59. Three new analogues of chloramphenicol

Buu‐Hoï, Ng. Ph.; Xuong, Ng. D.; Khôi, Ng. H.

doi:10.1039/jr9510000255

Cited by 3 publications

(1 citation statement)

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“…To circumvent formation of this undesired impurity, the synthetic approach was modified according to After purification by liquid chromatography a yield of 52% pure product was obtained. Further reaction of 16 with bromine in 1 % HBr/acetic acid solution gave 2-bromo-2',4'-dichloro-[ring U-14C]acetophenone 17 (7) in 55% yield after liquid chromatography purification. Unreacted 16 was brominated again in order to increase the total yield of this step to 80%.…”

Section: 3-dichl0ro-[u-~~c]benzenementioning

confidence: 99%

The synthesis of [U‐¹⁴C phenyl] LS 840606, an agricultural fungicide

Madegard

Mestre

Raimond

et al. 1995

Labelled Comp Radiopharmac

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2,2′4′‐Trichloro‐[ring U‐14C]acetophenone 3 was the key intermediate of this synthesis patterned after the industrial route. An unexpected poor yield was observed during the preparation of 3 by the Friedel‐Crafts reaction of chloroacetyl chloride with 1,3‐dichloro‐[U‐14C]benzene 10, possibly the result of an isotope effect although this poor yield might be explained by other factors. Two routes were checked for the preparation of 1,3‐dichloro‐[U‐14C]benzene 10. The action of CCL4 with 1,3‐dinitro‐[U‐14C]benzene at 280°C was entailed with explosions. A safer route started from [U‐14C]aniline via 2,4‐dichloro‐[ring U‐14C]acetanilide. Friedel‐Crafts reaction of 10 with acetyl chloride gave rise in 52% yield to 2′,4′‐dichloro‐[ring U‐14C]acetophenone 16 which was brominated to 2‐bromo‐2′,4′‐dichloro‐[ring U‐14C]acetophenone 17;17 was condensed with 2,2‐(ethylenedioxy)ethylmagnesium bromide to compound 18; 18 was condensed with 1,2,4‐triazole to 5 then successively treated with HCl:water:dioxane and 2,2,2‐trifluoroethanol/HCl. Separation of the two diastereomers by medium pressure liquid chromatography. 7% overall radioactive yield from [U‐14C]aniline. Radiochemical purity 99%.

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Section: 3-dichl0ro-[u-~~c]benzenementioning

confidence: 99%

The synthesis of [U‐¹⁴C phenyl] LS 840606, an agricultural fungicide

Madegard

Mestre

Raimond

et al. 1995

Labelled Comp Radiopharmac

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Efficient synthesis of 14‐substituted‐14‐H‐dibenzo[a,j]xanthenes using silica supported sodium hydrogen sulfate or amberlyst‐15 catalyst

Kumar

Srinivas

Sadhu

et al. 2009

Journal of Heterocyclic Chem

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magnified imageSilica supported sodium hydrogen sulfate (NaHSO4·SiO2) or amberlyst‐15 acts as an efficient heterogeneous catalyst for the preparation of 14‐alkyl and aryl‐14‐H‐dibenzo[a,j]xanthenes with various aldehydes and β‐naphthol in dichloroethane solvent in excellent yields. Synthesis of three new compounds are reported using this methodology. Recyclable nature of the amberlyst‐15 catalyst was also studied and the catalyst can be reused. J. Heterocyclic Chem., (2009).

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Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain

Vunnam

Radin

1980

Chemistry and Physics of Lipids

123

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In a search for potent inhibitors of glucocerebroside biosynthesis, we synthesized aromatic analogs of the enzyme's substrate, ceramide, many of which have not previously been described in the literature. Mouse brain and spleen, rat brain, and human placenta and spleen were all found to be susceptible to inhibition by a variety of compounds, although to differing extents. The most potent inhibitor was 2-decanoylamino-3-morpholino-1-phenylpropanol. The dehydro version of this compound (2-decanoylamino-3-morpholinopropiophenone) was less effective but it produced inactivation of the enzyme, probably by covalent reaction with the enzyme's active site. Examination of the various effects seen leads us to suggest that the active region of the enzyme contains four recognitional sites: an anionic moiety that may bind the glucose in activated form, an oxygen-binding region oriented toward the third carbon atom of ceramide, a narrow region that binds the alkyl chain of the fatty acid moiety, and a less narrow region that binds the hydrocarbon chain of the sphingoid base moiety.

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59. Three new analogues of chloramphenicol

Cited by 3 publications

References 0 publications

The synthesis of [U‐¹⁴C phenyl] LS 840606, an agricultural fungicide

The synthesis of [U‐¹⁴C phenyl] LS 840606, an agricultural fungicide

Efficient synthesis of 14‐substituted‐14‐H‐dibenzo[a,j]xanthenes using silica supported sodium hydrogen sulfate or amberlyst‐15 catalyst

Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain

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59. Three new analogues of chloramphenicol

Cited by 3 publications

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The synthesis of [U‐14C phenyl] LS 840606, an agricultural fungicide

The synthesis of [U‐14C phenyl] LS 840606, an agricultural fungicide

Efficient synthesis of 14‐substituted‐14‐H‐dibenzo[a,j]xanthenes using silica supported sodium hydrogen sulfate or amberlyst‐15 catalyst

Analogs of ceramide that inhibit glucocerebroside synthetase in mouse brain

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The synthesis of [U‐¹⁴C phenyl] LS 840606, an agricultural fungicide

The synthesis of [U‐¹⁴C phenyl] LS 840606, an agricultural fungicide