The Antiseptic Action of the Styryl-Pyridines and Styryl-Quinolines

Browning, C. H.; Cohen, Julius Berend; Ellingworth, S.; Gulbransen, R.

doi:10.1136/bmj.2.3269.326

Cited by 16 publications

(8 citation statements)

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“…Pyridinium derivatives have long been observed to exhibit antiseptic properties (Browning et al, 1923). Pyridinium chromophore compounds are particularly important because of their activity against methicillin-resistant Staphylococcus aureus (MRSA),which is a drug-resistant bacterium (Wainwright & Kristiansen, 2003;Chanawanno et al, 2010).…”

Section: Structure Descriptionmentioning

confidence: 99%

4-{(1E,3E)-4-[4-(Dimethylamino)phenyl]buta-1,3-dien-1-yl}-1-methylpyridin-1-ium iodide

Sundaram¹,

Sagayaraj²,

Raj³

et al. 2016

IUCr Data

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The title molecular salt, C18H21N2+·I−, consists of a pyridinium cation and an I−anion. The cation exists in anE,Econformation with respect to the two C=C double bonds, and is roughly planar with the pyridinium ring being inclined to the benzene ring by 10.8 (2) °. In the crystal, the ions are linked by a C—H...I hydrogen bond, and the cations are linked by C—H...π interactions, forming zigzag chains propagating along [010].

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Section: Structure Descriptionmentioning

confidence: 99%

4-{(1E,3E)-4-[4-(Dimethylamino)phenyl]buta-1,3-dien-1-yl}-1-methylpyridin-1-ium iodide

Sundaram¹,

Sagayaraj²,

Raj³

et al. 2016

IUCr Data

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“…Here, heterocyclic amines would be a great electron donating group thanks to their high electron density around nitrogen atom 5 [23,24]. Apart from that, heterocyclic amines have also makes their presences in various field from pharmaceutical to engineering and chemical sensing department [25,26,27,28,29,30,31,32]. Furthermore, a study regarding fluorescent probes [33] and NLO application for this compound has also been reported [34,35].…”

Section: Introductionmentioning

confidence: 99%

New styryl based organic chromophores including free amino and azomethine groups: Syntheses, photophysical, NLO and thermal properties

Putra¹,

Çakmaz²,

Seferoğlu³

et al. 2020

Preprint

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In this manuscript, we have successfully synthesized and characterized a new series of styryl based push-pull dyes containing free amino group and their Schiff bases derivatives in which dicyanomethylene was used as the acceptor group and different para-substituted alkylamines as the donor groups and 2-pyridyl as proton sensitive group. All compounds showed absorption in the visible region and green-red emission with low quantum yields. The photophysical properties were examined in various solvents with different polarities. The absorption and emission maxima were shifted bathocromically by increasing solvents polarity however, there was no regular correlation with polarity parameter. Significant red shifts were observed in the absorption and fluorescence emission maxima on increasing the electron-donating ability of the substituents. The observed color changes were photographed naked eyes and under illuminating UV-lamp. The pH sensitive properties of newly prepared Schiff bases against TBAOH were examined inside DMSO, furthermore their reserve protonation were also investigated using TFA. The structural and electronic properties of all newly synthesized compounds were studied using DFT calculation. In addition, NLO property of compounds were investigated by DFT. For determination thermal properties of all compounds were investigated and they showed good thermal stability up to 250 oC by TGA analyses under inert atmosphere. Our results indicate that the styryl based new push-pull dyes are promising candidate materials for NLO and pH applications.

