102306-96-7Relevant academic research and scientific papers
NOVEL DERIVATIVE OF BETA-APOPICROPODOPHYLLIN AND METHOD OF PREPARING THEREOF
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Paragraph 0034-0036, (2021/11/13)
Provided are a novel derivative of β-apopicropodophyllin and a method of preparing the same, and more particularly, a compound represented by Formula 1 below, which is a novel derivative of β-apopicropodophyllin derived from podophyllotoxin, which is an anticancer agent, a method of preparing the same, and a composition for treating cancer, which includes the compound. In Formula 1, R is a C2 to C10 alkyl group, a C2 to C10 alkyl group containing an allyl- or alkyne, a —[CH2]n—C3 to C8 cycloalkyl group, a substituted or unsubstituted —[CH2]n-phenyl group, a substituted or unsubstituted —[CH2]n—C5 to C6 heteroaromatic group, a —C(═O)—C1 to C8 alkyl group, a substituted or unsubstituted —C(═O)—[CH2]n-phenyl group, or a substituted or unsubstituted —C(═O)—[CH2]n—C5 to C6 heteroaromatic group, wherein n is an integer of 0 to 6.
New compounds related to podophyllotoxin and congeners: synthesis, structure elucidation and biological testing.
Hansen,Jensen,Willumsen,Norskov-Lauritsen,Ebbesen,Nielsen,Buchardt
, p. 1190 - 1200 (2007/10/02)
4-Azido, 4-amino, 4-amido and 4-alkoxy compounds related to the lignans podophyllotoxin and 4'-demethylepipodophyllotoxin have been synthesized, and their structures elucidated. The Ritter reaction was shown to be useful in the preparation of the 4-amido compounds with the required stereochemistry. A preparative method for 4-chloro-4-deoxypicrophyllotoxin, for which all earlier synthetic attempts resulted in the two dehydrated compounds, alpha- and beta-apopicropodophyllotoxin, was developed. Supplementary preliminary studies of the biological activities of some of the compounds were performed. All compounds had pronounced inhibitory effect on the in vitro growth of human cervical cancer cells and TC-mouse cells with 4-amino-4-deoxypodophyllotoxin and 4-azido-4-deoxypodophyllotoxin showing the highest activity. Alkaline elution studies indicate that the toxicity of the 4'-demethoxy derivatives is due to protein-mediated DNA nicking. None of the compounds were found to have antiviral effect against herpes simplex type 2 (HSV-2), human immunodeficiency (HIV), and cytomegalovirus (CMV) in doses not toxic to the cells.
Antitumor Agents. 78. Inhibition of Human DNA Topoisomerase II by Podophyllotoxin and α-Peltatin Analogues
Thurston, Lee S.,Irie, Hiroshi,Tani, Shohei,Han, Fu-Sheng,Liu, Zong-Chao,et al.
, p. 1547 - 1550 (2007/10/02)
It has been reported that the action of etoposide (VP-16) (14) as an antitumor agent is mediated through its interaction with DNA topoisomerase II which results in DNA breakage inside the cell.In order to understand the mechanism of action as well as structure-activity relationships of 14, several novel, synthetic and some naturally occurring analogues related to podophyllotoxin were examined for inhibition of the DNA topoisomerase II activity.Compound 2 exhibited enhanced activity and compound 5 slightly diminished activity relative to 14.A 4β-substituted ether at the C ring and O-demethylation at the E ring appear to enhance activity.
