Natrium‐skatylsulfonat, ein Antagonist von Heteroauxin beim Wurzelwachstum

Wieland, Theodor; Fischer, E.; Moewus, Franz

doi:10.1002/jlac.19495610106

Cited by 13 publications

(7 citation statements)

References 13 publications

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“…Although compound 7 was previously synthesized by treatment of gramine with a sodium sulfite solution 48 , 49 or the sulfomethylation of indole with formaldehyde and sodium sulfite 50 and 8 was obtained from aerobic oxidation of indole-3-acetic acid with bisulfite 51 , 52 , 53 , the two compounds have never been isolated from a natural source. Thus, they are new natural products.…”

Section: Resultsmentioning

confidence: 99%

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Indole alkaloid sulfonic acids from an aqueous extract of Isatis indigotica roots and their antiviral activity

Meng

Guo

Liu

et al. 2017

Acta Pharmaceutica Sinica B

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Six new indole alkaloid sulfonic acids (1–6), together with two analogues (7 and 8) that were previously reported as synthetic products, were isolated from an aqueous extract of the Isatis indigotica root. Their structures including the absolute configurations were determined by spectroscopic data analysis, combined with enzyme hydrolysis and comparison of experimental circular dichroism and calculated electronic circular dichroism spectra. In the preliminary assay, compounds 2 and 4 showed antiviral activity against Coxsackie virus B3 and influenza virus A/Hanfang/359/95 (H3N2), respectively.

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Section: Resultsmentioning

confidence: 99%

“…Thus, they are new natural products. The detailed spectroscopic data of 7 and 8 are included in this paper since these data are absent in the literatures 48 , 49 , 50 , 51 , 52 , 53 .…”

Section: Resultsmentioning

confidence: 99%

Indole alkaloid sulfonic acids from an aqueous extract of Isatis indigotica roots and their antiviral activity

Meng

Guo

Liu

et al. 2017

Acta Pharmaceutica Sinica B

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“…Sodium (indol-3-yl)methanesulfonate (1a) was obtained from gramine as previously described. 4,5 NMR spectra were recorded on a Varian VXR-400 instrument at 400 MHz ( 1 H NMR) in CD 3 OD, DMSO-d 6, or CDCl 3 using these solvents as internal standards [CDCl 3 : δ 1 H (residual) = 7.25, CD 3 OD: δ 1 H (residual) = 3.32, DMSO-d 6 : δ 1 H (residual) = 2.50]. Melting points were determined on a Büchi SMP-20 apparatus and are uncorrected.…”

Section: Reaction Of 13 and N-tert-butylmethanesulfonamidementioning

confidence: 99%

“…Initially, we sought an apparently direct route to this compound from sodium (indol-3-yl)methanesulfonate (1a). The synthesis of 1a from gramine has been described about 50 years ago, 4 however, no data about amides and other derivatives of this sulfonic acid have been published. Our first approach (pathway 1 in Scheme 1) was based on the attempt to transform 1a into the corresponding sulfonyl chloride 2a and then into sulfonamide 3a.…”

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confidence: 99%

Synthesis of (Indol-3-yl)methanesulfonamide and its 5-Methoxy Derivative

Королев¹,

Shchekotikhin²,

Lysenkova³

et al. 2003

Synthesis

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Two methods for the synthesis of (indol-3-yl)methanesulfonamide were elaborated based on the 'switching off' the reactivity of the indole nucleus in the intermediates by using indoline or indoxyl compounds. (2,3-Dihydroindol-3-yl)methanesulfonic acid was the key compound used in the indole-indoline approach and (1-acetyl-3-hydroxy-2,3-dihydroindol-3-yl)-N-(tert-butyl)methanesulfonamide was the key intermediate when 1-acetylindoxyl was used as the starting compound. (1-Acetyl-3-hydroxy-2,3-dihydroindol-3-yl)-N-(tert-butyl)methanesulfonamide (15)A 2.5 M solution of BuLi (17 mL, 43 mmol) was slowly added to a stirred solution of i-Pr 2 NH (6.5 mL, 46 mmol) in anhyd THF (40 mL) at -78 °C in a stream of argon. The mixture was slowly warmed up to 0 °C and then cooled again to -78 °C. A solution of N-(tertbutyl)methanesulfonamide (14; 3.0 g, 20 mmol ) in THF (20 mL) was added at this temperature under stirring. Then the reaction mixture was slowly warmed up to -30 °C and stirred at this temperature for 30 min, cooled again to -78 °C and at this temperature a solution of 1-acetylindoxyl (13; 3.5 g, 20 mmol) in anhyd THF (50 mL) was quickly added. The mixture was stirred at -78 °C for 30 min, then warmed to 0 °C and poured into a water/ice/concd HCl mixture (300 mL:200 g:20 mL). The product was extracted with EtOAc, the extract was washed with H 2 O, dried, and evaporated. The residue was purified by column chromatography in CHCl 3 -MeOH (9:1). Compound 15 (0.3 g, 5%) was isolated as colorless crystals; mp 192-193°C; R f 0.52 (CHCl 3 -MeOH, 9: 1). 1 H NMR (CDCl 3 ): δ = 8.16 (d, 1 H, J = 7.

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“…The synthesis of one such compound, IMS,2 was first reported by Wieland et al (28) and it was subsequently shown to be biologically active in a variety of test systems (1,10,26,27). Sulfonic acids are considered strong acids with pKa values well below 0 (typically, negative 6.5 [18]) and as such exist essentially fully nonprotonated under physiological conditions.…”

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confidence: 99%

Strongly Acidic Auxin Indole-3-Methanesulfonic Acid

Cohen¹,

Baldi²,

Białek³

1985

Plant Physiol.

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A radiochemical synthesis is described for I"Cqindole-3-methanesulfonic acid (IMS), a strongly acidic auxin analog. Techniques were developed for fractionation and purification of IMS using normal and reverse phase chromatography. In addition, the utility of both Fourier transform infrared spectrometry and fast atom bombardment mass spectrometry for analysis of IMS has been demonstrated. IMS was shown to be an active auxin, stimulating soybean hypocotyl elonption, bean first internode curvature, and ethylene production. IMS uptake by thin sections of soybean hypocotyl was essentially independent of solution pH and, when applied at a 100 micromolar concentration, IMS exhibited a basipetal polarity in its transport in both corn coleoptile and soybean hypocotyl sections. '4C]IMS should, therefore, be a useful compound to study fundamental processes related to the movement of auxins in plant tissues and organelles.

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Natrium‐skatylsulfonat, ein Antagonist von Heteroauxin beim Wurzelwachstum

Abstract: 47X (a-P~enaceiylanzino-~-m~thox~~-propionyl)-S-henxyldzmefh~lc~stern

Cited by 13 publications

References 13 publications

Indole alkaloid sulfonic acids from an aqueous extract of Isatis indigotica roots and their antiviral activity

Indole alkaloid sulfonic acids from an aqueous extract of Isatis indigotica roots and their antiviral activity

Synthesis of (Indol-3-yl)methanesulfonamide and its 5-Methoxy Derivative

Strongly Acidic Auxin Indole-3-Methanesulfonic Acid

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