501447-34-3Relevant academic research and scientific papers
Synthesis of novel pyrido [3′,2′:5,6]thiopyrano[3,2-b]indol-5(6H)-ones and 6H-pyrido[3′,2′:5,6]thiopyrano[4,3-b]quinolines, two new heterocyclic ring systems
Da Settimo, Antonio,Marini, Anna Maria,Primofiore, Giampaolo,Da Settimo, Federico,Salerno, Silvia,Simorini, Francesca,Pardi, Gianluca,La Motta, Concettina,Bertini, Daniele
, p. 1001 - 1006 (2002)
The synthesis of new pyrido [3′,2′: 5,6]thiopyrano [3,2-b]indol-5 (6H)-ones was accomplished by the Fischer-indole cyclization of some 2,3-dihydro-3-phenylhydrazonothiopyrano[2,3-b]pyridin-4(4H)-ones, obtained from the 2,3-dihydro-3-hydroxymethylenethiopy
Benzothiopyranoindole- and pyridothiopyranoindole-based antiproliferative agents targeting topoisomerases
Salerno, Silvia,La Pietra, Valeria,Hyeraci, Mariafrancesca,Taliani, Sabrina,Robello, Marco,Barresi, Elisabetta,Milite, Ciro,Simorini, Francesca,García-Argáez, Aída Nelly,Marinelli, Luciana,Novellino, Ettore,Da Settimo, Federico,Marini, Anna Maria,Dalla Via, Lisa
, p. 46 - 58 (2019/01/21)
New benzothiopyranoindoles (5a-l) and pyridothiopyranoindoles (5m-t), featuring different combinations of substituents (H, Cl, OCH3) at R2-R4 positions and protonatable R1-dialkylaminoalkyl chains, were synthesized and biologically assayed on three human tumor cell lines, showing significant antiproliferative activity (GI50 values spanning from 0.31 to 6.93 μM) and pro-apoptotic effect. Linear flow dichroism experiments indicate the ability of both chromophores to form a molecular complex with DNA, following an intercalative mode of binding. All compounds displayed a moderate ability to inhibit the relaxation activity of both topoisomerases I and II, reasonably correlated to their intercalative capacities. Cleavable assay performed with topoisomerase I revealed a significant poisoning effect for compounds 5g, 5h, 5s, and 5t. A theoretical model provided by hydrated docking calculations clarified the role of the R1-R4 substituents on the topoisomerase I poison activity, revealing a crucial role of the R2-OCH3 group.
