71645-10-8

Upstream product

• 71645-07-3 N-(4-oxyl-2,2,6,6-tetramethylpiperidinyloxycarbonyl)-imidazole 
• 63-91-2 L-phenylalanine 
• 71645-06-2 N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyloxycarbonyl)-imidazolium tosylate 
• 71645-05-1 N-(1-ylooxy-2,2,6,6-tetramethylpiperidinyloxycarbonyl)-imidazole 
• 2403-88-5 4-hydroxy-2,2,6,6-tetramethylpiperidine 
• 45985-24-8 TEMPOL 

Downstream Products

• 1216943-84-8 C₄₀H₄₆N₃O₁₁ 
• 1357089-92-9 C₄₂H₄₉N₂O₁₀ 
• 1350766-46-9 3'-N-[N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinylcarbonyl)-L-phenylalaninyl]-amido-AVE8063 
• 872579-13-0 C₄₁H₄₇N₂O₁₂ 

Relevant academic research and scientific papers

Synthesis of novel spin-labeled derivatives of 5-FU as potential antineoplastic agents

Chemotherapy is a general treatment option for various cancers, including lung cancer. In order to find compounds with superior bioactivity and less toxicity against lung cancer, novel spin-labeled 5-fluorouracil (5-FU) derivatives (3a-f) were synthesized and evaluated against four human tumor cell lines (A-549, DU-145, KB, and KBvin). Two promising compounds 3d and 3f exhibited IC50 values of 2.76 and 2.38 μM, respectively, against non-small cell lung carcinoma cell line A-549. These compounds were twofold more cytotoxic than 5-FU and less toxic against other tested cell lines. Compound 3f exhibited seven times more selective cytotoxicity against A-549 than 5-FU. Our results suggest that compounds 3d and 3f merit further investigation for development into clinical trial candidates for non-small cell lung cancer.

Synthesis and mechanistic studies of novel spin-labeled combretastatin derivatives as potential antineoplastic agents

Two series (14a-d and 21a-h) of novel spin-labeled combretastatin derivatives were synthesized and evaluated for cytotoxicity against four tumor cell lines (K562, SGC-7901, Hela and HepG-2). Simultaneously, a representative compound 21a was selected to investigate the antitumor mechanisms of these synthetic compounds. The results indicated that some of the compounds showed significant cytotoxicity against four tumor cell lines in vitro and were more active than etoposide, a clinically available anticancer drug. Among the newly synthesized compounds, 21a, 21b and 21c displayed the greatest cytotoxicity against three tested tumor cell lines (HEPG-2, BGC-832 and Hela), with IC 50 values ranging from 0.15 to 1.05 μM, compared with values of 0.014-0.403 μM for 3-amino-deoxycombretastatin A-4 (3). In addition, the mechanistic analysis revealed that compound 21a effectively interfered with tubulin dynamics to prevent mitosis in cancer cells, leading to cell cycle arrest and, eventually, dose dependent apoptosis.

Design, synthesis and cytotoxic activity of novel spin-labeled rotenone derivatives

Three series of novel spin-labeled rotenone derivatives were synthesized and evaluated for cytotoxicity against four tumor cell lines, A-549, DU-145, KB and KBvin. All of the derivatives showed promising in vitro cytotoxic activity against the tumor cell lines tested, with IC50 values ranging from 0.075 to 0.738 μg/mL. Remarkably, all of the compounds were more potent than paclitaxel against KBvin in vitro, and compounds 3a and 3d displayed the highest cytotoxicity against this cell line (IC50 0.075 and 0.092 μg/mL, respectively). Based on the observed cytotoxicity, structure-activity relationships have been described.

First synthesis and biological evaluation of novel spin-labeled derivatives of deoxypodophyllotoxin

Deoxypodophyllotoxin inhibits tubulin polymerization and induces cell cycle arrest at G2/M, followed by apoptosis. In order to find compounds with superior bioactivity and less toxicity, a series of spin-labeled derivatives of deoxypodophyllotoxin were synthesized by reacting 4′-demethyl-4-deoxypodophyllotoxin (DPPT) with N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyloxycarbonyl) amino acids. The cytotoxic activities against three tumor cell lines (HL-60, RPMI-8226, A-549) in vitro and the antioxidative activities in tissues of Sprague Dawley (SD) rats of target compounds were evaluated, and the results indicated that compounds 11a-h were more potent in terms of cytotoxicities and antioxidative activities than either parent compound DPPT or anticancer drug VP-16.

Novel semisynthetic spin-labeled derivatives of podophyllotoxin with cytotoxic and antioxidative activity

A series of novel spin-labeled podophyllotoxin derivatives were synthesized by reacting the corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4-piperidinyloxy carbonyl)-amino acids with 4β-amino-4′-demethylepipodophyllotoxin. The synthesized derivatives 12a-g were evaluated for the partition coefficients, cytotoxicities in vitro against three tumor cell lines (A-549, HL-60, and RPMI-8226) and antioxidative activities in tissues of SD rats by the TBA method. The vast majority of target compounds have shown superior or comparable activities against A-549, HL-60, and RPMI-8226 compared to VP-16, and they have shown more significant antioxidative activities and superior water solubility than VP-16.

Synthesis of novel spin-labeled derivatives of podophyllotoxin as potential antineoplastic agents

Five novel nitroxyl spin-labeled ester derivatives of podophyllotoxin have been prepared by reacting the corresponding N-(1-oxyl-2,2,6,6-tetramethyl-4- piperidinyloxy-carbonyl) amino acids with the hydroxy group of podophyllotoxin in the presence of dimethylaminopyridine and N,N-dicyclohexylcarbodiimide and evaluated as potential antitumor agents. All of the target compounds showed more significant cytotoxicity against P-388 murine leukemia and A-549 human lung carcinoma in vitro than etoposide. Copyright Taylor & Francis, Inc.