1482-82-2Relevant articles and documents
Reactions of selenobenzamide and alkyl halides. Synthesis of dialkyl selenides and diselenides
Zhang, Xiao-Bo,Ruan, Ming-De,Fan, Wei-Qiang
, p. 4665 - 4670 (1996)
In the absence of base, the reaction of selenobenzamide with alkyl halides gives the dialkyl diselenides as the major product. While the reaction of selenobenzamide and an alkyl halide is carried out in a 1:2 molar ratio and in the presence of strong base, the dialkyl selenides predominate.
Chemoselective synthesis of fuctionalized diselenides
Salama,Bernard
, p. 5711 - 5714 (1995)
The action of LiEt3BH or DIBAL-H on various functionalized selenocyanates was proven to be an efficient means to establish chemoselectively the diselenide bond, under very mild conditions. The mechanism was shown to involve a selenophilic hydri
A convenient one-pot synthesis of dibenzyl diselenides under microwave irradiation conditions
Wang, Jin-Xian,Bai, Lin,Li, Wenbo,Hu, Yulai
, p. 325 - 332 (2000)
A simple, rapid and efficient method for the synthesis of dibenzyl diselenides under microwave irradiation is reported. The effect of microwave irradiation power, times and solvent on the reaction is investigated.
An efficient and practical method for the selective synthesis of sodium diselenide and diorganyl diselenides through selenium reduction
Lim, Yoo Jin,Shin, Na Hye,Kim, Chorong,Kim, Ye Eun,Cho, Hyunsung,Park, Myung-Sook,Lee, Sang Hyup
, (2020)
Studies on an efficient and practical method for the selective synthesis of diorganyl diselenides over diorganyl selenides are presented. Considering the discrepancies between reports on organoselenium compounds, we wanted to establish a tolerable synthetic method for diorganyl diselenides and investigate their characteristics. We optimized reaction conditions for sodium diselenide preparation using selenium, NH2NH2·H2O, and NaOH and, by treating the obtained sodium diselenide with various alkyl or aryl halides, achieved the selective synthesis of diorganyl diselenides in modest to good yields (57–88%) with good reproducibility. We further studied the mechanistic implication, the effects of solvent changes, and the stability of diorganyl diselenides.
A synthetic method for diselenides under phase-transfer conditions
Hu, Xubo,Tian, Zhenjiao,Lu, Xueran,Chen, Yuanyin
, p. 553 - 557 (1997)
Diselenides were easily prepared in high yields by the alkylation of sodium diselenide on halides in water under phase-transfer conditions.
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 (1979)
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
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Lewicki,J.W. et al.
, p. 552 (1976)
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Chu et al.
, p. 4905 (1975)
The Convenient Syntheses of Organoselenium Reagents
Syper, Ludwig,Mlochowski, Jacek
, p. 439 - 442 (1984)
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Lead optimization generates selenium-containing miconazole CYP51 inhibitors with improved pharmacological profile for the treatment of fungal infections
Xu, Hang,Yan, Zhong-zuo,Guo, Meng-bi,An, Ran,Wang, Xin,Zhang, Rui,Mou, Yan-hua,Hou, Zhuang,Guo, Chun
, (2021/03/16)
A series of selenium-containing miconazole derivatives were identified as potent antifungal drugs in our previous study. Representative compound A03 (MIC = 0.01 μg/mL against C.alb. 5314) proved efficacious in inhibiting the growth of fungal pathogens. However, further study showed lead compound A03 exhibited potential hemolysis, significant cytotoxic effect and unfavorable metabolic stability and was therefore modified to overcome these drawbacks. In this article, the further optimization of selenium-containing miconazole derivatives resulted in the discovery of similarly potent compound B17 (MIC = 0.02 μg/mL against C.alb. 5314), exhibiting a superior pharmacological profile with decreased rate of metabolism, cytotoxic effect and hemolysis. Furthermore, compound B17 showed fungicidal activity against Candida albicans and significant effects on the treatment of resistant Candida albicans infections. Meanwhile, compound B17 not only could reduce the ergosterol biosynthesis pathway by inhibiting CYP51, but also inhibited biofilm formation. More importantly, compound B17 also shows promising in vivo efficacy after intraperitoneal injection and the PK study of compound B17 was evaluated. In addition, molecular docking studies provide a model for the interaction between the compound B17 and the CYP51 protein. Overall, we believe that these selenium-containing miconazole compounds can be further developed for the potential treatment of fungal infections.
Synthesis of unsymmetrical glycosyl diselenides by the treatment of symmetrical diselenides with glycosyl selenocyanates
Manna, Tapasi,Misra, Anup Kumar,Rana, Abhijit
, (2021/08/03)
A novel reaction condition has been developed for the synthesis of unsymmetrical glycosyl diselenide derivatives in excellent yield by the reaction of glycosyl selenocyanates as selenol surrogates with symmetrical diselenides in the presence of hydrazine monohydrate at room temperature. The reaction metal-free condition is reasonably fast, simple, non-malodorous and suitable for scale-up.
Synthesis of Dibenzylic Diselenides from Elemental Selenium and Benzylic Quaternary Ammonium Salts
Chen, Feng,Li, Fuhai,Zeng, Qingle
, p. 5605 - 5608 (2021/11/11)
Abstract: Substituted dibenzyl diselenides are synthesized in good yields (74–91 %) by SN2 nucleophilic substitution of benzylic trimethylammonium salts and diselenide dianion (Se2?), in situ generated from elemental selenium, under
