6559-91-7Relevant articles and documents
Synthesis and Biological Activity of Ferrocenyl and Ruthenocenyl Analogues of Etoposide: Discovery of a Novel Dual Inhibitor of Topoisomerase II Activity and Tubulin Polymerization
Chrab?szcz, Karolina,B?au?, Andrzej,Grucha?a, Martyna,Wachulec, Marcin,Rychlik, B?a?ej,Pla?uk, Damian
, p. 6254 - 6262 (2021/03/09)
Two series of the ferrocenyl and ruthenocenyl analogues of etoposide bearing 1,2,3-triazolyl or aminoalkyl linker were synthesized and evaluated for their cytotoxic properties, influence on the cell cycle, ability to induce tubulin polymerization, and inhibition of topoisomerase II activity. We found that the replacement of the etoposide carbohydrate moiety with a metallocenyl group led to organometallic conjugates exhibiting differentiated antiproliferative activity. Biological studies demonstrated that two ferrocenylalkylamino conjugates were notably more active than etoposide, with submicromolar or low-micromolar IC50 values towards SW620, etoposide-resistant SW620E, and methotrexate-resistant SW620M cancer cell lines. Moreover, the simplest ferrocenylmethylamino conjugate exerted dual inhibitory action against tubulin polymerization and topoisomerase II activity while other studied compounds affected only topoisomerase II activity.
Preparation method for total synthesis of 4'-demethylepipodophyllotoxin
-
Paragraph 0023; 0041; 0055; 0056, (2020/06/02)
The invention discloses a preparation method for total synthesis of 4'-demethylepipodophyllotoxin (also named as epipodophyllotoxin). The preparation method comprises the following steps: (1) syringaldehyde (compound 1) used as an initial material and benzyl methoxyacyl used as a protective group are in favor of a chemical reaction of finally removing the protective group to obtain a target compound; (2) a chiral target object is produced by adopting an asymmetric hydrogenation reduction reaction in which a chiral ligand (s-BINAN Ru (II)) participates; and (3) a reaction of hydrogenating and deprotecting groups is also carried out in parallel while chiral catalytic hydrogenation is carried out. The reaction steps and treatment are saved, the route selection is targeted to the target compound, the production cost is low, and the environment is friendly.
Synthesis and Biological evaluation of novel 4β-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxins as anticancer compounds
Hyder, Irfan,Yedlapudi, Deepthi,Kalivendi, Shasi V.,Khazir, Jabeena,Ismail, Tabasum,Nalla, Naresh,Miryala, Sreekanth,Sampath Kumar, Halmuthur M.
supporting information, p. 2860 - 2863 (2015/06/08)
A series of novel 4β-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxin derivatives were synthesized by employing azide-nitrile click chemistry approach. All the derivatives were evaluated for their cytotoxicity against a panel of four human cancer cell lines and their IC50 values were found to be in the range of 2.4-29.06 μM. The cytotoxicity exhibited by the majority of test compounds were found to comparable and often more effective than doxorubicin and all compounds exhibited higher cytotoxicity on A-549 cell lines. Cell cycle analysis showed that the novel 4β-[(5-substituted)-1,2,3,4-tetrazolyl] podophyllotoxins resulted in cell cycle arrest at G2/M phase and were also found to be the potent inhibitors of tubulin polymerization in vitro.