Synthesis and evaluation of several new (2-chloroethyl)nitrosocarbamates as potential anticancer agents

Academic Article


  • Seven new (2-chloroethyl)nitrosocarbamates have been synthesized as potential anticancer alkylating agents. These compounds were designed with carrier moieties that would either act as prodrugs or confer water solubility. All compounds were screened in an in vitro panel of five human tumor cell lines: CAKI-1 (renal), DLD-1 (colon), NCI-H23 (lung), SK-MEL-28 (melanoma), and SNB-7 (CNS). Several agents showed good activity with IC50 values in the range of 1-10 μg/mL against at least two of the cell lines. One compound, carbamic acid, (2-chloroethyl)nitroso-4-acetoxybenzyl ester (3), was selected for further study in vivo against intraperitoneally implanted P388 murine leukemia. In addition to the aforementioned compound, both carbamic acid, (2-chloroethyl)nitroso-4-nitrobenzyl ester (9) and carbamic acid, (2-chloroethyl)nitroso-2,3,4,6-tetra-O-acetyl-1-α,β-D- glucopyranose ester (24) were evaluated against subcutaneously implanted M5076 murine sarcoma in mice. None of these compounds were active in vivo.
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    Digital Object Identifier (doi)

    Author List

  • Reynolds RC; Tiwari A; Harwell JE; Gordon DG; Garrett BD; Gilbert KS; Schmid SM; Waud WR; Struck RF
  • Start Page

  • 1484
  • End Page

  • 1488
  • Volume

  • 43
  • Issue

  • 8