- Anti-nitric oxide production activity of isothiocyanates correlates with their polar surface area rather than their lipophilicity
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There is increasing demand for novel anti-inflammatory drugs with different mechanisms of action. We synthesized a series of isothiocyanates 2b-h based on 6-(methylsulfinyl)hexyl isothiocyanate (6-MITC) found in the pungent spice Wasabia japonica. Inhibit
- Noshita, Toshiro,Kidachi, Yumi,Funayama, Hirokazu,Kiyota, Hiromasa,Yamaguchi, Hideaki,Ryoyama, Kazuo
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- Structure-Activity Relationship Study on Isothiocyanates: Comparison of TRPA1-Activating Ability between Allyl Isothiocyanate and Specific Flavor Components of Wasabi, Horseradish, and White Mustard
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Allyl isothiocyanate (ITC) (4) is the main pungent component in wasabi, and it generates an acrid sensation by activating TRPA1. The flavor and pungency of ITCs vary depending on the compound. However, the differences in activity to activate TRPA1 between ITCs are not known except for a few compounds. To investigate the effect of carbon chain length and substituents of ITCs, the TRPA1-activiting ability of 16 ITCs was measured. Since most of the ITCs showed nearly equal TRPA1-activiting potency, the ITC moiety is likely the predominant contributor to their TRPA1-activating abilities, and contributions of other functional groups to their activities to activate TRPA1 are comparatively small. (Figure Presented).
- Terada, Yuko,Masuda, Hideki,Watanabe, Tatsuo
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p. 1937 - 1941
(2015/09/08)
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- Staudinger condensation for the preparation of thiohydantoins
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An efficient one-pot, two-step sequence starting from azide derivatives is described: first, formation of iminophosphoranes (Staudinger reaction) and condensation with carbon disulfide to form nonisolated isothiocyanates; then, condensation with α-amino e
- Gosling, Sandrine,El Amri, Chahrazade,Tatibouet, Arnaud
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p. 1079 - 1084
(2014/05/06)
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- BIOTRANSFORMATION OF ORGANIC SULFIDES. PART 7. FORMATION OF CHIRAL ISOTHIOCYANATO SULFOXIDES AND RELATED COMPOUNDS BY MICROBIAL BIOTRANSFORMATION
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The fungi Helminthosporium species NRRL 4671 and Mortierella isabellina ATCC 42613 have been used for the biotransformation of a series of isothiocyanatoalkyl methyl sulfides and their synthetic precursors, ω-(methylthio)alkylphthalimides.H. species gave predominantly (S) sulfoxides in all cases; M. isabellina gave (R) isothiocyanatoalkyl methyl sulfoxides, but in the case of two ω-(methylthio)alkylphthalimides substantial conversion of sulfoxide to sulfone resulted in the isolation of the former with predominant (S) configuration.A correction is made of the previously reported configurations of two biotransformation products (Tetrahedron: Asymmetry, 1994, 5, 1129).
- Holland, Herbert L.,Brown, Frances M.,Larsen, Brett G.,Zabic, Mirjana
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p. 1569 - 1574
(2007/10/02)
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