R-isoproterenol

The (R)-amino ketone is hydrogenated enantioselectively by a neutral complex [ (S)-(i )-BPPFOH RhCl]2 to give the (R,R)-isoproterenol analogue, a compound which has been shown to possess very potent /9-adrenoreceptor agonistic activity... 

Attempt to shorten APD with drugs (e.g.r isoproterenol) or electrical pacing... 

Its presence in the absolute R stereochemistry at the benzylic position is essential for potent 6-adrenoreceptor activity. In all known instances, these are the levorotatory (-)-Isomers (22, 25, 30, 32, 63, 141). Generally, the S (+)-enantlo-mers have only weak 6-adrenerglc receptor activity. Interestingly, a-adrenerglc receptor agonist activity is described for R-isoproterenol whereas the S-isomer is an antagonist (51, 142, 143). 

The optimal cross-linker is also dependent upon the template and solvent. When imprinting proteins, for example, a water-soluble cross-linker is needed like the water-soluble cross-linker A,A -methylene diacrylamide (methyleneb-isacrylamide). Divinylbenzene (DVB) is also a popular cross-linker and has been shown to be efficient for certain imprinting systems. An example of this is in the second imprinting protocol in this chapter, where DVB is used as a cross-linker for imprinting the chiral template (R) -isoproterenol. 

In the second example, we will imprint a chiral template, (R)-isoproterenol (as depicted in Fig. 9), which is another common asthma medication [41]. The synthesis of materials that can discriminate between enantiomers [24] demonstrates the vast potential of the imprinting technique. Because the chemical and physical properties of enantiomers are identical in anonchiral environment, the observation of enantios-electivity in MIPs can only be attributed to the three-dimensional arrangement of the functional monomers around the template molecule. Chiral selectivity in MIPs can be readily observed in batch-mode binding and competition studies [31] similar to the one described in the theophylline MIP protocol. In this case, however, we will present a procedure for evaluating the MIP as a HPFC packing material in order to... 

Optically active halohydrins or styrene oxide derivatives obtained by the reduction of a-halo ketones followed by treatment with base have been widely used as key intermediates in the synthesis of many chiral drugs containing the p-amino alcohol moiety. Examples of such drugs include (R)-denopamine (13) [46a], (R)-isoproterenol (14) [46b], d-solatol (15) [47], (R)-fluoro(nor)epinephrine (16) [48], (R)-salmeterol (17) [49], and (R,R)-formoterol (18) [50] (Scheme 11.4). Most OABs were effective for the reduction of 2-bromo- or 2-chloroacetophenone derivatives (22), providing the corresponding halohydrins with high enantioselectivities (Table 11.4). 

Fig. 2. Tic densitometer scans showing the resolution of isoproterenol on a hpflc siUca-gel plate obtained using a mobile phase consisting of 6.8 mM (1 R)-(—)-ammonium-10-camphorsu1fonic acid in 75 25 (v/v) methylene chioride methano1. (a) 254 nm, (b) 275 m, (c) 300 nm.

Division of the receptors in the adrenergic nervous system into two classes (a and P) was proposed in 1948 (39) when a difference in the rank order of potency of epinephrine (1, R = CH ), norephinephrine (1, R = H), and isoproterenol [7683-59-2], C H yNO, (1, R = CH(CH3)2) was noted to depend on the organ examined. Eurther subdivision into groups P2 proposed in 1967 (40). Both types of P-adrenoceptors are found throughout the... 

Pesoia, G. R., Walle, T., Stereoselective sulfate conjugation of isoproterenol in humans comparison of hepatic, intestinal and platelet activity, Chirality 1993, 5, 602-609. 

Most interesting in this light are our initial experiments on mouse bladder showing the absolute dependence of [i adrenergic relaxation in the bladder to the presence of PLB. Isoproterenol or forskolin activation of the A -kinase pathway led to complete relaxation of bladder from wild type mice, with little or no response in the PLB knockout bladder (K. Nobe R. J. Paul, unpublished observations). On the other hand, relaxation via G -kinase pathway activation was identical in the PLB knockout and wild-type bladder. PLB modulation of SR appears to be the dominant pathway for A-kinase mediated relaxation in mouse bladder in contrast to its lesser role in this pathway for the vascular tissues studied. 

