116505-53-4Relevant academic research and scientific papers
Hypoxia-Selective Antitumor Agents. 11. Chlorambucil N-Oxide: A Reappraisal of Its Synthesis, Stability, and Selective Toxicity for Hypoxic Cells
Tercel, Moana,Wilson, William R.,Denny, William A.
, p. 1247 - 1252 (1995)
The potential hypoxia-selective cytotoxin 4-phenyl>butanoic acid N-oxide (chlorambucil N-oxide, 4) was synthesized and characterized as its hydrochloride salt.This compound was shown to be unstable, decomposing in some organic solvents to the hydroxylamine 4-phenyl>butanoic acid (11) by a mechanism previously demonstrated for aliphatic mustard N-oxides and under aqueous conditions to a more complex mixture, of which the predominant components were the monochloroethyl derivative 7 and formaldehyde.Comparison of NMR spectra showed that a recent published synthesis of 4 in fact resulted in the rearrangement product 11, indicating that recent reported investigations of the hypoxia-selective cytotoxicity and metabolism of chlorambucil N-oxide have examined this rearrangement product rather than 4.In a clonogenic assay, 4 was less cytotoxic against AA8 cells than was chlorambucil, but the effect of oxygen on cytotoxicity was no greater than for chlorambucil itself.
COMPOUNDS AND METHODS USEFUL FOR TREATMENT OF DISEASES MEDIATED BY HIF-1
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Page/Page column 77, (2012/05/19)
Provided herein are compounds that are useful in treatment of diseases mediated by HIF-1.
