The tert-butyl dimethyl silyl group as an enhancer of drug cytotoxicity against human tumor cells

Tuning the cytotoxicity of ruthenium(ii) para-cymene complexes by mono-substitution at a triphenylphosphine/phenoxydiphenylphosphine ligand

“…As a matter of fact, tert-butyl dimethyl silyl, tethered to tetrahydropyran rings, was previously indicated as an enhancer of cytotoxicity against HL60 human leukemia cells and MCF7 breast cancer cells in vitro, due to its lipophilicity favouring the cellular uptake of the drug. 31 It is possible that the drop of activity observed on moving from 1-2 to 3 is related to some unexpected effect associated with dichloroacetic acid, 19 which may be released from 3 inside the cells by means of intracellular esterases. 32 Compounds homologous to 3, [RuCl 2 (η 6 -p-cymene)(κP-Ph 2 PAr BIO )], derivatized with bioactive carboxylic acids different from CHCl 2 CO 2 H, displayed variable cytotoxic activity towards A2780 and A2780cisR cancer cell lines (see Introduction) and, in one case (derivatization with Indomethacin), not appreciable activity.…”

“…Cl NMR (acq. time 10 min): no signal.DMSO 6H), 9H), 5.27 (d, J = 5.9 Hz, 2H), 5.21 (d, J = 5.6 Hz, 2H), 1.74 (s, 3H), 0.93 (d, J = 6.8 Hz, 6H) 31. P{ 1 H} NMR: δ/ppm = 24.2.…”

Silyl modification of biologically active compounds. 13. Synthesis, cytotoxicity and antibacterial action of N‐methyl‐N‐(2‐triorganylsiloxyethyl)‐1,2,3,4‐tetrahydro(iso)quinolinium iodides

“…A comparison of 8, 12a-i and 13 with 3 and 4 provided evidence that the latter compounds R 1 R 2 R 3 : Et 2 Me (9a, 12a); Et 3 (9b, 12b); EtBu 2 (9c, 12c); MeHp 2 (9d, 12d); Me 2 Oct (9e, 12e); Me 2 Dc (9f, 10, 11, 12f, 13, 14); Me 2 (C 11 H 23 ) (9g, 12g); Me 2 (C 16 possessed lower biological activity, practically did not reveal cytotoxic properties and in general were less active concerning the microbial strains examined. A comparison of 8, 12a-i and 13 with 3 and 4 provided evidence that the latter compounds R 1 R 2 R 3 : Et 2 Me (9a, 12a); Et 3 (9b, 12b); EtBu 2 (9c, 12c); MeHp 2 (9d, 12d); Me 2 Oct (9e, 12e); Me 2 Dc (9f, 10, 11, 12f, 13, 14); Me 2 (C 11 H 23 ) (9g, 12g); Me 2 (C 16 possessed lower biological activity, practically did not reveal cytotoxic properties and in general were less active concerning the microbial strains examined.…”

“…[14] Its 2 0 ,3 0 -bis-O-tert-butyldimethylsilyl derivative exhibited broad-spectrum antiproliferative activity and was accepted as a new member of the N 6 ,5 0 -bis-ureidoadenosine class of anticancer nucleosides. [16] 5 0 -Triphenylsilyl modification of deoxyuridine acyclic analogues resulted in obtaining more potent inhibitors of Plasmodium falciparum deoxyuridine 5 0 -triphosphate nucleotidohydrolase, a target for the development of antimalarial drugs, in comparison with their 5 0 -trityloxy derivatives. [16] 5 0 -Triphenylsilyl modification of deoxyuridine acyclic analogues resulted in obtaining more potent inhibitors of Plasmodium falciparum deoxyuridine 5 0 -triphosphate nucleotidohydrolase, a target for the development of antimalarial drugs, in comparison with their 5 0 -trityloxy derivatives.…”

A Short and Efficient Enantiomeric Synthesis of Antitumor Fused Tetrahydrofurans

“…Within our program directed at the asymmetric total synthesis of novel antitumor compounds [5] and bioactive sub- [ stances of marine origin, [6] these synthetically challenging ring systems have attracted our interest and we have sought to develop new methodologies for their enantiomerically pure synthesis. In this study, a series of stereoisomeric derivatives of fTHFs substituted with diverse protecting groups either at the primary or secondary hydroxy groups were synthesized by means of a short and highly efficient synthetic methodology.…”