Halogenated analogues

Infante PF, Tsongas TA. 1982. Mutagenic and oncogenic effects of chloromethanes, chloroethanes, and halogenated analogues of vinyl chloride. Environmental Science Research 25 301-327. 

It was concluded from these results that the halogenated analogues of triphenyl-methyl and further triphenylmethyl itself in some way must have a chinoid constitution. 

Unlike mebendazole, flubendazole which is its halogenated analogue, produces only one-tenth of the plasma levels attained with mebendazole. When swine or poultry are treated with flubendazole, the tissue with the highest residues concentration and the slowest depletion rate is the liver. Residues in swine liver are primarily composed of the (2-amino-lH-benzimidazol-5-yl)-4-fluorophenyl-methanone metabolite, which is generally found at a much higher concentration than die parent drug. 

A large number of halogenated analogues are among the multitudinous synthetic nucleosides and nucleotides that have been prepared in the search for effective antiviral and antitumor agents. A comprehensive survey of this field is beyond the scope of this chapter. Selected examples will be given with an emphasis on the biochemical rationales involved. 

Toxic affects of 2-fluoro-L-histidine (2-FHis) (98) on bacteria have been attributed in part to the action of this analogue as a potent feed back inhibitor of ATPiphosphoribo-syl transferase, the first committed enzyme in histidine biosynthesis. No other halogenated analogues of histidine were active in this regard155. 

Calculated values of the band gaps E and band widths BW for (-CH-CH) and some halogenated analogues, all in the trans ( - 0 ) conformation, are presented in Table II. 

Chloromethanes and halogenated analogues of vinyl chloride. Environmental Science Research 25 301-327. 

Important classes of nonionic surfactants are aliphatic poly-ethoxylate alcohols (AEO), and octyl or nonyl phenol polyethoxylates (OPEO and NPEO). The alkylphenol ethoxylates (APEO) attracted special attention due to their supposedly endocrine disrupting properties (Ch. 8.3). LC-MS analysis may also involve nonylphenolethoxycarboxylates (NPEC), biodegradation products of NPEO, and halogenated analogues, generated in chlorine disinfection treatments in drinking water production plants. 

The inactivation of Ala-R by trihaiogenated alanine analogues is shown in Figure 38. According to the mechanism proposed by Faraci and Walsh,the addition of the halogenated analogue leads to an initial transaldimination, followed by the elimination of the first fluoride ion and formation of the /3-difluoro-a,/3-unsaturated imine complex. The subsequent nucleophilic attack of the enzyme on the olefinic terminus induces the loss of the second fluoride ion and the formation of a stable inactive complex." ... 

---