1256-91-3Relevant academic research and scientific papers
Synthesis and biological evaluation of podophyllotoxin congeners as tubulin polymerization inhibitors
Kamal, Ahmed,Srinivasa Reddy,Polepalli, Sowjanya,Shalini, Nekkanti,Reddy, V. Ganga,Subba Rao,Jain, Nishant,Shankaraiah, Nagula
, p. 5466 - 5475 (2015/02/02)
A series of new podophyllotoxin derivatives containing structural modifications at C-7, C-8, and C-9 were synthesized and evaluated for their cytotoxic activity against three human cancer cell lines. All the synthesized compounds showed significant growth inhibition with GI50values in micromolar levels while some of the compounds were several times more potent against MCF-7 and HeLa cell lines than MIAPACA cell line. Three compounds (12a, 12d and 12e) emerged as potent compounds with broad spectrum of cytotoxic activity against all the tested cell lines with GI50values in the range of 0.01-2.1 μM. These compounds induce microtubule depolymerization and arrests cells at the G2/M phase of the cell cycle. Moreover, compounds 12d and 12e disrupted microtubule network and accumulated tubulin in the soluble fraction in a similar manner to their parent podophyllotoxin scaffold. In addition, structure activity relationship studies within the series were also discussed. Molecular docking studies of these compounds into the colchicine-binding site of tubulin, revealed possible mode of inhibition by these compounds.
Novel D-ring analogues of podophyllotoxin as potent anti-cancer agents
Subrahmanyam, Duvvuri,Renuka,Rao, C.V. Laxmana,Sagar, P. Sangeeta,Deevi, Dhanvanthri S.,Babu, J. Moses,Vyas
, p. 1391 - 1396 (2007/10/03)
Several D-ring modified analogues of podophyllotoxin were prepared viz semi-synthesis starting from naturally occuring podophyllotoxin and determined their in vitro anti-cancer activity. Most of the analogues have shown good activity towards human cancer cell lines.
Asymmetric total synthesis of (-)-podophyllotoxin
Bush, Edward J.,Jones, David W.
, p. 151 - 155 (2007/10/03)
(-)-Podophyllotoxin of 98% optical purity has been synthesized in eight steps and in 15% overall yield. The key step, Diels-Alder addition of the o-quinonoid pyrone 2 [6,7-methylenedioxy-1-(3,4,5-trimethoxyphenyl)-2-benzopyran-3-one] to the chiral dienophile 5 [5-(-)-menthyloxyfuran-2(5H)-one], proceeds with very high regio-, endo- and facial selectivity.
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
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
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
Synthesis of Podophyllum Lignans via an Isolable o-Quinonoid Pyrone
Jones, David W.,Thompson, Adrian M.
, p. 1797 - 1798 (2007/10/02)
The 2-benzopyran-3-one (7) is a stable, isolable, and useful Diels-Alder diene; its adduct (10) formed with dimethyl fumarate is transformed in three steps into methyl epipodophyllate (14) which gives epipodophyllotoxin (2) (81percent) by direct lactonisation (ZnCl2-tetrahydrofuran-4 Angstroem molecular sieves).
