Aminoalkylating agents

Mannich reactions were first performed using commercially available Eschen-moser s salt as the aminoalkylating agent, and enolates derived from syn and anti... 

Table 5. Mannich Reaction of Enolates of 2-Propionyl-2-ethyl DiTOX Substrates Using Eschenmoser s Salt as Aminoalkylating Agent...

In this case the imine aminoalkylaling agent 100 is prepared from optically active galaclosylamino derivative. The success of the synthesis is determined by the good yield of the aminomethylation step in conjunction with the remarkable stereoselectivity of the reaction. 

Bis(aminoalkyl)bithiazoles are useful as DNA cleavage agents. Bleomycin contains a 2,4 -bithiazole moiety which plays an important role in the interaction with double stranded DNA during the cleavage reaction. The 2,2 -bis(aminomethyl)-4,4 -bithiazole (70) has been synthesised by the condensation of l,4-dibromobutane-2,3-dione with Boc-glycinethioamide... 

Imaginative use has been made of triazine and sulphatoethylsulphone reactive dye chemistry in the application of pretreatments to nylon [405]. The concept resembles that used to make cotton cellulose reactive before dyeing with aminoalkylated dyes, as discussed earlier (Schemes 10.67 and 10.68). In this case, nylon becomes the reactive partner by pretreatment with a reactive multifunctional crosslinking agent ... 

Add a quantity of Aminoethyl-8 in methanol to equal a 25-fold molar excess over the amount of sulfhydryl present (including the amount of DTT added). The solution in methanol should be made concentrated enough so only a small amount of methanol has to be added to the reaction solution (i.e., no more than 10 percent of the final volume). A second addition of modifying agent may be made after 1 hour to drive the reaction more completely toward total —SH aminoalkylation. 

More controlled and efficient fixation is possible when the reactant is applied as a pretreating agent [146]. If nylon given such a pretreatment is subsequently dyed with the conventional chlorotriazine dye Cl Reactive Red 3 (7.2), the substantivity and fixation of the latter are markedly lowered because the anionic XLC residues have reacted with N-terminal amino groups in the fibre. Treatment of the modified nylon with ammonia, however, restores some degree of dyeability. Opposite effects are observed if Cl Reactive Red 3 is reacted with ethylenediamine to form an aminoalkyl derivative (7.131). This nucleophilic dye exhibits a high degree of fixation only on the modified nylon that has been pretreated with XLC. 

Interest in Fixing Agent P (7.123) has been revived in the context of nucleophilic aminoalkyl dyes of the 7.129 and 7.131 types. Nylon pretreated with this symmetrical trifunctional reactant contains residual acryloyl sites that will undergo an addition reaction with nucleophilic dye molecules [145]. Although in theory each N-terminal amino group in the fibre can give rise to two acryloyl sites (Scheme 7.73), crosslinking between two N-... 

The analogous 4- (19, X = H2) and 5-phenyltetrahydro-l-benzazepines are less active than the 3-phenyl isomers [30]. The corresponding 4-phenyl-benzazepin-2-one (19, X = O) shows moderate antiarrhythmic activity [30] and is claimed to be useful for the treatment of neurogenic or carcinogenic auricular and ventricular fibrillation and as an antihistaminic or local anaesthetic agent [37]. Introduction of an aminoalkyl group, such as 2-piperidinyl-... 

Several drugs, in particular neuropharmacological agents, feature a car-boxylate group esterified to an aminoalkyl moiety. As a rule, such lipophilic compounds are good substrates for hydrolases, and their duration of action is influenced by their rate of hydrolysis (see also Sect. 7.3.4). A simple example is that of procaine (7.56), which is rapidly inactivated by hydrolysis [41] [76a], Various hydrolases catalyze the reaction, in particular plasma cholinesterase and cellular carboxylesterases. As often reported, atropine and scopolamine are rapidly hydrolyzed by plasma carboxylesterases in rabbits (with very large differences between individual animals), but are stable in human plasma [1] [75] [76a] [110]. 

In the case of the naphthalimide fluorescent brightening agents (98) the most important commercial derivatives are the 4-alkoxy and 4-acylamino (e.g. R is methoxy). Substituent R is usually an alkyl group or an aminoalkyl group capable of quaternization. Thus the most interesting of the series is 4-methoxy-Af-methylnaphthalimide, which is an excellent product suitable for application to a variety of synthetic fibres. 

By analogy to the Strecker-like synthesis of a-aminoalkylphosphonic acids (Section 10.10.1.1.1), alkyl phosphonites can be added to AMritylimines 66 in refluxing toluene to form aminoalkyl(alkyl)phosphinates 67 (Scheme 22, Table 10).[33] The addition of a catalytic amount of Lewis acid, such as BF3 OEt2, dramatically improves the chemical yield for this process. Moreover, alkyl phosphonites can be added to acylating agents, such as alkyl isocyanates 68, to form acyl(alkyl)phosphinates 69 (Scheme 22)J103l... 

Mitoxantrone (mitozantrone) (Figure 3.57) is a synthetic analogue of the anthracyclinones in which the non-aromatic ring and the aminosugar have both been replaced with aminoalkyl side-chains. This agent has reduced toxicity compared with doxorubicin, and is effective in the treatment of solid tumours and leukaemias. 

There are two major groups of synthetic compounds which have cannabin-oid activity, but which differ chemically from the tricyclic THC-like canna-binoids the bicyclic cannabinoids, exemplified by compound CP55940 (23), and the (aminoalkyl)indoles exemplified by pravadoline (24a). A detailed SAR analysis of these groups of compounds is beyond the scope of this review. The bicyclic cannabinoids and derivatives have been reviewed previously [105] recent publications deal mainly with related tricyclic non-classical cannabinoids [106] and with the (aminoalkyl)indoles [92, 107]. It is of interest to note that while the bicyclic cannabinoids were originally prepared as simplified cannabinoids, the cannabinoid-type activity of the (ami-noalkyl)indoles was discovered by serendipity. These compounds were synthesized in a project aimed at the discovery of novel nonsteroidal anti-inflammatory agents presumably based on the indomethacin structure. However, while they did not possess anti-inflammatory properties, they were found to be antinociceptive, and to inhibit the electrically evoked contractions in a mouse vas deferens muscle preparation. This led to binding experi-... 

Aminoalkyl-3, 4-dihydroquinoline derivatives, (VII), prepared by Jaroch (8) were effective as nitric oxide synthase inhibitors and used as anti-inflammatory agents. 

Barboiu M, Supuran CT, Menabuoni L, Scozzafava A, Mincione F, Briganti F, Mincione G (1999) Carbonic anhydrase inhibitors, synthesis of topically effective intraocular pressure lowering agents derived from 5-(aminoalkyl-carboxamido)-l,3,4-thiadiazole-2-sulfonamide. J Enz Inhib 15 23 -6... 

Singh. G. B. and Jetley, A., Studie,s on the aminoalkylation of some lactams as potential psyco pharmacological agents. I, Indian Drugs, 19, 1973. 

Sequestering agents, 3<5, 41. 228, 248. 2.59 Silicium compounds, 69 aminoalkyl silanes, 236 Silyl derivatives allyl-, 56... 

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