mayer, B. Novel guanylyl cyclase inhibitor potently inhibits cyclic GMP accumulation in endothelial cells and relaxation of bovine pulmonary artery. J. Pharmacol. Exp. Ther. 1996, 277, 48-53.
18. Chen, Z.; Stamler, J. S. Bioactivation of nitroglycerin by the mitochondrial aldehyde dehydrogenase. Trends Cardiovasc. Med. 2006, 16, 259-265.
19. Sydow, K.; Daiber, A.; Oelze, M.; Chen, Z.; August, M.; Wendt, M.; Ullrich, V.; Mülsch, A.; Schulz, E.; Keaney, J. F., Jr.; Stamler, J. S.; Münzel, T. Central role of mitochondrial aldehyde dehydrogenase and reactive oxygen species in nitroglycerin tolerance and cross-tolerance. J. Clin. Invest. 2004, 113, 482-489.
20. Collonge, J.; Poilane, G. Utilisation du chloro-4 butène-2 ol-1 en synthèse organique. Action sur les compose s organomag ne sien. Bull. Soc. Chim. Fr. 1955, 953-956.
21. McKillop, A.; Ford, M. E. Mercury-assisted solvolyses of alkyl halides. Simple procedures for the preparation of nitrate esters, acetate esters, alcohols and ethers. Tetrahedron 1974, 30, 2467-2475.
22. Bron, J.; Sterk, G. J.; van der Werf, J. F.; Timmerman H. Pharmaceutical composition having relaxing activity which contains a nitrate ester as active substance. European Patent EP0359335 (A2), March 21, 1990.
23. Organ, M. G.; Cooper, J. T.; Rogers, L. R.; Soleymanzadeh, F.; Paul, T. Sakurai addition and ring annulation of allylsilanes with alpha, beta-unsaturated esters. Experimental results and ab initio theoretical predictions examining allylsilane reactivity. J. Org. Chem. 2000, 65, 7959-7970.
24. Fernandes, R. A. A short synthesis of (+)-(S)-kurasoin B. Tetrahedron: Asymmetry 2008, 19, 15-18.
25. Roussel, C.; Vanthuyne, N.; Serradeil-Albalat, M.; Vallejos, J.-C. True or apparent reversal of elution order during chiral high-performance liquid chromatography monitored by a polarimetric detector under different mobile phase conditions. J. Chromatogr. A 2003, 995, 79-85.
26. Keith, R. A.; Burkman, A. M.; Sokoloski, T. D.; Ferter, R. H. Vascular tolerance to nitroglycerin and cyclic GMP generation in rat aortic smooth muscle. J. Pharmacol. Exp. Ther. 1989, 221, 525-531.