Stereoselective effects of cis- and trans-cyclopropylbis(dioxopiperazines) related to ICRF-159 on metastases of a hamster lung adenocarcinoma
- 1 December 1978
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of Medicinal Chemistry
- Vol. 21 (12) , 1194-1197
- https://doi.org/10.1021/jm00210a004
Abstract
The synthesis for cis-4,4''-(1,2-cyclopropanediyl)bis(2,6-piperazinedione) (cis-3) is discussed. Stereoselective effects on metastases of cis-3 and the previously reported trans-2 isomer were compared to conformationally mobile ICRF-159 [4,4''-(1-methyl-1,2-ethanediyl)bis(2,6-piperazinedione)] using a Syrian hamster lung adenocarcinoma (LG1002). Whereas ICRF-159 and cis-3 significantly inhibited lung metastases, the trans-2 isomer significantly increased the number of metastatic nodules in the lung. Antimetastatic activity can be separated from metastatic potentiating activity by controlling drug geometry.This publication has 2 references indexed in Scilit:
- Study of trans-cyclopropylbis(diketopiperazine) and chelating agents related to ICRF 159. Cytotoxicity, mutagenicity, and effects on scheduled and unscheduled DNA synthesisJournal of Medicinal Chemistry, 1977
- Three-membered Rings. The Preparation of Some 1,2-Cyclopropanedicarboxylic AcidsJournal of the American Chemical Society, 1958