78216-03-2Relevant academic research and scientific papers
Synthesis and biological evaluation of new podophyllic aldehyde derivatives with cytotoxic and apoptosis-inducing activities
Castro, Ma. ángeles,Miguel Del Corral, José Ma.,García, Pablo A.,Rojo, Ma. Victoria,De La Iglesia-Vicente, Janis,Mollinedo, Faustino,Cuevas, Carmen,San Feliciano, Arturo
scheme or table, p. 983 - 993 (2010/07/16)
Several series of nonlactonic podophyllic aldehyde analogues were prepared and evaluated against several human tumor cell lines. They had different combinations of aldehyde, imine, amine, ester, and amide functions at C-9 and C-9′ of the cyclolignan skeleton. All the compounds synthesized showed cytotoxicity levels in the μM range and below. Within the new series tested, compounds having an aldehyde or imine at C-9 and an ester at C-9′ were the most potent, with GI50 values in the nM range, some of them being several times more potent against HT-29 and A-549 carcinoma than against MB-231 melanoma cells. Cell cycle studies and analysis of the microtubule-disrupting capacity have demonstrated the existence of two different mechanisms of cell death induction for compounds with closely related structures.
Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring
Gordaliza, Marina,Castro, M. Angeles,Miguel del Corral, Jose M.,Lopez-Vazquez, M. Luisa,Garcia, Pablo A.,Feliciano, Arturo San,Garcia-Gravalos, M. Dolores,Broughton, Howard
, p. 15743 - 15760 (2007/10/03)
Several cyclolignans lacking of the Iactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the 3 aldehyde 9 (methyl 9-deoxy-9-oxo-α-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the correspnding saturated aldehyde 13 in comparison with podophyllotoxin.
Immunosuppressive cyclolignans
Gordaliza, Marina,Faircloth, Glynn T.,Castro, Ma. Angeles,Miguel Del Corral, José M.,López-Vázquez, Ma. Luisa,San Feliciano, Arturo
, p. 2865 - 2868 (2007/10/03)
The immunosuppressive activity of several lactonic, nonlactonic, and heterocycle-fused cyclolignans has been demonstrated for the first time by use of a T-cell-mediated immune response. Of the compounds tested, 4'- demethyldeoxypodophyllotoxin (8), β-apopicropodophyllin (6), and the isoxazoline-fused cyclolignan 15 are the most potent with respect to their suppression of activated splenocytes.
Synthesis of (+/-)-4-Deoxypodophyllotoxin, (+/-)-Podophyllotoxin and (+/-)-Epipodophyllotoxin
Jones David W.,Thompson, Adrian M.
, p. 2541 - 2548 (2007/10/02)
6,7-Methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 1 and dimethyl fumarate in acetonitrile give mostly the C-2 exo-CO2Me adduct 4 which is transformed in four steps into epipodophyllotoxin 10a.Attempted addition of dimethyl maleate to 1 p
Synthesis of Podophyllum Lignans via an Isolable o-Quinonoid Pyrone
Jones, David W.,Thompson, Adrian M.
, p. 2533 - 2540 (2007/10/02)
The 2-benzopyran-3-one 10 is a stable, isolable and useful Diels-Alder diene; its methyl 4-benzoyloxycrotonate adduct 23 formed regioselectively and stereoselectively in acetonitrile is reduced with H2/Pd to give 31 with inversion of C-1 stereochemistry.T
Comprehensive Synthetic Route to Eight Diastereomeric Podophyllum Lignans
Forsey, Steven P.,Rajapaksa, Dayananda,Taylor, Nicholas J.,Rodrigo, Russell
, p. 4280 - 4290 (2007/10/02)
An oxabicyclo compound, 9, prepared in 47percent yield through an isobenzofuran intermediate was converted with excellent regio- and stereocontrol to eight (+/-)-lignan lactones of the podophyllotoxin series.One of the eight, epiisopicropodophyllin, 36, t
A Stereo- and Regiocontrolled Synthesis of Podophyllum Lignans
Rodrigo, Russell
, p. 4538 - 4540 (2007/10/02)
A Diels-Alder adduct of an isobenzofuran (generated in situ) and dimethyl acetylenedicarboxylate is converted by a series of controlled reductions and isomerizations to the lignans deoxy- and isodeoxypodophyllotoxin in seven stages.
