XXIII.—Chloro-derivatives of m-hydroxybenzaldehyde

Hodgson, Herbert H.; Beard, Herbert Greensmith

doi:10.1039/jr9262900147

Cited by 16 publications

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“…2,6-Dichloro-3-hydroxybenzonitrile. This was prepared from 2,6-dichloro-3-hydroxybenzaldehyde (Hodgson & Beard, 1926) as starting material. When the corresponding aldoxime (5.6g.)…”

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confidence: 99%

“…When the corresponding aldoxime (5.6g.) (Hodgson & Beard, 1926) was refluxed in 20ml. of acetic anhydride for 2hr.…”

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confidence: 99%

“…2,6-Dichloro-3-hydroxybenzoic acid. This was prepared by oxidation of 2,6 -dichloro -3 -hydroxybenzaldehyde (Hodgson & Beard, 1926) with freshly prepared Ag20 according to the method of Pearl (1950). 2,6-Dichloro-3-hydroxybenzoic acid crystallized from water, forming prisms of the monohydrate, m.p.…”

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The comparative metabolism of 2,6-dichlorothiobenzamide (Prefix) and 2,6-dichlorobenzonitrile in the dog and rat

Griffiths¹,

Moss²,

Rose³

et al. 1966

Biochemical Journal

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1. A single oral dose of either [(14)C]Prefix or 2,6-dichlorobenzo[(14)C]nitrile to rats is almost entirely eliminated in 4 days: 84.8-100.5% of (14)C from [(14)C]Prefix is excreted, 67.3-79.7% in the urine, and 85.8-97.2% of (14)C from 2,6-dichlorobenzo-[(14)C]nitrile is excreted, 72.3-80.7% in the urine. Only 0.37+/-0.03% of the dose of [(14)C]Prefix and 0.25+/-0.03% of the dose of 2,6-dichlorobenzo[(14)C]nitrile are present in the carcass plus viscera after removal of the gut. Rats do not show sex differences in the pattern of elimination of the respective metabolites of the two herbicides. The rates of elimination of (14)C from the two compounds in the 24hr. and 48hr. urines are not significantly different (P >0.05) from one another. 2. After oral administration to dogs, 85.9-106.1% of (14)C from [(14)C]Prefix is excreted, 66.6-80.9% in the urine, and 86.8-92.5% of (14)C from 2,6-dichlorobenzo[(14)C]nitrile is excreted, 60.0-70.1% in the urine. Dogs do not show sex differences in the pattern of eliminating the metabolites of either Prefix or 2,6-dichlorobenzonitrile. 3. Dogs and rats do not show species differences in the patterns of elimination of the two herbicides. 4. Prefix and 2,6-dichlorobenzonitrile are completely metabolized; unchanged Prefix and 2,6-dichlorobenzonitrile are absent from the urine and faeces, and from the carcasses when elimination is complete. In the hydrolysed urine of rats dosed with either [(14)C]Prefix or 2,6-dichlorobenzo[(14)C]nitrile, 2,6-dichloro-3-hydroxybenzonitrile accounts for approx. 42% of the (14)C, a further 10-11% is accounted for by 2,6-dichlorobenzamide, 2,6-dichlorobenzoic acid, 2,6-dichloro-3- and -4-hydroxybenzoic acid and 2,6-dichloro-4-hydroxybenzonitrile collectively, and 25-30% by six polar constituents, of which two are sulphur-containing amino acids. 5. In the unhydrolysed urines of rats dosed with either [(14)C]Prefix or 2,6-dichlorobenzo[(14)C]nitrile, there are present free 2,6-dichloro-3- and -4-hydroxybenzonitrile, their glucuronide conjugates, ester glucuronides of the principal aromatic acids that are present in the hydrolysed urines, and two sulphur-containing metabolites analogous to mercapturic acids or premercapturic acids. 6. Prefix is thus extensively transformed into 2,6-dichlorobenzonitrile: R.CS.NH(2)-->R.CN+H(2)S, where R=C(6)H(3)Cl(2). However, the competitive reaction: R.CS.NH(2)+H(2)O-->R.CO.NH(2)+H(2)S takes place to a very limited extent.

