Novel multicomponent reactions involving isoquinoline or phenanthridine and activated acetylenic ester in the presence of heterocyclic NH or 1,3-dicarbonyl compounds

Abstract In living systems, nucleophilic amino acid residues are prone to non-enzymatic post-translational modification by electrophiles. α-Dicarbonyl compounds are a special type of electrophiles that can react irreversibly with lysine, arginine, and cysteine residues via complex mechanisms to form post-translational modifications known as advanced glycation end-products (AGEs). Glyoxal, methylglyoxal, and 3-deoxyglucosone are the major endogenous dicarbonyls, with methylglyoxal being the most well-studied. There are several routes that lead to the formation of dicarbonyl compounds, most originating from glucose and glucose metabolism, such as the non-enzymatic decomposition of glycolytic intermediates and fructosyl amines. Although dicarbonyls are removed continuously mainly via the glyoxalase system, several conditions lead to an increase in dicarbonyl concentration and thereby AGE formation. AGEs have been implicated in diabetes and aging-related diseases, and for this reason the elucidation of their structure as well as protein targets is of great interest. Though the dicarbonyls and reactive protein side chains are of relatively simple nature, the structures of the adducts as well as their mechanism of formation are not that trivial. Furthermore, detection of sites of modification can be demanding and current best practices rely on either direct mass spectrometry or various methods of enrichment based on antibodies or click chemistry followed by mass spectrometry. Future research into the structure of these adducts and protein targets of dicarbonyl compounds may improve the understanding of how the mechanisms of diabetes and aging-related physiological damage occur.

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Dibenzo-1,5-diazocine-2,6-dione, 2-Iminoindolin-3-one and N-(Carbamoylmethyl)-aminobenzoic Acid Ester from Aminobenzoic Acid by Multicomponent Reactions

Tetrahedron ◽

10.1016/s0040-4020(98)00718-2 ◽

1998 ◽

Vol 54 (31) ◽

pp. 11887-11898 ◽

Cited By ~ 1

Author(s):

B Ebert

Keyword(s):

Acid Ester ◽

Multicomponent Reactions ◽

Aminobenzoic Acid

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Multicomponent Reactions, Volume 2

10.1055/b-003-125831 ◽

2014 ◽

Cited By ~ 1

Keyword(s):

Multicomponent Reactions

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Reactivity of Barbituric, Thiobarbituric Acids and Their Related Analogues: Synthesis of Substituted and Heterocycles-based Pyrimidines

Current Organic Chemistry ◽

10.2174/1385272824999200608134859 ◽

2020 ◽

Vol 24 (14) ◽

pp. 1610-1642 ◽

Cited By ~ 1

Author(s):

Ahmed El-Mekabaty ◽

Hassan A. Etman ◽

Ahmed Mosbah ◽

Ahmed A. Fadda

Keyword(s):

Xanthine Oxidase ◽

Multicomponent Reactions ◽

Biological Activities ◽

Present Review ◽

Urease Inhibitors ◽

Effective Catalyst ◽

Inhibitory Activities ◽

Catalyst Reusability ◽

High Yields ◽

Nano Catalysts

Barbituric, thiobarbituric acids and their related analogs are reactive synthons for the synthesis of drugs and biologically, and pharmaceutically active pyrimidines. The present review aimed to summarize the recent advances in the synthesis of different alkylsubstituted, fused cycles, spiro-, and binary heterocycles incorporated pyrimidine skeleton based on barbituric derivatives. In this sequence, the eco-friendly techniques under catalytic conditions were used for the diverse types of multicomponent reactions under different conditions for the synthesis of various types of heterocycles. Nano-catalysts are efficient for the synthesis of these compounds in high yields and effective catalyst reusability. The compounds are potent antibacterial, cytotoxic, xanthine oxidase inhibitory activities, and attend as urease inhibitors. The projected mechanisms for the synthesis of pyranopyrimidines, benzochromenopyrimidines, chromeno-pyranopyrimidines, spiroxyindoles, oxospiro-tricyclic furopyrimidines, pyrimidine-based monoand bicyclic pyridines were discussed. The potent and diverse biological activities for instance, antioxidant, antibacterial, cytotoxic, and xanthine oxidase inhibitory activities, as well as urease inhibitors, are specified.

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