62287-47-2Relevant academic research and scientific papers
Synthesis of podophyllotoxin analogues: δ-lactone-containing picropodophyllin, podophyllotoxin and 4′-demethyl-epipodophyllotoxin derivatives
Meresse, Philippe,Monneret, Claude,Bertounesque, Emmanuel
, p. 2657 - 2671 (2007/10/03)
Non-epimerizable cis and trans δ-lactone analogues of podophyllotoxin have been prepared. Thus the synthesis of the cis isomer 4 has been achieved in 8 steps and 4% overall yield from podophyllotoxin 1 via the reduction of the γ lactone ring into the tran
Modes of methyleneoxy bridging and their effect on tetrahydronaphthalene lignan cytotoxicity
LaLonde, Robert T.,Ramdayal, Frank,Sarko, Anatole,Yanai, Koichi,Zhang, Mianji
, p. 1180 - 1190 (2007/10/03)
Dioxatricyclodecane, oxabicyclooctane, and benzodihydropyran derivatives of α-conidendrin (ACON), podophyllotoxin (PT), and sikkimotoxin (SK) were prepared to learn which methyleneoxy bridging modes and arene and aryl substituents coincided with high cytotoxicity. PT-derived dioxatricyclodecane 14 showed in vitro activity at 10-8 M. SK analogue 12 was less active, and ACON analogue 11 was inactive at 10-4 M. In vivo intraperitoneal and subcutaneous activities of 14 were observed. In vitro cytotoxicities were higher for oxabicyclooctanes when hydroxymethyl group and methyleneoxy bridge were cis, as in deoxypicropodophyllin analog 20, rather than trans, as in PT analogue 5. Acetylation of the hydroxymethyl group of 20 lowered activities, whereas acetylation of 5 increased or lowered activities. Reduction of the hydroxymethyl group of 5 to a methyl group increased cytotoxicities. Molecular dynamics indicated the THN scaffold of benzodihydropyrans was conformationally mobile, but scaffolds of oxabicyclooctanes and dioxatricyclodecanes were immobile. Each of three PT-benzodihydropyrans was less active than its oxabicyclooctane counterpart.
Cytotoxic cyclolignans related to podophyllotoxin
Gordaliza, Marina,Miguel Del Corral, Jose M.,Angeles Castro,Garcia-Garcia, Pablo A.,San Feliciano, Arturo
, p. 297 - 304 (2007/10/03)
The cyclolignan family of natural products includes compounds with important antineoplastic and antiviral properties such as podophyllotoxin and two of their semisynthetic derivatives, etoposide and teniposide. The latter are included in a wide variety of
