Dopamine derivatives

Kobayashi, N. et al., Formation and occurrence of dopamine-derived betacyanins. Phytochemistry, 56, 429, 2001. 

Dobutamine (76), on the other hand, is a dopamine derivative which does not act centrally, but is of interest because of its coronary vasodilator properties. Such drugs are potentially of value in treatment of angina pectoralis. Further, it is now undergoing extensive clinical trials as an inotropic agent for use in heart failure. Its synthesis is effected by Raney nickel catalyzed reduction of methyl p-methoxyvinylphenylketone (75) to its dihydro analog followed by reductive alkylation with p-(3,4-dimethoxyphenyl)ethylamine. The ether groups are cleaved with HBr to complete the synthesis of... 

A recently proposed explanation of PD involves the formation of adducts between dopamine and the products of the peroxidation of arachidonic acid and docosahexanoic acid (Liu et ah, 2008b). At least two compounds, hexanoyl-dopamine and propanoyl-dopamine, derived... 

M. Naoi, W. Maruyama, G. M. Nagy (2004). Dopamine-derived salsolinol derivatives as endogenous monoamine oxidase inhibitors occurrence, metabolism and function in human brains. Neurvtoxicology 25 193-204. 

As a first step toward a dopamine-jS-hydroxylase mimic, basket-shaped receptor 17 was functionalized with two sets of bis-[2-(3,5-dimethyl-l-pyra-zolyl)ethyl]amine ligands to give compound 35 (see Scheme 5). Reaction of 35 with Cu(C104,)2-6H20 yielded complex 36 which was fully characterized [39], Ligand system 35 binds dopamine derivative 37 and phloroglucinol (1,3,5-trihydroxybenzene) with association constants of = 60 and 3500 respectively. The affinity of the Cu(I) analogon of 36 for 37 was very similar to that of 36 itself and amounted to Ka = 60 M L Resorcinol is bound in the cavity of the Cu(I) complex with a Xj-value of 2(XX) M". ... 

A series of sulfur-containing dopamine-derived metabolites has been isolated from tunicates, predominantly belonging to the genus Lissoclinum. 

This [123I]iododopamine derivative 247 has been synthesized394 (equation 185) from the dopamine derivative 248.247 is used for animal studies currently. 

The photochemical Balz-Schiemann reaction has been used for the preparation of interesting fluoroarenc pharmaceutical agents, such as ring-fluorinated tyraminc and dopamine derivatives (Table 9. entries 1-3), and 2-, 5-, and 6-fluoronorepinephrine precursors (entries 4 and 5), from the corresponding nitroarenes. 

Although different nanomaterials such as nanoparticles, nanowires and nanotubes are used for the construction of biosensor, this chapter is mainly devoted to the use of AuNPs for the construction of electrochemical biosensor and their analytical performances. Further, in this chapter we restrict ourselves in the electrochemical sensing of glucose, ascorbic acid, uric acid and dopamine derivatives using the AuNPs modified electrodes. 

Fig. 6.1. Separation of some dopamine derived isoquinoline alkaloids...

Fig. 6.2. Separation of some dopamine derived isoquinoline alkaloids Column Vydac TP 401 SCX 10 pm (250x3.2 nrn ID), mobile phase 0.2 M NH.H.P0., flow rate 0.5 ml/min, column temperature 51°C, detection UV 280 nm. Peaks 1, dopamine-, 2, salsolinol 3, tetrahydropapaveroline 4, 2,3,10,11-tetrahydroxyberbine 5, 3 -0-methyltetrahydropapaveroline 6, 2,3,9,10-tetrahydroxyberbine 7, 7-0-methyltetrahydropapaveroline 8, 4 -0-methyl-tetrahydropapaveroline 9, 6-0-methyltetrahydropapaveroline 10, 2-0-methyltetrahydroxyberbine 11, 11-0-methyltetrahydroxyberbine 12, 10-0-methyltetrahydroxyberbine 13, 3-0-methyl-tetrahydroxyberbine. (Fig. 6.1 and 6.2 were reproduced with permission from ref. 26, by courtesy of Marcel Dekker, Inc.).

The generality of this new type of shape-activity correlation is demonstrated for five receptor/substrate systems trypsin/arylammonium inhibitors the D2-dop-amine receptor/dopamine derivative agonists trypsin/organophosphate inhibitors acetylcholinesterase/organophosphates and butyrylcholinesterase/organo-phosphates. The correlations were obtained both for active-site induced chiral conformers and for inherently chiral inhibitors. Interestingly, for some of these cases the correlation of activity with structure is hidden when classical parameters, such as chain length, are taken, but is revealed with this shape descriptor. 

Another type of fluorinated amino acid analogs are the -fluoromethylene derivatives of the acids [3]. For example, fluoromethylene dopa is metabolized to the corresponding dopamine derivative, which is a powerful inhibitor of monoamine oxidase and thus of interest for treatment of Parkinson s disease (Scheme 4.37). 

Other F-labeled tracers, for example different fluorinated dopamine derivatives, enable, e.g., very differentiated diagnosis of Parkinson s disease [86]. Fluorine-18-derivatized diagnostics have also been used to trace the metabolic pathway of drugs through the body in clinical tests. The radiation dose to which the test person is subjected is in the same range as, e. g., that used for a stomach X-ray examination. Examples of F-labeled radiopharmaceuticals and their target sites and applications are illustrated in Scheme 4.39. 

Four type of coupling reactions were carried out, which are shown in Fig. (11) and Fig. (13). (The cyclic skeletons were numbered according to the biogenetic numbering [40]). For the description of the stereogenic elements of the products the following system was used configuration of the new center of chirality (C-3 in tryptamine and oxotryptamine derivatives, C-l in dopamine and histamine derivatives) R or S type of conformation around C-l4 (in dopamine derivatives C-ll, in histamine derivatives C-10) 11,. .. 33, (see Fig. (14)) conformation of the... 

Removal of the benzylic OH, i.e., to give a dopamine derivative markedly reduces 6-adrenerglc agonist activity (144, 145) to a level comparable to that of the less potent phenylethanolamlne enantiomer, an observation that has been rationalized at the receptor level (146). Replacement of the benzylic OH with a carbonyl group (123) results in a marked decrease in effectiveness in various tests for adrenoreceptor activity ( , 147). In the... 

Most of the effects of the combined use of levodopa and beta blockers seem to be favourable, although additive hypotension can be a problem. Dopamine derived from levodopa stimulates beta-receptors in the heart, which can cause arrhythmias. These receptors are blocked by propranolol and other beta blockers. An enhancement of the effects of levodopa and a reduction in tremor has been described in 23 out of 25 patients taking propranolol, but not in 9 patients taking oxprenolol, or in another placebo-controlled study in 18 patients taking propranolol. Early evidence showed that growth hormone levels were substantially raised by propranolol or practolol [now withdrawn due to fatal reactions] in conjunction with levodopa, but no clinical relevance for this has been demonstrated. 

The electrochemical and spectral studies of the reaction between phenothiazine derivatives and acetylcholine, serotonin, and dopamine derivatives confirmed that charge transfer reactions occur. 

The incentive to utilize for the first time tt-tt complexation for selectively removing overdosed and toxic lipophilic aromatic compounds from blood originated from the work of Dust on binding dopamine derivatives to trinitrobenzene [47]. In that and other subsequent publications [42,48-50], spectroscopic methods are described for quantitative determination of complexation as well as how to calculate binding constants and activation energies. 

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