Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

Moreira, Liliani Salum Alves; Piló‐Veloso, Dorila; Nelson, David Lee

doi:10.1590/s0100-40422000000400003

Cited by 8 publications

(9 citation statements)

References 25 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…In the present case, however, the mass spectra were ambiguous and did not permit a firm assignment of the structures 13 . Therefore, the HMBC, HMQC and TOCSY experiments were performed to verify which groups were bound to the methylene and methine carbons.…”

contrasting

confidence: 70%

“…The observed 13 C-NMR chemical shift values for the product 5 with their proposed assignments (See Fig. 1 for specification of the carbon atom number).…”

mentioning

confidence: 89%

“…tert-butylamine, sec-butylamine and cyclohexylamine), as described elsewhere 13 . The NMR spectra were recorded in DMSO-d 6 at 100 MHz on a Bruker AVANCE DPX 400 spectrometer using TMS as the internal standard.…”

Section: Introductionmentioning

confidence: 99%

“…A user database with the known values obtained from the 13 C-NMR spectra of six 2-(alkylamino)-1-hexanethiosulfuric acids was created ( Table 2). As a result, new chemical shift values could be calculated with greater precision.…”

mentioning

confidence: 99%

See 3 more Smart Citations

Identification of isomers of alkylaminophenylethanethiosulfuric acids by 13C-NMR calculations using a C-13 chemical shift user database and 2D NMR techniques

Moreira¹,

Nelson²,

Binatti³

et al. 1999

J. Braz. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

Na obtenção de ácidos N-alquilaminoalcanotiossulfúricos, existe a possibilidade de formação de dois produtos na última etapa da síntese. No caso dos sete ácidos sintetizados neste laboratório a partir de óxido de estireno e aminas primárias alifáticas, os métodos comuns de espectroscopia não foram adequados para distinguir qual dos dois isômeros foi formado. Cálculos de deslocamentos químicos de carbono-13 empregando o programa ACD/CNMR ajudaram, mas não foram conclusivos para a identificação dos produtos. O uso de técnicas como HMQC, HMBC e TOCSY permitiu a identificação dos produtos como os ácidos 2-(N-alquilamino)-1-phenyl-1-etanotiossulfúricos.In the synthesis of N-alkylaminoalkanethiosulfuric acids, there exists the possibility of forming two products in the last step of the synthesis. In the case of the seven acids synthesized in this laboratory from styrene oxide and primary aliphatic amines, the common spectroscopic methods were inadequate for distinguishing which of the two isomers was obtained. Carbon-13 chemical shift calculations employing the ACD/CNMR program were helpful, but not conclusive for identifying the products. The use of HMQC, HMBC and TOCSY techniques permitted the identification of the products as the 2-(N-alkylamino)-1-phenyl-1-ethanethiosulfuric acids.

show abstract

contrasting

confidence: 70%

“…The observed 13 C-NMR chemical shift values for the product 5 with their proposed assignments (See Fig. 1 for specification of the carbon atom number).…”

mentioning

confidence: 89%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

See 2 more Smart Citations

Identification of isomers of alkylaminophenylethanethiosulfuric acids by 13C-NMR calculations using a C-13 chemical shift user database and 2D NMR techniques

Moreira¹,

Nelson²,

Binatti³

et al. 1999

J. Braz. Chem. Soc.

Self Cite

View full text Add to dashboard Cite

show abstract

“…The compounds studied were synthesized in this laboratory by previously established methods [18][19][20][21] and their structures were established by physical and spectroscopic techniques (infrared, nuclear magnetic resonance and mass spectrometry).…”

Section: Methodsmentioning

confidence: 99%

Reverse Phase Thin Layer Chromatography of Aminoalkanethiosulfuric Acids, Mercaptoalkanamines and Aminoalkyl Disulfides

Cardoso

Nelson

Amaral

et al. 2002

IJMS

View full text Add to dashboard Cite

Abstract:The experimental Rm values for a series of aminoalkanethiosulfuric acids, mercaptoalkanamines and aminoalkyl disulfides were determined by reverse phase thin layer chromatography. The Rm values were determined for various concentrations of methanol:water and the correlation obtained was extrapolated to 100% water. These values permitted the calculation of the log P values for each substance. The log P values obtained by this method were compared with those obtained using the shake-flask method and by theoretical calculations utilizing fragment constants.

show abstract

Antischistosomal activity of aminoalkanethiols, aminoalkanethiosulfuric acids and the corresponding disulfides

Penido¹,

Coelho²,

Mello³

et al. 2008

Acta Tropica

View full text Add to dashboard Cite

Synthesis of 2-(alkylamino)-1-phenylethane-1-thiosulfuric acids, potential schistosomicides

Cited by 8 publications

References 25 publications

Identification of isomers of alkylaminophenylethanethiosulfuric acids by 13C-NMR calculations using a C-13 chemical shift user database and 2D NMR techniques

Identification of isomers of alkylaminophenylethanethiosulfuric acids by 13C-NMR calculations using a C-13 chemical shift user database and 2D NMR techniques

Reverse Phase Thin Layer Chromatography of Aminoalkanethiosulfuric Acids, Mercaptoalkanamines and Aminoalkyl Disulfides

Antischistosomal activity of aminoalkanethiols, aminoalkanethiosulfuric acids and the corresponding disulfides

Contact Info

Product

Resources

About