Carbonimidic dichlorides

That farnesyl isothiocyanate (130), and not the corresponding isocyano compound, was isolated together with several carbonimidic dichlorides (structures not shown) suggested a possible biosynthetic relationship among the nitrogenous functions [60]. 

Kehraus S, Konig GM, Wright AD (2001) New Carbonimidic Dichlorides from the Australian Sponge Ulosa spongia and Their Possible Taxonomic Significance. J Nat Prod 64 939... 

Musman M, Tanaka J, Higa T (2001) New Sesquiterpene Carbonimidic Dichlorides and Related Compounds from the Sponge Stylotella aurantium. J Nat Prod 64 111... 

Brust A, Garson MJ (2004) Dereplication of Complex Natural Product Mixtures by 2D NMR Isolation of a New Carbonimidic Dichloride of Biosynthetic Interest from the Tropical Marine Sponge Stylotella aurantium. ACGC Chem Res Commun 17 33... 

Tanaka J, Higa T (1999) Two New Cytotoxic Carbonimidic Dichlorides from the Nudibranch Reticulida fungia. J Nat Prod 62 1339... 

A second group of bioactive sponge metabolites with an unusual structural motif are the terpene isocyanides, which often co-occur with structurally related isothiocyanates and forma-mides.157-159 Less commonly encountered nitrogenous based substituents present in sponge terpene metabolites include isocyanates, thiocyanates, and dichloroimines (carbonimidic dichlorides). The biochemistry and ecology of these unique marine metabolites have been targeted for study by numerous researchers.159 160... 

N-piCHLOROMETHYLENE)ANILINE PHENYL-CARBONIMIDIC DICHLORIDE N-PHEN XCARBO-NIiMIDIC DICHLORIDE PHENYL CARBYLAMINE CHLORIDE PHENYLCARBYLAMINE CHLORIDE POTI PHENYLIMIDOCARBONYL CHLORIDE N-PHENYLIMIDOPHOSGENE PHENYLIMINO-CARBONYL DICHLORIDE N-PHENYLIMINO-CARBONYL DICHLORIDE PHENYLISONITRILE DICHLORIDE... 

CARBONIC ANHYDRIDE see CBU250 CARBONIC DIFLUORIDE see CCA500 CARBONIC DIHYDRAZIDE see CBS500 CARBONIC OXIDE see CBW750 CARBONIMIDIC DICHLORIDE, PHENYL-(9CI) see PFJ400... 

Interest in the metabolites of marine organisms remains undiminished (see, e.g. Vol. 8, pp. 65,66,75,79,82,101,108). A detailed investigation of the terpenoid constituents of the Indo-Pacific sponge Pseudaxinyssa pitys) has resulted in the isolation of several novel carbonimidic dichlorides (38)—(42). It has been... 

Compared to isocyanides and isothiocyanates, there are far fewer examples of thiocyanate (135-139), dichloroimine (= carbonimidic dichlorides 140-146), isocyanate (36, 60, 70, 71) or amine (61,63, 65-67) groups in the marine terpene literature. The isocyanates which have been isolated [18-21] are shown in Table 1 or 2 respectively because these unusually-functionalised compounds are generally isolated together with the corresponding isocyanides or isothiocyanates, however most sesquiterpene thiocyanates (e.g. (135) [8]) represent a unique structural classes for which no isocyanide or isothiocyanate representative has yet been isolated, and these are therefore listed separately in Table 3. To date, 2-thiocyanatopupukeanane (139) [10] is the only example of a thiocyanate whose carbon skeleton has also been isolated with an isocyanide substituent 2-isothiocyanatopupukeanane is a known metabolite but has not been formally characterised in the literature. Dichloroimines such as stylotellanes A and B (141) and (140) have been found in sponges together with farnesyl isothiocyanate (147), but as yet not with any isocyanides [14-17], while very few ureas and thioureas have been isolated [23, 25, 26]. For convenience, we have therefore shown separately a list of all reported isolations of thiocyanates, dichloroimines, ureas and thioureas by structural class (Table 3). 

Wratten, S.J. and Faulkner, D.J., 1977. Carbonimidic dichlorides from the marine sponge Pseudaxinyssa pitys. J. Am. Chem. Soc., 99 7367—7368. 

Several carbonimidic dichlorides, such as 144, have been isolated from marine sources h252 xhese compounds unlike their corresponding isonitriles were not biologically active, and the latter may be chlorinated in vivo to give protected compounds that could be readily unmasked to give the active species when needed. 

Musman, M., Tanaka, J., and Higa, T. (2001a) New sesquiterpene carbonimidic dichlorides and related compoimds from the sponge Stylotella aurantium. J. Nat. Prod., 64,111-113. 

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