72552-08-0Relevant articles and documents
(1-Selenocyanatoethyl)benzene: A Selenocyanation Reagent for Site-Selective Selenocyanation of Inert Alkyl C(sp3)-H Bonds
Yu, Fei,Li, Chuang,Wang, Chuangye,Zhang, Hongwei,Cao, Zhong-Yan
supporting information, p. 7156 - 7160 (2021/09/18)
A new, simple, yet easily accessible, (1-selenocyanatoethyl)benzene has been designed and applied as a SeCN group transfer reagent for selenocyanation of aliphatic C(sp3)-H bonds for the first time. This protocol is featured with mild reaction conditions and wide substrate scope. Control experiments reveal that a radical-group transfer mechanism might be involved.
Nucleophilic displacement reactions of 5′-derivatised nucleosides in a vibration ball mill
Eguaogie, Olga,Conlon, Patrick F.,Ravalico, Francesco,Sweet, Jamie S. T.,Elder, Thomas B.,Conway, Louis P.,Lennon, Marc E.,Hodgson, David R. W.,Vyle, Joseph S.
supporting information, p. 87 - 92 (2017/02/15)
Vibration ball-milling in a zirconia-lined vessel afforded clean and quantitative nucleophilic displacement reactions between 4-methoxybenzylthiolate salts and nucleoside 5′-halides or 5′-tosylates in five to 60 minutes. Under these conditions, commonly-e
Accelerated Protein Synthesis via One-Pot Ligation-Deselenization Chemistry
Mitchell, Nicholas J.,Sayers, Jessica,Kulkarni, Sameer S.,Clayton, Daniel,Goldys, Anna M.,Ripoll-Rozada, Jorge,Barbosa Pereira, Pedro José,Chan, Bun,Radom, Leo,Payne, Richard J.
supporting information, p. 703 - 715 (2017/05/15)
Peptide ligation chemistry has revolutionized protein science by facilitating access to synthetic proteins. Here, we describe the development of additive-free ligation-deselenization chemistry at β-selenoaspartate and γ-selenoglutamate that enables the generation of native polypeptide products on unprecedented timescales. The deselenization step is chemoselective in the presence of unprotected selenocysteine, which is highlighted in the synthesis of selenoprotein K. The power of the methodology is also showcased through the synthesis of three tick-derived thrombin-inhibiting proteins, each of which were assembled, purified, and isolated for biological assays within a few hours. The methodology described here should serve as a powerful means of accessing synthetic proteins, including therapeutic leads, in the future.
Tetrazole regioisomers in the development of nitro group-containing antitubercular agents
Karabanovich, Galina,Roh, Jaroslav,Soukup, Ondej,Pvkov, Ivona,Pasdiorov, Markta,Tambor, Vojtch,Stolakov, Jiina,Vejsov, Marcela,Vvrov, Kateina,Klimeov, Vra,Hrablek, Alexandr
supporting information, p. 174 - 181 (2015/02/02)
Tetrazole derivatives containing nitro substituents have been identified as promising antitubercular agents. In this study, the antitubercular potency, selectivity and toxicity of tetrazole 1,5- and 2,5-regioisomers were examined. We prepared a series of 1- and 2-alkyl-5-benzylsulfanyl-2H-tetrazoles and their selenium analogs with various nitro group substitutions. These 1,5- and 2,5-regioisomers were isolated and unambiguously identified using 1H and/or 13C NMR. Among the prepared compounds, 1- and 2-alkyl-5-[(3,5-dinitrobenzyl)sulfanyl]-2H-tetrazole derivatives and their selenium bioisosteres showed the highest antimycobacterial activity, with minimal inhibitory concentration (MIC) values of approximately 1 μM (0.37-0.46 μg mL-1) against Mycobacterium tuberculosis CNCTC My 331/88. The 2-alkyl regioisomers exhibited consistently higher antimycobacterial activity and lower in vitro toxicity against a mammalian cell line compared to the 1-alkyl isomers. The antimycobacterial activity of the 2-alkyl regioisomers was less influenced by the type of alkyl substituent in contrast to 1-alkyl isomers. Furthermore, the 3,5-dinitrobenzyl moiety per se is not the carrier of mutagenicity. These findings encourage further optimization of the 2-alkyl chain to improve the pharmacokinetic properties and toxicity of 2-alkyl-5-[(3,5-dinitrobenzyl)sulfanyl]-2H-tetrazole lead compounds. This journal is
Selenocyanation using a combined reagent of triphenylphosphine and selenocyanogen. A new and simple synthesis of alkyl selenocyanates and symmetrical alkyl diselenides from alcohols
Tamura,Adachi,Kawasaki,Kita
, p. 2251 - 2252 (2007/10/12)
A novel reagent Ph3SeCN)2, easily prepared by adding an equimolar amount of tri-phenylphosphine to selenocyanogen solution in methylene chloride and tetrahydrofuran reacts below -60° with primary alcohols to produce directly the corr
