Chemistry of 2-Amino-3-cyanopyridines (original) (raw)
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Facile synthesis and antiproliferative activity of new 3-cyanopyridines
BMC Chemistry
Background Pyridines have been reported to possess various pharmacological activities. Results Sodium 3-oxo-3-(2-oxo-2H-chromen-3-yl)prop-1-en-1-olate (2) and sodium 3-oxo-3-(3-oxo-3H-benzo[f]chromen-2-yl)prop-1-en-1-olate (7) were prepared and reacted with 2-cyano-N’-(1-aryl(heteryl)ethylidene)acetohydrazides 3a–d to produce 2-oxo-1,2-dihydropyridine-3-carbonitrile derivatives 5a–d and 9a–d, respectively, in good yields. Also, 3a–d reacted with sodium (2-oxocyclopentylidene)methanolate (11a) or sodium (2-oxocyclohexylidene) methanolate (11b) to yield 2-oxo-tetrahydro-1H-cyclopenta[b]pyridine-3-carbonitriles 13a–d and 2-oxo-hexahydroquinoline-3-carbonitriles 13e–h, respectively. The mechanisms that account for the formation of the products are discussed. Additionally, the structures of all the newly synthesized products are confirmed, based on elemental analysis and spectral data. Several of the newly synthesized compounds are evaluated for their antitumor activity against HEPG2 and...
Synthesis and Characterization of New Heterocyclic Compounds Derived from 2-Aminopyridine
European Journal of …, 2009
New Schiff's bases with 1,2,4-triazole ring (3a-j) have been synthesized from 4-(4'-amino-5mercapto-4H-1, 2, 4-triazol-3-yl) phenol (2) which is obtained from 4-hydroxybenzohydrazide (1) by a cyclization reaction. Infrared spectroscopy and 1 H NMR spectroscopy were used to characterize the structure of synthesized compounds. All the final products are indicated as ketoenol and thione-thiol tautomers.
A Simple and Efficient Synthesis of Cynopyridines
The pyridine skeleton is of great importance to chemists as well as to biologists as it is found in a large variety of naturally occurring compounds and also in clinically useful molecules having diverse biological activities. The pyridine ring systems have emerged as integral backbones of over 7000 existing drugs [1, 2]. The pyridine ring is also an integral part of anticancer and anti-inflammatory agents [3].
Syntheses, Complexation and Biological Activity of Aminopyridines: A Mini-Review
2021
Aminopyridines are among the classes of heterocyclic compounds that have been extensively studied in the last few decades owing to their interesting biological activities. They exist in three isomeric forms: 2-aminopyridine, 3-aminopyridine and 4-aminopyridine. The diversity in their pharmacological activities has attracted the attention of many researchers to explore the reasons for their wide potential. This study examines recent advances related to the efficient procedure for synthesizing different types of aminopyridine derivatives, its coordination site with metals and biological activities using systematic literature review and content analysis. Other important concepts of aminopyridines discussed are basicity, electric hindrance as related to percentage yield of isomeric forms and spectra updates on the characterization of aminopyridines. The findings from this study also reveal the array of solvents used for purification processes; ideas on isomers that have not been used in...
Journal of Heterocyclic Chemistry, 2013
in Wiley Online Library (wileyonlinelibrary.com). 1-Pyridin-3-yl-3-(2-thienyl of 2-furyl)prop-2-en-1-ones 1a,b reacted with 2-cyanoethanethioamide (2) to afford the corresponding 4-(thiophen-2-yl or furan-2-yl)-6-sulfanyl-2,3′-bipyridine-5-carbonitriles 3a,b. The synthetic potentiality of compounds 3a,b were investigated in the present study via their reactions with several active halogen containing compounds 4a-h. Our aim here is the synthesis of 4-(2-thienyl or 2furyl)-6-pyridin-3-ylthieno[2,3-b]pyridin-3-amines 6a-e,g-n via 6-(alkyl-thio)-4-(2-thienyl or 2-furyl)-2,3′-bipyridine-5-carbonitriles 5a-e,i-m. The structures of all newly synthesized heterocyclic compounds were elucidated by considering the data of IR, 1 H-NMR, mass spectra, as well as that of elemental analyses. Anti-cancer, anti-Alzheimer, and anti-COX-2 activities were investigated for all the newly synthesized heterocyclic compounds.
Solventless convenient synthesis of new cyano-2-aminopyridine derivatives from enaminonitriles
Tetrahedron Letters, 2013
A synthesis of novel 4-substituted-3-cyano-2-aminopyridines using enaminonitriles and various primary amines was established under microwave irradiation and solvent-free conditions. Structures of the new compounds were characterized by IR, MS, 1 H and 13 C NMR data and the structure of 2-aminopyridine of the products was confirmed by X-ray analysis.
Efficient Multicomponent Catalyst-Free Synthesis of Substituted 2-Aminopyridines
Chemistry Proceedings
2-aminopyridines scaffolds are an important class of nitrogen heterocyclic compounds with a wide range of biological activities. Multicomponent reactions (MCRs) are useful methods for the construction of nitrogen heterocyclic compounds. In this context, syntheses of 2-aminopyridines derivatives via MCRs have attracted considerable attention in recent years. We present, in this work, a rapid and efficient synthesis of 2-aminopyridine derivatives, via the catalyst-free four-component method. This protocol provides a simple and practical approach to functionalized 2-aminopyridnes from readily available substrates under solvent-free conditions.
Molecules
A new and suitable multicomponent one-pot reaction was developed for the synthesis of 2-amino-3-cyanopyridine derivatives. Background: This synthesis was demonstrated by the efficient and easy access to a variety of substituted 2-aminopyridines using enaminones as key precursors under solvent-free conditions. Methods: A range of spectroscopic techniques was used to determine and confirm the chemical structures (FTIR, 1H NMR, 13C NMR). The antimicrobial potency of synthesized compounds (2a–d) was tested using disk diffusion assays, and the Minimum Inhibitory Concentration (MIC) for the active compounds was determined against a panel of microorganisms, including Gram-positive and Gram-negative bacteria and yeasts. Moreover, a docking analysis was conducted by Molecular Operating Environment (MOE) software to provide supplementary information about the potential, as well as an ADME-T prediction to describe the pharmacokinetic properties of the best compound and its toxicity. Results: T...
Synthesis and evaluation of a series of aminocyanopyridines as antimicrobial agents
Medicinal Chemistry Research, 2011
With the aim of developing potential antimicrobials, a series of 2-amino-3-cyanopyridines incorporating both sulfur and oxygen as part of the heteroaromatic ring (methyl thiophene, methyl furan) and fused cycloalkane groups were synthesized and characterized by FTIR, 1H-NMR, 13C-NMR, and bases of elemental analysis. All synthesized compounds were evaluated for their in vitro antibacterial and antifungal activity. Antibacterial and antifungal activities of aminocyanopyridines against Pseudomonas aeruginosa ATCC 29212, Bacillus subtilis RSKK 244, Bacillus megaterium (clinical isolate), the gram-positive bacterium Micrococcus luteus NRRLB 4375, and the fungus Candida albicans ATCC 90028 were studied. The relationship between the functional-group variation and the biological activity of the evaluated compounds is discussed.