Ingram, R.H., Wellman, J.J., McFadden, E.R., Jr. and Mead, J. (1977). Relative contributions of large and small airways to flow limitation in normal subjects before and after atropine and isoproterenol. J. Clin. Invest. 59 696-703. 

R.G. Johnson, S.E. Carty, S. Hayflick, A. Scarpa, Mechanisms of accumulation of tyramine, metaraminol, and isoproterenol in isolated chromaffin granules and ghosts, Biochem. Phamacol. 31 (1982) 815-823. 

Bi isoproterenol, dobutamine Atenolol, practolol Excitatory jX+ conductance, r cAMP... 

Sethi, R., and Dhalla, N.S. 1995. Inotropic responses to isoproterenol in congestive heart failure subsequent to myocardial infarction in rats. J. Card. Fail. 1 391-399. 

Fig. 4.2 (a) Aortic output during reperfusion after 25 min global ischemia of hearts preconditioned with different concentrations of isoproterenol, (b) Aortic output during reperfusion after 25 min global ischemia of hearts preconditioned with different concentrations of forskolin (l(r6-l(r 8 M). 

Harrison, W. H., Gray, R. M., and Solomon, L. M., Incorporation of L-DOPA, L-a-methylDOPA and DL-isoproterenol into guinea pig hair, Acta Dermatovener (Stockholm), 54, 249,1974. 

Fig. 22.1 Cardiovascular effects of noradrenaline (norepinephrine), adrenaline (epinephrine) and isoprenaline (isoproterenol) pulse rate/min, blood pressure in mmHg (dotted line is mean pressure), peripheral resistance in arbitrary units.The differences are due to the differential a and p agonist selectivities of these agents (see text). (By permission,after GinsburgJ,Cobbold A F I960 ln Vane J R et al (eds) Adrenergic mechanism. Churchill, London)...

Altiere, R.J. and Diamond, L. (1984). Comparison of vasoactive intestinal peptide and isoproterenol relaxant effects in isolated cat airways. J. Appl. Physiol. 56, 986-992. 

Cerrina, J., Ladurie, M., Le, R., Labat, C., Raffestin, B., Bayol, A. and Brink, C. (1986). Comparison of human bronchial muscle responses to histamine in vivo with histamine and isoproterenol agonists in vitro. Am. Rev. Respir. Dis. 137, 57-61. 

R.R. Padua, and E. Kardami, Increased basic fibroblast growth factor (bFGF) accumulation and distinct patterns of localization in isoproterenol-induced cardiomyocyte injury, Growth Factors 8, 291-306 (1993). 

S.K. Moule and R.M. Denton, The activation of p38 MAPK by the j8-adrenergic agonist isoproterenol in rat epididymal fat cells, FEBS Lett., 1998, 439, 287-290. 

Solich, R, Polydorou, C. K., Koupparis, M. A., and Efstathion, C. E. Automated flow-injection spectrophotometric determination of catecholamines (epinephrine and isoproterenol) in pharmaceutical formulations based on ferrous complex formation. J. Pharm. Biomed. Anal. 22(5) 781-789,2000. 

Figure 15.7. Effects of bufuralol-related soft drugs (19)on isoproterenol-induced tachycardia (i.v. bolus of 3.8 jLtmol/kg vebicle 10%DMSO in 30%hydroxypropyl j3-cyclodextrin) and resting heart rate (i.v. infusion, pmol/kg/min, R = Et 4 pmol/kg/min, esmoiol 20 pmol/kg/min vehicle0.9%NaCl) in rats. Data represent the means of at least three animals error hars were omitted for better visibility.

Jayalakshmi R, Niranjali Devaraj S. Cardioprotective effect of tincture of Crataegus on isoproterenol-induced myocardial infarction in rats. J Pharm Pharmacol. 2004 56 921-6. 

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