Applications of Mannich Reaction/Formation of Gramine/Formation of aminoalkyl derivatives
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4 سال پیش
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Mannich bases are the end
Mannich bases are the end products of Mannich reaction and are known as beta-amino ketone carrying compounds. Mannich reaction is a carbon-carbon bond forming nucleophilic addition reaction and is a key step in synthesis of a wide variety of natural products, pharmaceuticals, and so forth. Mannich reaction is important for the construction of nitrogen containing compounds. There is a number of aminoalkyl chain bearing Mannich bases like fluoxetine, atropine, ethacrynic acid, trihexyphenidyl, and so forth with high curative value. The literature studies enlighten the fact that Mannich bases are very reactive and recognized to possess potent diverse activities like anti-inflammatory, anticancer, antifilarial, antibacterial, antifungal, anticonvulsant, anthelmintic, antitubercular, analgesic, anti-HIV, antimalarial, antipsychotic, antiviral activities and so forth. The biological activity of Mannich bases is mainly attributed to α, β-unsaturated ketone which can be generated by deamination of hydrogen atom of the amine group.
1. Introduction
Mannich bases, beta-amino ketones carrying compounds, are the end products of Mannich reaction [1, 2]. Mannich reaction is a nucleophilic addition reaction which involves the condensation of a compound with active hydrogen(s) with an amine (primary or secondary) and formaldehyde (any aldehyde) [3]. The schematic representation of general Mannich reaction is given in Scheme 1.
Scheme 1
Mannich bases also act as important pharmacophores or bioactive leads which are further used for synthesis of various potential agents of high medicinal value which possess aminoalkyl chain. The examples of clinically useful Mannich bases which consist of aminoalkyl chain are cocaine, fluoxetine, atropine, ethacrynic acid, trihexyphenidyl, procyclidine, ranitidine, biperiden [4–6], and so forth. Mannich bases are known to play a vital role in the development of synthetic pharmaceutical chemistry. The literature studies revealed that Mannich bases are very reactive and can be easily converted to other compounds, for example, reduced to form physiologically active amino alcohols [7]. Mannich bases are known to possess potent activities like anti-inflammatory [8, 9], anticancer [10, 11], antifilarial [8], antibacterial [12, 13], antifungal [13, 14], anticonvulsant [15], anthelmintic [16], antitubercular [17, 18], analgesic [19], anti-HIV [17], antimalarial [20], antipsychotic [21], antiviral [22] activities and so forth. Along with biological activities Mannich bases are also known for their uses in detergent additives [23], resins, polymers, surface active agents [24], and so forth. Prodrugs of Mannich bases of various active compounds have been prepared to overcome the limitations [25]. Mannich bases (optically pure chiral) of 2-naphthol are employed for catalysis (ligand accelerated and metal mediated) of the enantioselective carbon-carbon bond formation. Mannich bases and their derivatives are intermediates for the synthesis of bioactive molecules [26, 27]. Mannich reaction is widely used for the construction of nitrogen containing compounds [28]. Mannich bases have gained importance due to their application in antibacterial activity [29] and other applications are in agrochemicals such as plant growth regulators.
1. Introduction
Mannich bases, beta-amino ketones carrying compounds, are the end products of Mannich reaction [1, 2]. Mannich reaction is a nucleophilic addition reaction which involves the condensation of a compound with active hydrogen(s) with an amine (primary or secondary) and formaldehyde (any aldehyde) [3]. The schematic representation of general Mannich reaction is given in Scheme 1.
Scheme 1
Mannich bases also act as important pharmacophores or bioactive leads which are further used for synthesis of various potential agents of high medicinal value which possess aminoalkyl chain. The examples of clinically useful Mannich bases which consist of aminoalkyl chain are cocaine, fluoxetine, atropine, ethacrynic acid, trihexyphenidyl, procyclidine, ranitidine, biperiden [4–6], and so forth. Mannich bases are known to play a vital role in the development of synthetic pharmaceutical chemistry. The literature studies revealed that Mannich bases are very reactive and can be easily converted to other compounds, for example, reduced to form physiologically active amino alcohols [7]. Mannich bases are known to possess potent activities like anti-inflammatory [8, 9], anticancer [10, 11], antifilarial [8], antibacterial [12, 13], antifungal [13, 14], anticonvulsant [15], anthelmintic [16], antitubercular [17, 18], analgesic [19], anti-HIV [17], antimalarial [20], antipsychotic [21], antiviral [22] activities and so forth. Along with biological activities Mannich bases are also known for their uses in detergent additives [23], resins, polymers, surface active agents [24], and so forth. Prodrugs of Mannich bases of various active compounds have been prepared to overcome the limitations [25]. Mannich bases (optically pure chiral) of 2-naphthol are employed for catalysis (ligand accelerated and metal mediated) of the enantioselective carbon-carbon bond formation. Mannich bases and their derivatives are intermediates for the synthesis of bioactive molecules [26, 27]. Mannich reaction is widely used for the construction of nitrogen containing compounds [28]. Mannich bases have gained importance due to their application in antibacterial activity [29] and other applications are in agrochemicals such as plant growth regulators.
4 سال پیش
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