Cyclophosphamide analogues

Tsoupras et al. used 31p nmr to detect the presence of phosphate groups in the 22-adenosinemonophosphoric ester of 2-deoxy-ecdysone and 22-phospho-2-deoxyecdysone (34). Quantitative NMR has been used in several studies. Wayne et al. used 51p nmr for quantitative analysis of organophosphorous pesticides (35). Zon et al. used NW to study chemical and microsomal oxidation of cyclophosphamide ( ), and to determine the half-life of a cyclophosphamide analogue (37). 

New derivatives and analogues of cyclophosphamide (35 R = H) have been reported80 and the diastereoisomeric jY-l-phenylethyl derivatives (35 ... 

Alkyl halides, alkyl sulfonates and other alkylating agents have also been subject to scmtiny in spheres other than pharmaceuticals, such as in environmental analysis. Various approaches have included two-step SPE, derivatisation with trifluoroacetic anhydride followed by GC/MS (for cyclophosphamide and its analogues in sewage water) SPE on surface water to isolate the antineoplastic agents carmustine, chlorambucil, cyclophosphamide and melphalan for LC-UV and LC-fluorescence measurements and derivatisation of alkyl halides and epoxides with 4-nitrothiophenol followed by HPLC-UV detection (claimed to be better than NBP derivatisation). A patent exists for a field test kit for mustard gases in military use based on NBP derivatisation. 

The nitrogen mustard analogues are nitrogen derivatives of sulfur mustard, used as poison gas in World War I. Agents include cyclophosphamide, mechlorethamine, chlorambucil, melphalan, ifos-famide, uramustine and estramustine. 

Ifosfamide (Ifex) is an analogue of cyclophosphamide that requires metabolic activation to form 4-hydroxy-ifosfamide. In general, the metabolism, serum half-life, and excretion of ifosfamide are similar to those of cyclophosphamide. 

Fleer R, Brendel M. 1982. Toxicity, interstrand cross-links and DNA fragmentation induced by activated cyclophosphamide in yeast Comparative studies on 4-hydroxyperoxy-cyclophosphamide, its monofunctional analogue, acrolein, phosphoramide mustard, and nor-nitrogen mustard. Chem Biol Interact 39 1-15. 

Electrochemical oxidation of anticancer drugs ifosfamide and cyclophosphamide produced in high yield methoxylated analogues of the key hydroxy-metabolites of these oxazaphosphorine prodrugs (Scheme 19). ... 

Steroid hormone analogues [e.g. (471)] carrying the cyclophosphamide system have been synthesized as potential anti-tumour agents. ... 

Numerous reports of the synthesis of cyclic analogues have appeared. The cyclophosphamidic chloride 2 has been prepared as a single enantiomer and... 

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