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Abstract
The reaction of 3-aminopropylamide of cholic acid with CS2 produced a bile acid derivative of dithiocarbamic acid which further formed an ammonium salt with another molecule of 3-aminopropylamide of cholic acid. The cationic 3-ammonium propylamide of cholic acid did not react further with CS2 and the formed salt was stable in the reaction mixture, even when excess CS2 was used. When the reaction was carried out in the presence of aqueous sodium hydroxide, only the bile acid derivative of sodium dithiocarbamate was formed. The dithiocarbamate derivatives were characterized by 1H- and 13C-NMR spectroscopy and ESI-TOF mass spectrometry.
Highlights
It is known that amines react with CS2 forming dithiocarbamates [1,2,3,4,5,6]
As a biologically important expansion of the topic, we present the synthesis and characterization of cholic acid-derived ammonium dithiocarbamates
Spectra of the sodium dithiocarbamate derivative of cholic acid 3-aminopropylamide was used to distinguish the assignments of anionic and cationic parts.1H-NMR spectral assignments of nonsteroidal parts and some of the steroidal part are presented in Figure 2, where the signals marked in blue coming from the cationic part and those marked in red from the anionic part, respectively
Summary
It is known that amines react with CS2 forming dithiocarbamates [1,2,3,4,5,6]. Recently, Yavari et al [7]. Dithiocarbamates exhibit numerous biological activities [9,10,11,12] and they are used in agriculture [12,13,14] and as linkers in solid-phase organic synthesis [15,16,17]. As a biologically important expansion of the topic, we present the synthesis and characterization of cholic acid-derived ammonium dithiocarbamates. This straightforward synthetic method offers an effective route to bile acid derivatives with increased water solubility, which is an essential property in Molecules 2011, 16 the design of physiologically active receptors [20,21] and drug carriers [22]. The synthetic route and numbering of 2 are shown in Scheme 1
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