Isoselenocyanates: A Powerful Tool for the Synthesis of Selenium-Containing Heterocycles

Garud, Dinesh R.; Koketsu, Mamoru; Ishihara, Hideharu

doi:10.3390/12030504

Cited by 101 publications

(31 citation statements)

References 96 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Several modifications30 in the procedure have been made since then to improve yields and avoid polymerization31 of intermediate compounds 29, 32. We have used the method of Fernandez-Bolanos et al 33.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Activity Comparison of Phenylalkyl Isoselenocyanates with Corresponding Naturally Occurring and Synthetic Isothiocyanates

et al. 2008

View full text Add to dashboard Cite

Synthesis and identification of novel phenylalkyl isoselenocyanates (ISCs), isosteric selenium analogs of naturally occurring phenylalkyl isothiocyanates (ITCs), as effective cytotoxic and anti-tumor agents is described. The structure-activity relationship comparison of ISCs with ITCs and effect of the increasing alkyl chain length in inhibiting cancer cell growth was evaluated on melanoma, prostate, breast, glioblastoma, sarcoma, and colon cancer cell lines. IC50 values for ISC compounds were generally lower than their corresponding ITC analogs. Similarly, in UACC 903 human melanoma cells, the inhibition of cell proliferation and induction of apoptosis were more pronounced with ISCs as compared to ITCs. Further, ISCs and ITCs effectively inhibited melanoma tumor growth in mice following intraperitoneal xenograft. A similar reduction in tumor size was observed at three times lower doses of ISCs as compared to corresponding ITCs.

show abstract

Section: Resultsmentioning

confidence: 99%

Synthesis and Anticancer Activity Comparison of Phenylalkyl Isoselenocyanates with Corresponding Naturally Occurring and Synthetic Isothiocyanates

et al. 2008

View full text Add to dashboard Cite

show abstract

“…19 The synthesis and biological evaluation of 5 was very appealing to us since natural products bearing the isoselenocyanate moiety have never been isolated. 20 Furthermore, synthetic isoselenocyanate-containing compounds apparently have never been investigated for potential antiplasmodial or antimycobacterial activity. 21 Thus, insertion of two selenium atom equivalents at C-21 and C-22 of diisocyanide 1 via an isoselenocyanation reaction with Se using TEA in THF at 25 °C led cleanly to 5 (78% yield).…”

mentioning

confidence: 99%

Natural product-based synthesis of novel anti-infective isothiocyanate- and isoselenocyanate-functionalized amphilectane diterpenes

Nieves

Prudhomme

Roch

et al. 2016

Bioorganic & Medicinal Chemistry Letters

View full text Add to dashboard Cite

The marine natural product (−)-8,15-diisocyano-11(20)-amphilectene (1), isolated from the Caribbean sponge Svenzea flava, was used as scaffold to synthetize five new products, all of which were tested against laboratory strains of Plasmodium falciparum and Mycobacterium tuberculosis H37Rv. The scaffold contains two isocyanide units that are amenable to chemical manipulation, enabling them to be elaborated into a small library of sulfur and selenium compounds. Although most of the analogs prepared were less potent than the parent compound, 5 was nearly equipotent showing IC50 values of 0.0066 µM and 0.0025 µM, respectively, against two strains (Dd2 and 3D7) of the malaria parasite. On the other hand, when assayed against the tuberculosis bacterium, analogs 5 and 6 were found to be more potent than 1.

show abstract

“…[15] Although the synthesis of acyclic nucleosides [1b,16] has generated much interest due to their potent biological activities, no selenium-containing acyclic nucleosides have been reported up to now. The chemistry of organoselenium compounds has been developed to a significant small extent because of the intrinsic instability [17] of some of these compounds. We have devoted our efforts in developing strategies to reach, from carbohydrates, stable and versatile organoselenium templates.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the First Selenium‐Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors

et al. 2009

View full text Add to dashboard Cite

We report the synthesis of acyclic and spiranic imidazole-derived C-selenonucleosides. 5-Hydroxy-4-tetrahydroxybutyl imidazolidine-2-selones, a novel class of acyclic selenonucleosides, were transformed into (tetrahydroxybutylimidazol-2-yl)diselenide, by acetylation and chemoselective N-deacetylation with methanolic imidazole. Furthermore, the synthesis of a new class of conformationally restricted arabinoconfigured spironucleosides containing an imidazolidine-2-

show abstract

Isoselenocyanates: A Powerful Tool for the Synthesis of Selenium-Containing Heterocycles

Cited by 101 publications

References 96 publications

Synthesis and Anticancer Activity Comparison of Phenylalkyl Isoselenocyanates with Corresponding Naturally Occurring and Synthetic Isothiocyanates

Synthesis and Anticancer Activity Comparison of Phenylalkyl Isoselenocyanates with Corresponding Naturally Occurring and Synthetic Isothiocyanates

Natural product-based synthesis of novel anti-infective isothiocyanate- and isoselenocyanate-functionalized amphilectane diterpenes

Synthesis of the First Selenium‐Containing Acyclic Nucleosides and Anomeric Spironucleosides from Carbohydrate Precursors

Contact Info

Product

Resources

About