141473-49-6Relevant articles and documents
Preparation of octaethyl-3-amino-pentane-1,1,5,5-tetrakisphosphonate by catalytic hydrogenation of the corresponding 3-nitro-compound
Winckler,Pieper,Keppler
, p. 137 - 141 (1996)
The aim of this investigation was to find a convenient synthetical access to tetraethyl-3-amino-1,1-bisphosphonates, a class of chemical compounds which are useful agents in the concept of osteotic vectorisation of antitumor and antiinflammatory drugs. Base-catalyzed addition of nitroalkanes to tetraethylethenylidenebisphosphonate 1 affords the tetraethyl-3-nitro-alkane-1,1-bisphosphonates 3 and 4 and octaethyl-3-nitro-pentane-1,1,5,5-tetrakisphospnonate 2, which can be hydrogenated to the corresponding 3-amino-alkane-1,1-bisphosphonates 6 and 7 and the title compound octaethyl-3-amino-pentane-1,1,5,5-tetrakisphosphonate 5.
Novel ferrocenylbisphosphonate hybrid compounds: Synthesis, characterization and potent activity against cancer cell lines
Aderibigbe, Blessing A.,Adeyemi, Samson A.,Anusionwu, Chioma G.,Choonara, Yahya E.,Oselusi, Samson O.,Ubanako, Philemon,Yangkou Mbianda, Xavier
, (2022/02/17)
The toxicity of existing anticancer agents on healthy cells and the emergence of multidrug-resistance cancer cells have led to the search for less toxic anticancer agents with different mechanisms of action. In this study, a novel class of ferrocenylbisphosphonate hybrid compounds (H1-H8) were designed and characterized using NMR, IR and HRMS. The in vitro anticancer activity of the hybrid compounds on HeLa (cervix adenocarcinoma) and A549 (non-small cell lung cancer cell lines) was evaluated. The structure–activity relationship of the hybrid molecules was also studied. The lead compound, tetraethyl (3-(4-oxo-4-ferrocenylbutanamido) propane-1-1-diylbis(phosphonate) (H6) exhibited higher cytotoxicity on A549 (IC50 = 28.15 μM) than cisplatin (IC50 = 58.28 μM), while its activity on HeLa cells (IC50 = 14.69 μM) was equivalent to that of cisplatin 15.10 μM (HeLa cells). H6 (IC50 = 95.58 μM) was also five times less toxic than cisplatin (IC50 = 20.86 μM) on fibroblast NIH3T3 suggesting that H6 can be a future replacement for cisplatin due to its non-toxicity to healthy cells. Interestingly, some ferrocene and bisphosphonate parent compounds exhibited promising anticancer activity with 4-ferrocenyl-4-oxobutanoic acid (FI) exhibiting higher cytotoxic activity (IC50 = 1.73 μM) than paclitaxel (IC50 = 3.5 μM) on A549 cell lines. F1 also exhibited lower cytotoxicity than paclitaxel and cisplatin on the normal murine fibroblast cell line (NIH3T3). The molecular docking studies showed H6 strong binding affinity for the STAT3 signaling pathway in A549 cell line, and the MAdCAM-1 and cellular tumor antigen p53 proteins in HeLa cell lines.
Design of a radiopharmaceutical for the palliation of painful bone metastases: Rhenium-186-labeled bisphosphonate derivative
Ogawa, Kazuma,Mukai, Takahiro,Arano, Yasushi,Hanaoka, Hirofumi,Hashimoto, Kazuyuki,Nishimura, Hiroshi,Saji, Hideo
, p. 753 - 761 (2007/10/03)
To develop a radiopharmaceutical for the palliation of painful bone metastases based on the concept of bifunctional radiopharmaceuticals, we designed a bisphosphonate derivative attached to a stable 186Re- monoaminemonoamidedithiol (MAMA) chela
