Basic Information
ID: ALA3244088
Journal: J Med Chem
Title: Antitumor agents 32. Synthesis and antitumor activity of cyclopentenone derivatives related to helenalin.
Authors: Lee KH, Mar EC, Okamoto M, Hall IH.
Abstract: Several new cyclopentenones related to helenalin have been synthesized as potential alkylating antitumor agents. The procedure involved the transformation of 2-methyl-2-carbethoxycyclopentanone (2) to an ethylene ketal 3, bromination of 3 followed by dehydrobromination to yield a ketal olefin 5, reduction of 5 to the alcohol 6, conversion of 6 to the corresponding hydroxycyclopentenone 7, and estrification of 7 to afford the cyclopentenone esters 8--11. Biological assays indicated that only cyclopentenones possessing a conjugated ester side chain, such as 9 and 10, demonstrated significant in vitro cytotoxicity against the growth of tissue culture cells originating from human epidermoid carcinoma of the larynx (H.Ep.-2) as well as in vivo antitumor activity in Walker 256 carcinosarcoma in rats and P-388 lymphocytic leukemia in mice.
CiteXplore: 691008
DOI: 10.1021/jm00206a021
Patent ID: ┄
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