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“…With Staphylococcus , however, the range of variation was distinctly less. Accordingly, the numerical values recorded here must be interpreted in the light of the above results (5). It should be noted, however, that in comparing certain closely related compounds in which marked alterations in antiseptic power may be produced by relatively slight chemical differences, e .…”

Section: Methods Of Estimating Antiseptic Powermentioning

confidence: 99%

“…Thus, the hydrochlorides of quinoline [3], tetrahydroquinoline [15], and the aminoquiuolines (o [4], m [ 6], p [ 8], and a [ 10] ), all f exceeding 1 : 2000 either in peptone water or in serum. The methochlorides of the aminoquinolines [7,9,11], except in the case of the ortho-compound [5], showed accentuation of antiseptic action in serum, as compared with the hydrochlorides of the corresponding bases, a characteristic result which will be discussed in more detail when dealing with the acridine group. [14] of the base do not show enhanced action.…”

Section: Fragments Of the Acridine Molecidementioning

confidence: 99%

Relationships between antiseptic action and chemical constitution with special reference to compounds of the pyridine, quinoline, acridine and phenazine series

Browning

Cohen

Gaunt

et al. 1922

Proc. R. Soc. Lond. B.

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In the course of investigations on the antiseptic properties of certain basic benzene derivatives, it was shown that the methochloride of diaminoacridine was very highly antiseptic, and that, unlike other powerful antiseptics then known, its antibacterial activity was not reduced by the presence of blood serum (Browning, Gilmour, Gulbransen, Kennaway and Thornton, 2, 7). Diaminoacridine methochloride had been prepared by Benda (1) for Ehrlich, and was named by them trypaflavin on account of its powerful therapeutic properties in experimental trypanosome infections. We are not aware that its action on bacteria had been investigated prior to the work recorded in the above paper (2), although Shiga (10) published almost simultaneously results of his investigations on its action on V. choleræ The hydrochloride and sulphate of diaminoacridine were then found to be practically equal to the methochloride in antiseptic properties and in efficacy of action in serum (8). In the case of these aminoacridine substances the power of killing bacteria is exerted slowly; thus, with the methochloride acting on B. coli in serum, the concentration which proves lethal in 2 hours (1:20000) is five to ten times greater than that required to produce sterility after 24 hours; on the other hand, mercuric chloride and carbolic acid produce their maximum effect within 2 hours, whether they be tested in a solution containing a minute amount of protein (0·7 per cent, of Witte’s peptone) or in a rich protein medium such as serum. The acridine compounds, therefore, may be said to act especially as bacteriostatic agents (7, 8). This property, coupled with their relative innocuousness for mammalian tissues, as tested by toxicity for the living animal as a whole (4, 7), effect on phagocytosis (3, 7), and slight irritating action on the conjunctiva (7), suggested that these substances should be specially applicable for the purpose of restraining bacterial infections in the tissues. Thus the methochloride, under the name of acriflavine, and the sulphate of diaminoacridine base, as proflavine, found extensive use in the treatment of infected wounds during the late war, and also in the treatment of such relatively accessible infections as gonorrhoea. The present work records the investigations which have been made with lire view of tracing the source of the antiseptic property of diaminoacridine compounds by examining substances which may be regarded as fragments of the acridine molecule. The parent substance of the acridine derivatives is a compound of the following formula that is, a combination of two benzene and a pyridine ring. If the two side wings are removed, a pyridine nucleus remains; if only one wing is detached, a quinoline nucleus results. It seemed, therefore, possible that the antiseptic activity of acriflavine (diamino acridine methochloride) might reside either in the pyridine or quinoline nucleus, reinforced by one or more amino groups. It is for this reason that substances of this type were first examined. In addition, a series of acridine derivatives have been prepared and tested for their antiseptic power in order to determine, if possible, whether any law could be established relating chemical structure and antiseptic action within the group. Also, observations have been made upon phenazine compounds, on account of their close chemical relationship to the acridine group.

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The Antiseptic Action of the Styryl-Pyridines and Styryl-Quinolines

Cited by 16 publications

References 0 publications

4-{(1E,3E)-4-[4-(Dimethylamino)phenyl]buta-1,3-dien-1-yl}-1-methylpyridin-1-ium iodide

4-{(1E,3E)-4-[4-(Dimethylamino)phenyl]buta-1,3-dien-1-yl}-1-methylpyridin-1-ium iodide

New styryl based organic chromophores including free amino and azomethine groups: Syntheses, photophysical, NLO and thermal properties

Relationships between antiseptic action and chemical constitution with special reference to compounds of the pyridine, quinoline, acridine and phenazine series

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