-transparent.png){kind=logo}
The C-9 and C-7 monoesters and C-7, C-9 diesters of heliotridine with (S)-(+) and (R)-(-)-2-hydroxy-2-phenylbutyric acid were prepared, converted into their N-oxides, and compared with the corresponding C-9 monoesters of retronecine in the in vivo P388 lymphocytic leukemia screen. Relative in vitro cytotoxicities of some of the free bases and their corresponding N-oxides were also measured against the A204 rhabdomyosarcoma cell line by using the soft agar colony forming assay. Stereochemistry at C-7 of the necine and at C-2' of the necine acid appears to have a significant effect on the antitumor activity in this system. In the heliotridine series, the configuration of the necic acid has a pronounced effect on the site selectivity (C-7 vs C-9) in esterification with carbodiimidazole. An explanation for this site selectivity is offered.
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
January 1977,
Journal of the Chemical Society. Perkin transactions 1,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
May 1987,
Cancer treatment reports,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
November 1979,
Cancer research,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
May 2008,
Toxicology letters,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
January 2006,
Cancer letters,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
October 2017,
Journal of food and drug analysis,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
July 1970,
Molecular pharmacology,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
January 1976,
Indian journal of experimental biology,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
December 2017,
Archives of toxicology,
L H Zalkow, and
J A Glinski, and
L T Gelbaum, and
D Moore, and
D Melder, and
G Powis
January 1971,
Xenobiotica; the fate of foreign compounds in biological systems,
