21871-47-6Relevant articles and documents
5-(Benzylmercapto)-1H-tetrazole as activator for 2′-O-TBDMS phosphoramidite building blocks in RNA synthesis
Welz, Rüdiger,Müller, Sabine
, p. 795 - 797 (2002)
An improved method for the preparation of 5-(benzylmercapto)-1H-tetrazol as activator in RNA synthesis is described. Reaction of benzylthiocyanate with azide delivers the corresponding tetrazole with 72% yield under optimised conditions. We demonstrate that 5-(benzylmercapto)-1H-tetrazol is a superior activator of 2′-O-TBDMS phosphoramidite building blocks. Compared to routinely used 1H-tetrazol, application of a 0.25 M 5-(benzylmercapto)-1H-tetrazol solution in acetonitrile allows for higher coupling yields (>99%), lower coupling times (3 min) and reduced excess of phosphoramidites in solution over the solid-phase nucleotides (8-fold).
L -Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1 H -Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide
Bhagat, Saket B.,Telvekar, Vikas N.
supporting information, p. 874 - 879 (2018/02/16)
A simple and efficient route for the synthesis of a series of 5-substituted 1 H -tetrazoles using l -proline as a catalyst from structurally diverse organic nitriles and sodium azide is reported. The prominent features of this environmentally benign, cost effective, and high-yielding l -proline-catalyzed protocol includes simple experimental procedure, short reaction time, simple workup, and excellent yields making it a safer and economical alternative to hazardous Lewis acid catalyzed methods. The protocol was successfully applied to a broad range of substrates, including aliphatic and aryl nitriles, organic thiocyanates, and cyanamides.
Synthesis and antibacterial evaluation of new sulfanyltetrazole derivatives bearing piperidine dithiocarbamate moiety
Baghershiroudi, Mahrokh,Safa, Kazem D.,Adibkia, Khosro,Lotfipour, Farzaneh
, p. 323 - 328 (2018/02/09)
A series of new alkyl or aryl sulfanyltetrazole derivatives containing dithiocarbamate moiety (5a–6e) were synthesized. The structures of the compounds were characterized by IR, 1H NMR, 13C NMR spectra, and elemental analysis data. The present study examines the antibacterial potential of novel synthetic sulfanyltetrazole compounds against clinically important gram-positive and -negative strains. The results of screening showed that attachment of dithiocarbamate to sulfanyltetrazole derivatives results in enhancement of antibacterial activity. The compound 6d showed the best activity among the tested compounds. Also, the less polar 2,5-disubstituted sulfanyltetrazole regioisomers showed an increased antibacterial activity compared with the corresponding more polar regioisomers.
Bulky organosilicon compounds based on sulfanyltetrazoles: their synthesis and in vitro antibacterial evaluation
Baghershiroudi, Mahrokh,Safa, Kazem D.,Adibkia, Khosro,Lotfipour, Farzaneh
, p. 1279 - 1286 (2018/05/22)
The study introduces different organosilicon derivatives incorporating sulfanyltetrazole ring for biological applications. Initially, the sulfanyltetrazole derivatives and halo-analogues (Br, I) were synthesized. Later, selective reaction of tris(trimethylsilyl)methyllithium (TsiLi) in the presence (?46 and 0?°C) and absence (room temperature) of CS2 with halo-sulfanyltetrazole derivatives yielded new multifunctional sulfanyltetrazole regioisomers with SH, C?=?S, ethynylthio and SiMe3 groups, respectively. All the synthesized compounds were characterized by IR, 1H-NMR, 13C-NMR spectra and elemental analysis data. The compounds were screened for their antibacterial activities against clinically important gram-positive and gram-negative bacteria using the spectrophotometric microdilution method. The preliminary screening indicated that the organosilicon derivatives incorporating SH and C?=?S (mercapto-silyl-thiones) and silyl-thioalkynes have antibacterial activities, whereas no antibacterial activity was observed on compounds containing (Me3Si)3C groups. Of the synthesized compounds, compound 5d showed the best activity against all the tested organisms (3.91–31.25?μg/mL).
