Isothiocyanates compounds

Other reagents used for fluorescence derivatization are the so-called Edman-type isothiocyanate compounds, namely fluoresceinisothiocyanate (163), 9-isothi-ocyanatoacridine (164), 4-dimethylamino-l-naphthylisothiocyanate (165), or... 

The marine isothiocyanates, with more than 80 compounds isolated so far, form the largest group of naturally occurring isothiocyanates. This well-established group of marine natural products is constituted mainly by terpene metabolites present as sesquiterpene and diterpene derivatives. The non-terpene isothiocyanate compounds include two cylindricine alkaloids and a series of long-chain aliphatic metabolites. Marine sponges constitute the main source of these compounds, although they are also found in nudibranches and tunicates. 

Isothiocyanate compounds react best at alkaline pH values where the target amine groups are mainly unprotonated. Many reactions are done on 0.1M sodium carbonate buffer at pH 9. Reaction times vary from 4 to 24 h at 4°C. Since the isothiocyanate group is relatively unstable in aqueous conditions, reagents containing this function should be stored desiccated at refrigerator or freezer temperatures. 

Riggs JL, Seiwald RJ, Burckhalter JH, Downs CM, Metcalf TG (1958) Isothiocyanate compounds as fluorescent labeling agents for immune semm. Amer J Path 34 1081. 

In addition to isothiocyanates, compounds having the configuration RN=C(SX)2 (X = alkyl or K) react rapidly with chlorine to produce carbonimidoyl dichlorides. Thus, Neidlein and his co-workers and Gompper and Kunz ( )obtained arylsulfonylcarbonimidoyl dichlorides X in the reaction of S,S-dialkyl-N-sulfonyldithiocarbonimides XI with chlorine. 

Trifluoroacetyl derivatives were prepared by treating the isothiocyanate compounds in EtOAc with a few drops of trifluoroacetic anhydride and allowing the solution to stand at room temperature for 30 min. 

Khor, TO. et aL (2006) Pharmacogenomics of cancer chemopreventive isothiocyanate compound sulforaphane in the intestinal polyps of ApcMin/ + mice. Biopharm Drug Dispos 27 (9), 407-420... 

Rather than include this section in the previous chapter, it was felt that it would best be treated here together with isothiocyanate compounds.)... 

Adamantylthioureas, which exhibit marked antiviral activity, are obtained from 1-aminoadamantane and isothiocyanates. Compound (11) is similarly obtained from 4-aminophenyl phosphate. Oxazolyl-2-thioureas (12) are only obtained as minor products from 2-amino-oxazoles, the main components of the reaction mixture being the thioamides (13 R = Me, Et, allyl, or Ph). ... 

Scheme 16 Reactivities of [(6)YI] and [(6)Y(CH2Ph)] toward a isothiocyanate compound...

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