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“…2,6-Dichloro-3-hydroxybenzonitrile. This was prepared from 2,6-dichloro-3-hydroxybenzaldehyde (Hodgson & Beard, 1926) as starting material. When the corresponding aldoxime (5.6g.)…”

mentioning

confidence: 99%

“…When the corresponding aldoxime (5.6g.) (Hodgson & Beard, 1926) was refluxed in 20ml. of acetic anhydride for 2hr.…”

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confidence: 99%

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The comparative metabolism of 2,6-dichlorothiobenzamide (Prefix) and 2,6-dichlorobenzonitrile in the dog and rat

Griffiths¹,

Moss²,

Rose³

et al. 1966

Biochemical Journal

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“…Chlorination of 3‐methoxybenzaldehyde with N ‐chlorosuccinimide gives a mixture of products separable by silica chromatography. The first fraction is the aldehyde with an NMR spectrum corresponding to 2‐chloro‐5‐methoxybenzaldehyde ( 12 ), even though the melting point of the sample does not agree with the one reported from a previously described procedure (Scheme 3) (40).…”

Section: Resultsmentioning

confidence: 92%

In Vitro Photodynamic Activity of 5,15‐bis(3‐Hydroxyphenyl)porphyrin and Its Halogenated Derivatives Against Cancer Cells

Serra

Piñeiro

Santos

et al. 2010

Photochem & Photobiology

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5,15-Diarylporphyrins (1-5) with hydroxyl groups and halogens as substituents were prepared by condensation between unsubstituted dipyrromethane and halogenated m-hydroxybenzaldehydes. Photophysical properties show that the nonhalogenated porphyrin 1 has higher fluorescence yield but lower singlet oxygen formation quantum yield than the halogenated derivatives due to the heavy atom effect. The in vitro activity of these derivatives was tested against WiDr colorectal adenocarcinoma and A375 melanoma cancer cells. All porphyrins present a much higher phototoxicity than Photofrin with IC(50) values lower than the 50 nM level for WiDr cells and 25 nM level for A375 cancer cells. The most photoactive compound is the nonhalogenated porphyrin 1 which also presents the highest uptake. Halogenated derivatives present much lower uptakes than 1. However, their photoactivity is similar to compound 1 showing that their intrinsic photoactivity (ISP) is very high. Iodinated compound 4 presents the highest ISP. The greater ability of these porphyrins to destroy cancer cells could be related to their photophysical and photochemical properties.

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“…Reaction was performed according to the general procedure with 4 mmol of 1m and 2b (60 min). 1m was prepared by nitration of 2‐chlorobenzaldehyde . The mixture obtained after flash chromatography was dissolved in THF, mixed with Al 2 O 3 , and dried.…”

Section: Methodsmentioning

confidence: 99%

Facile and Regioselective Synthesis of Substituted 1H‐Pyrazolo[3,4‐b]quinolines from 2‐Fluorobenzaldehydes and 1H‐Pyrazol‐5‐amines

Szlachcic

Kucharek

Jarosz

et al. 2016

Journal of Heterocyclic Chem

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The present article concerns the scope and limitations of the regioselective condensation of 2‐fluorobenzaldehydes with 1H‐pyrazol‐5‐amines, leading to the synthesis of substituted 1H‐pyrazolo[3,4‐b]quinolines (PQ), in the presence of a base catalyst (DABCO and 2,4,6‐trimethylpyridine). A method to obtain these nitrogen heterocycles with fluorine or trifluoromethyl substituents in different positions in the carbocyclic ring was developed as a part of a systematic research on the influence of fluorine‐containing substituents on the parameters of PQ. Those compounds, characterized by high‐fluorescence intensity, have been tested as emitters for the organic light‐emitting diodes since 1997. The functionalization of PQ causes changes in various parameters, for example, HOMO and LUMO levels, which are important for the adjustment of fabricated organic light‐emitting diodes. One of the easiest methods of PQ preparation, namely, the condensation of substituted anilines with 5‐chloro‐1H‐pyrazole‐4‐carbaldehydes, is not regioselective. The method described in this study allows synthesizing of 1H‐pyrazolo[3,4‐b]quinolines with good yields and high selectivity – only the expected isomer is obtained. As various different 2‐fluorobenzaldehydes are commercially available, and 1H‐pyrazol‐5‐amines with different substituents are easy to prepare, the method could be a good alternative to the already known procedures. All possible mechanisms of the reaction were also thoroughly studied.

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XXIII.—Chloro-derivatives of m-hydroxybenzaldehyde

Cited by 16 publications

References 0 publications

The comparative metabolism of 2,6-dichlorothiobenzamide (Prefix) and 2,6-dichlorobenzonitrile in the dog and rat

The comparative metabolism of 2,6-dichlorothiobenzamide (Prefix) and 2,6-dichlorobenzonitrile in the dog and rat

In Vitro Photodynamic Activity of 5,15‐bis(3‐Hydroxyphenyl)porphyrin and Its Halogenated Derivatives Against Cancer Cells

Facile and Regioselective Synthesis of Substituted 1H‐Pyrazolo[3,4‐b]quinolines from 2‐Fluorobenzaldehydes and 1H‐Pyrazol‐5‐amines

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