An eco-friendly water mediated synthesis of 1,2,3-triazolyl-2-aminopyrimidine hybrids as highly potent anti-bacterial agents

Nagarajan, Sangaraiah; Shanmugavelan, Poovan; Sathishkumar, Murugan; Selvi, R. Senthamizh; Ponnuswamy, Alagusundaram; Harikrishnan, Hariharan; Shanmugaiah, Vellasamy

doi:10.1016/j.cclet.2013.12.017

Cited by 26 publications

(9 citation statements)

References 30 publications

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“…Then, the reaction mixture was poured onto excess crushed ice and neutralized with dilute hydrochloric acid. The precipitated 4-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-6-(3-methoxyphenyl)pyrimidin-2-amine was filtered and recrystallized from ethanol 10 . Needle like colourless single crystals of the title compound used in X-ray diffraction studies were grown in an ethanolic solution by slow evaporation of the solvent at room temperature and collected in 78% yield.…”

Section: Synthesis Ofmentioning

confidence: 99%

“…The title compound has been synthesized and antibacterial activities are reported by our co-authors 10 . In this paper, we report the synthesis, crystal structure of 4-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-6-(3-methoxyphenyl) pyrimidin-2-amine (C 21 H 20 N 6 O), as well as theoretical studies using the DFT(B3LYP) method and 6-311G(d,p) basis set.…”

Section: Introductionmentioning

confidence: 99%

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Crystal Structure and DFT Studies of 4-(1-Benzyl-5-Methyl-1h-1,2,3-Triazol-4-Yl)-6-(3- Methoxyphenyl)pyrimidin-2-Amine

Murugavel¹,

Vijayakumar²,

Nagarajan³

et al. 2014

J. Chil. Chem. Soc.

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The title compound 1, 4-(1-benzyl-5-methyl-1H-1,2,3-triazol-4-yl)-6-(3-methoxyphenyl)pyrimidin-2-amine (C 21 H 20 N 6 O), was synthesized and structurally characterized by elemental analysis, 1 H NMR, 13 C NMR and single crystal X-ray diffraction. The molecular conformation is stabilized by an intramolecular C-H…N hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked by two pairs of inversion-related amine N-H N and C-H N hydrogen bonds, each generating alternate R 2 2 (8) ring motifs in a zigzag supramolecular chain that runs along c-axis. These chains stack along a-axis via amine N-H…O hydrogen bonds forming a two-dimensional supramolecular network. Density functional theory calculations of the structure, Mulliken population analyses on atomic charges and thermodynamic functions of the title compound were performed by using (DFT/B3LYP) method with the 6-311G(d,p) basis set level. The charge energy distribution and site of chemical reactivity of molecules were obtained by mapping electron density isosurface with electrostatic potential surfaces. The thermo dynamical properties of the title compound at different temperature have been calculated and corresponding relations between the properties and temperature have also been obtained.

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Section: Synthesis Ofmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Crystal Structure and DFT Studies of 4-(1-Benzyl-5-Methyl-1h-1,2,3-Triazol-4-Yl)-6-(3- Methoxyphenyl)pyrimidin-2-Amine

Murugavel¹,

Vijayakumar²,

Nagarajan³

et al. 2014

J. Chil. Chem. Soc.

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“…It has been reported that the combination of two heterocyclic skeletons having different biological functions produce new hybrid compounds that are more medically effective than their parent molecules [10]. In this regard, we have reported commendable bioactivities of 1,2,3-triazolyl-2-aminopyrimidine hybrids and 1,2,3-triazolyl dihydropyrimidine-2-thione hybrids [11,12].…”

Section: Introductionmentioning

confidence: 93%

Water mediated one-pot synthesis and biological evaluation of 1,2,3-triazolyl-1,4-dihydropyridine hybrids

et al. 2016

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Design and synthesis of a new series of 1,2,3-triazolyl-1,4-dihydropyridine hybrids (5a-5l) have been accomplished by a one-pot multicomponent reaction of opropargyl salicylaldehyde/o-propargyl naphthaldehyde, b-keto compounds, ammonium acetate, and organic azides in short reaction times. In vitro antibacterial studies of the newly synthesized hybrids were investigated against four different human pathogens, viz. S. aureus, Proteus mirabilis, E. Coli, and K. Pnemonia, and the results were compared with that of the standard drug, tetracycline. Also, their anti-inflammatory activity was studied against bovine serum albumin (BSA) and compared with that of the reference drug, dichlofenac. Some of the hybrids show good antibacterial and antiinflammatory activities comparable with that of the reference drugs.Electronic supplementary material The online version of this article (

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“…With this in mind, we have recently reported the synthesis of various bioactive hybrids linking 1,2,3‐triazole with many other heterocycles such as indoles, pyrazolines, N ‐acyl pyrazolines, pyrimidine‐2‐thiones, 2‐aminopyrimidines and pyridine from easily accessible 1,2,3‐triazole‐chalcones via environ‐friendly, greener pathways.…”

Section: Introductionmentioning

confidence: 99%

A Green and Efficient Synthesis of Bioactive 1, 2, 3 ‐ Triazolyl‐Pyridine/Cyanopyridine Hybrids via One‐Pot Multicomponent Grinding Protocol

et al. 2018

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A green and efficient synthesis of bioactive 1,2,3‐triazolyl‐pyridine/cyanopyridine hybrids has been achieved from easily accessible starting materials via one‐pot sequential multicomponent reaction under grinding strategy at room temperature in good to excellent yields. All the synthesized hybrids were evaluated for their antimicrobial activities against three human bacterial pathogens viz. Staphylococcus aureus, Salmonella typhi and Escherichia coli. The 1,2,3‐triazolyl cyanopyridine hybrids with 4‐chlorophenyl (5 c) and 2‐methylphenyl (5 e) substituents and the thiophenyl substituted 1,2,3‐triazolyl pyridine hybrid (5 s) showed remarkable activity better than tetracycline (standard drug). Also the selected compounds were screened for their antioxidant activity in the assay by 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) method.

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An eco-friendly water mediated synthesis of 1,2,3-triazolyl-2-aminopyrimidine hybrids as highly potent anti-bacterial agents

Cited by 26 publications

References 30 publications

Crystal Structure and DFT Studies of 4-(1-Benzyl-5-Methyl-1h-1,2,3-Triazol-4-Yl)-6-(3- Methoxyphenyl)pyrimidin-2-Amine

Crystal Structure and DFT Studies of 4-(1-Benzyl-5-Methyl-1h-1,2,3-Triazol-4-Yl)-6-(3- Methoxyphenyl)pyrimidin-2-Amine

Water mediated one-pot synthesis and biological evaluation of 1,2,3-triazolyl-1,4-dihydropyridine hybrids

A Green and Efficient Synthesis of Bioactive 1, 2, 3 ‐ Triazolyl‐Pyridine/Cyanopyridine Hybrids via One‐Pot Multicomponent Grinding Protocol

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