103-72-0Relevant articles and documents
Isothiocyanates from tosyl chloride mediated decomposition of in situ generated dithiocarbamic acid salts
Wong, Rince,Dolman, Sarah J.
, p. 3969 - 3971 (2007)
(Chemical Equation Presented) A facile and general protocol for the preparation of isothiocyanates from alkyl and aryl amines is reported. This method relies on a tosyl chloride mediated decomposition of a dithiocarbamate salt that is generated in situ by treatment of an amine with carbon disulfide and triethylamine. Utilizing this protocol, we have prepared 19-alkyl- and arylisothiocyanates in moderate to excellent yield.
Triphosgene: An efficient catalyst for synthesis of isothiocyanates
Chaskar,Yewale,Bhagat,Langi
, p. 1972 - 1975 (2008)
Isothiocyanates are bioactive molecules that show various biological activities such as antifungal and anathematic activities. They play a vital role in the synthesis of various heterocyclic compounds. Various isothiocyanates were prepared in good to high yield using triphosgene. Copyright Taylor & Francis Group, LLC.
Inhibitors of the Diadenosine Tetraphosphate Phosphorylase Rv2613c of Mycobacterium tuberculosis
G?tz, Kathrin H.,Hacker, Stephan M.,Mayer, Daniel,Dürig, Jan-Niklas,Stenger, Steffen,Marx, Andreas
, p. 2682 - 2689 (2017)
The intracellular concentration of diadenosine tetraphospate (Ap4A) increases upon exposure to stress conditions. Despite being discovered over 50 years ago, the cellular functions of Ap4A are still enigmatic. If and how the varied Ap4A is a signal and involved in the signaling pathways leading to an appropriate cellular response remain to be discovered. Because the turnover of Ap4A by Ap4A cleaving enzymes is rapid, small molecule inhibitors for these enzymes would provide tools for the more detailed study of the role of Ap4A. Here, we describe the development of a high-throughput screening assay based on a fluorogenic Ap4A substrate for the identification and optimization of small molecule inhibitors for Ap4A cleaving enzymes. As proof-of-concept we screened a library of over 42, 000 compounds toward their inhibitory activity against the Ap4A phosphorylase (Rv2613c) of Mycobacterium tuberculosis (Mtb). A sulfanylacrylonitril derivative with an IC50 of 260 ± 50 nM in vitro was identified. Multiple derivatives were synthesized to further optimize their properties with respect to their in vitro IC50 values and their cytotoxicity against human cells (HeLa). In addition, we selected two hits to study their antimycobacterial activity against virulent Mtb to show that they might be candidates for further development of antimycobacterial agents against multidrug-resistant Mtb.
Dynamic Ureas with Fast and pH-Independent Hydrolytic Kinetics
Cai, Kaimin,Ying, Hanze,Cheng, Jianjun
, p. 7345 - 7348 (2018)
Low cost, high performance hydrolysable polymers are of great importance in biomedical applications and materials industries. While many applications require materials to have a degradation profile insensitive to external pH to achieve consistent release profiles under varying conditions, hydrolysable chemistry techniques developed so far have pH-dependent hydrolytic kinetics. This work reports the design and synthesis of a new type of hydrolysable polymer that has identical hydrolysis kinetics from pH 3 to 11. The unprecedented pH independent hydrolytic kinetics of the aryl ureas were shown to be related to the dynamic bond dissociation controlled hydrolysis mechanism; the resulting hindered poly(aryl urea) can be degraded with a hydrolysis half-life of 10 min in solution. More importantly, these fast degradable hindered aromatic polyureas can be easily prepared by addition polymerization from commercially available monomers and are resistant to hydrolysis in solid form for months under ambient storage conditions. The combined features of good stability in solid state and fast hydrolysis at various pH values is unprecedented in polyurea material, and will have implications for materials design and applications, such as sacrificial coatings and biomaterials.
A convenient synthesis of isothiocyanates from nitrile oxides
Kim, Jae Nyoung,Ryu, Eung K.
, p. 8283 - 8284 (1993)
Isothiocyanats were prepared in quantitative yields from the reaction of nitrile oxides with thiourea in tetrahydrofuran at room temperature in short time.
A metal-free synthesis of 2-aminobenzothiazoles through aminyl radical addition to aryl isothiocyanates
He, Yimiao,Li, Jing,Luo, Shuang,Huang, Jinbo,Zhu, Qiang
, p. 8444 - 8447 (2016)
A convenient synthesis of 2-aminobenzothiazoles, starting from aryl isothiocyanates and formamides under metal-free conditions, is described. Various secondary and tertiary amine- and even α-amino acid-derived formamides can be used as amino sources in this process. Mechanistic studies suggest that the reaction is initiated by decarbonylative aminyl radical formation in the presence of n-Bu4NI and TBHP, followed by aminyl radical addition to isothiocyanates and cyclization via sulfur centred radical intermediates.
Synthesis of Multifunctional 2-Aminobenzimidazoles on DNA via Iodine-Promoted Cyclization
Fan, Jing,Feng, Jing,Franklin, G. Joseph,Lancia, David R.,Li, Jin,Liu, Guansai,O'connell, Jonathan,Peng, Ting,Su, Liqiang,Wan, Jinqiao
, (2020)
2-Aminobenzimidazole cores are among the most common structural components in medicinal chemistry and can be found in many biologically active molecules. Herein, we report a mild protocol for the synthesis of multifunctional 2-aminobenzimidazoles on-DNA with broad substrate scopes. The reaction conditions expand our ability to design and synthesize 2-aminobenzimidazole core-focused DNA-encoded libraries.
Novel selenium catalyzed synthesis of isothiocyanates from isocyanides and elemental sulfur
Fujiwara, Shin-Ichi,Shin-Ike, Tsutomu,Sonoda, Noboru,Aoki, Minoru,Okada, Kazuhiro,Miyoshi, Noritaka,Kambe, Nobuaki
, p. 3503 - 3506 (1991)
A variety of aliphatic and aromatic isothiocyanates were synthesized in good to excellent yields from corresponding isocyanides and elemental sulfur under mild conditions by use of catalytic amounts of elemental selenium.
Synthesis of isothiocyanates by reaction of amides with carbon disulfide in the presence of solid potassium carbonate/sodium hydroxide mixture
Albanese,Penso
, p. 1001 - 1002 (1991)
Readily available N-monosubstituted trifluoroacetamides are transformed into isothiocyanates in good yield by reaction, at room temperature, with carbon disulfide in acetonitrile in the presence of anhydrous sodium hydroxide/potassium carbonate basic mixture.
Molecular iodine mediated preparation of isothiocyanates from dithiocarbamic acid salts
Nath, Jayashree,Ghosh, Harisadhan,Yella, Mamesh,Patel, Bhisma K.
, p. 1849 - 1851 (2009)
We have developed a general economical and environmentally benign method for the preparation of isothiocyanates from the corresponding dilhiocarbamic acid salts by using cheap and readily available reagent molecular iodine. This is perhaps the most efficient method reported so far for the synthesis of isothiocyanates. The reagent is easily available and nontoxic, and the precipitated sulfur can be removed easily; hence, this method is most suitable for large-scale synthesis. Wiley-VCH Verlag GmbH & Co. KGaA.
