129392-85-4Relevant articles and documents
An efficient and practical method for the synthesis of mono-N-protected α,ω-diaminoalkanes
Lee, Jae Wook,Jun, Sung Im,Kim, Kimoon
, p. 2709 - 2711 (2001)
The large-scale synthesis of mono-N-protected (Cbz, Boc, Ts, and Ns) α,ω-diaminoalkanes (the number of carbon atoms=3, 4, 5 and 6) are accomplished in 81-94% yield by the protection of amine and subsequent reduction of an azido group from α,ω-azido alkyl amines. α,ω-Azido alkyl amines are prepared efficiently by the partial reduction of α,ω-diazidoalkanes which are obtained from the corresponding dibromoalkanes.
Comparative Studies of Three Pairs of α- And γ-Conjugated Folic Acid Derivatives Labeled with Fluorine-18
Boss, Silvan D.,Betzel, Thomas,Müller, Cristina,Fischer, Cindy R.,Haller, Stephanie,Reber, Josefine,Groehn, Viola,Schibli, Roger,Ametamey, Simon M.
, p. 74 - 86 (2016/02/05)
The folate receptor (FR) is upregulated in various epithelial cancer types (FR α-isoform), while healthy tissues show only restricted expression. FR-targeted imaging using folate radiopharmaceuticals is therefore a promising approach for the detection of FR-positive cancer tissue. Almost all folate-based radiopharmaceuticals have been prepared by conjugation at the γ-carboxylic functionality of the glutamate moiety of folic acid. In this work, three pairs of fluorinated α- and γ-conjugated folate derivatives were synthesized and their in vitro and in vivo properties compared. The syntheses of all six regioisomers were obtained in good chemical yields using a multistep synthetic approach including the highly selective Cu(I)-catalyzed 1,3-dipolar cycloaddition. The radiosyntheses of the α- and γ-conjugated 18F-labeled folate derivatives were accomplished in moderate to good radiochemical yields, high radiochemical purities (>95%), and specific activities ranging from 25 to 196 GBq/μmol. In vitro, all folate derivatives showed high binding affinity to the FR-α (IC50 = 1.4-2.2 nM). In vivo PET imaging and biodistribution studies in FR-positive KB tumor-bearing mice demonstrated similar FR-specific tumor uptake for both regioisomers of each pair of compounds. However, FR-unspecific liver uptake was significantly lower for the α-regioisomers compared to the corresponding γ-regioisomers. In contrast, kidney uptake was up to 50% lower for the γ-regioisomers than for the α-regioisomers. These results show that the site of conjugation in the glutamyl moiety of folic acid has a significant impact on the in vivo behavior of 18F-based radiofolates, but not on their in vitro FR-binding affinity. These findings may potentially stimulate new directions for the design of novel 18F-labeled folate-based radiotracers.
Synthesis, biological activity and structural study of new benzotriazole-based protein kinase CK2 inhibitors
Swider,Maslyk,Zapico,Coderch,Panchuk,Skorokhyd,Schnitzler,Niefind,De Pascual-Teresa,Ramos
, p. 72482 - 72494 (2015/09/15)
A new series of 4,5,6,7-tetrabromobenzotriazole (TBB) derivatives was synthesized and characterized as CK2 inhibitors. They were readily synthesized using a click chemistry approach based on a Cu(i)-catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC). Some of the synthesized compounds present interesting inhibitory activities using an in vitro assay, with Ki values in the low micro molar range and a high degree of selectivity against a panel of 24 kinases. Selected compounds were tested for their antiproliferative effect on several cancer cell lines, and for their proapoptotic activity towards human Jurkat T-leukemia and MCF-7 breast adenocarcinoma cells, showing that they can be proposed as promising anticancer agents. Docking studies as well as crystallographic analysis allowed us to identify ligand-CK2 interactions that account for the molecular recognition process, and can help to further optimize this family of compounds as CK2 inhibitors.
