Microwave-assisted facile synthesis of 2-substituted 2-imidazolines

Pathan, Mohsin Y.; Paike, Vijaykumar V.; Pachmase, Pandurang R.; More, Sandeep; Ardhapure, S. S.; Pawar, Rajendra P.

doi:10.3998/ark.5550190.0007.f25

Cited by 7 publications

(6 citation statements)

References 6 publications

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“…Chemistry N-aryl-2-amino-3-cyanopyrroles 1a-d were obtained by reaction of a-hydroxy ketones (namely; benzoin or phenacyl bromide) with different aryl amine and malonodinitrile according to a procedure defined in the literature 50,64,65 . Reaction of nitriles, carboxylic acids, esters, ortho-esters or hydroxyamides with ethylenediamine, using carbon disulphide as solvent, is a well-known method for preparation of the corresponding 2-substituted imidazolines, as used here for the preparation of compounds 3-(2-dihydroimidazolyl)pyrrole-2-amines 2a-d [66][67][68][69] . The structures of these compounds were confirmed by spectral analysis; IR spectra showed disappearance of CN absorption bands and appearance of absorption frequency for NH at 3403-3290 cm À1 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

El-Hameed

Sayed

Ali

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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Pyrroles and its fused forms possess antimicrobial activities, they can easily interact with biomolecules of living systems. A series of substituted pyrroles, and its fused pyrimidines and triazines forms have been synthesised, all newly synthesised compound structures were confirmed by spectroscopic analysis. Generally, the compounds inhibited growth of some important human pathogens, the best effect was given by: 2a, 3c, 4d on Gram-positive bacteria and was higher on yeast ( C. albican s), by 5c on Gram-negative bacteria and by 5a then 3c on filamentous fungi (A. fumigatus and F. oxysporum ). Such results present good antibacterial and antifungal potential candidates to help overcome the global problem of antibiotic resistance and opportunistic infections outbreak. Compound 3c gave the best anti-phytopathogenic effect at a 50-fold lower concentration than Kocide 2000, introducing a safe commercial candidate for agricultural use. The effect of the compounds on DNA was monitored to detect the mode of action.

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Section: Resultsmentioning

confidence: 99%

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

El-Hameed

Sayed

Ali

et al. 2021

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…In contrast, these compounds and the new ones 18c – 18d were successfully prepared by us in quantitative yields via an adaptation of the protocol described by Fujioka [ 29 ]. Imidazoline derivatives 18e and 18f were synthesized in moderate yields by an adaptation of a procedure described in the literature [ 30 ]. All compounds were characterized by spectroscopic methods.…”

Section: Resultsmentioning

confidence: 99%

Imidazolines as Non-Classical Bioisosteres of N-Acyl homoserine lactones and Quorum Sensing Inhibitors

Reyes‐Arellano

Bucio-Cano

Montenegro-Sustaita

et al. 2012

IJMS

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A series of selected 2-substituted imidazolines were synthesized in moderate to excellent yields by a modification of protocols reported in the literature. They were evaluated as potential non-classical bioisosteres of AHL with the aim of counteracting bacterial pathogenicity. Imidazolines 18a, 18e and 18f at various concentrations reduced the violacein production by Chromobacterium violaceum, suggesting an anti-quorum sensing profile against Gram-negative bacteria. Imidazoline 18b did not affect the production of violacein, but had a bacteriostatic effect at 100 μM and a bactericidal effect at 1 mM. Imidazoline 18a bearing a hexyl phenoxy moiety was the most active compound of the series, rendering a 72% inhibitory effect of quorum sensing at 100 μM. Imidazoline 18f bearing a phenyl nonamide substituent presented an inhibitory effect on quorum sensing at a very low concentration (1 nM), with a reduction percentage of 28%. This compound showed an irregular performance, decreasing inhibition at concentrations higher than 10 μM, until reaching 100 μM, at which concentration it increased the inhibitory effect with a 49% reduction percentage. When evaluated on Serratia marcescens, compound 18f inhibited the production of prodigiosin by 40% at 100 μM.

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“…In addition to classical methods, 5,6 different procedures such as on a solid support, 7 solventfree, 8 sonochemical 9 and microwave-assisted methods are used in the synthesis of these compounds. 10,11 Besides, effective and new enantioselective methods have been improved for the synthesis of chiral imidazoline compounds over the last years. 12,13 Imidazoline compounds are widely studied by organic chemists with regard to their different application areas as synthetic intermediates, protecting groups, chiral auxiliaries and catalysts for asymmetric synthesis.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons

Ã‡apana¹,

Servi²

2018

Arkivoc

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Microwave-assisted facile synthesis of 2-substituted 2-imidazolines

Abstract: A novel method for the synthesis of 2-substituted 2-imidazolines under microwave irradiation is reported. The yields of product obtained using this protocol are significantly high and the reaction time is reduced.

Cited by 7 publications

References 6 publications

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

Synthesis of novel pyrroles and fused pyrroles as antifungal and antibacterial agents

Imidazolines as Non-Classical Bioisosteres of N-Acyl homoserine lactones and Quorum Sensing Inhibitors

Synthesis of novel C-2 substituted imidazoline derivatives having the norbornene/dibenzobarrelene skeletons

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