69914-72-3Relevant academic research and scientific papers
Sn(II)-Mediated facile approach for the synthesis of 2-aryl-2: H -indazole-3-phosphonates and their anticancer activities
Sudhapriya,Balachandran,Awale,Perumal
, p. 5582 - 5594 (2017/07/10)
A convenient three-component method was developed for the synthesis of various 2-aryl-2H-indazole-3-phosphonates using SnCl2·2H2O under conventional heating techniques. The transition metal free reaction, mild reaction conditions, one-pot operation, open flask conditions, wide substrate scope and good yields are a few important features of this methodology. This protocol proceeds with high atom economy via the formation of α-aminophosphonates followed by the generation of an indazole ring through N-N bond formation, eliminating water as a by-product. The cytotoxic properties of the 2-aryl-2H-indazole-3-phosphonate derivatives were investigated against A549 and HepG-2 cells. Interestingly, compounds 4d and 4g showed potent cytotoxic properties against HepG-2 cells and compound 4p showed significant cytotoxic properties against A549 cells. Intracellular visualization was done using a laser scanning confocal microscope. DNA fragmentation, colony formation, and apoptosis studies, flow cytometry and western blot analysis for 4p against A549 cells have also been reported.
Synthesis, X-ray crystal structure, DNA/protein binding and cytotoxicity studies of five α-aminophosphonate N-derivatives
Wang, Qingming,Yang, Lei,Ding, Hui,Chen, Xuanrong,Wang, Hua,Tang, Xinhui
, p. 132 - 139 (2016/11/11)
Five new α-aminophosphonates are synthesized and characterized by EA, FT-IR, 1H NMR, 13C NMR, 31P NMR, ESI-MS and X-ray crystallography. The X-ray analyses reveal that the crystal structures of 1–5 are monoclinic or triclinic system with the space group P 21/c, P ? 1, P ? 1, P2(1)/c and P ? 1, respectively. All P atoms of 1–5 have tetrahedral geometries involving two O-ethyl groups, one Cα atom, and a double bond O atom. The binding interaction of five new α-aminophosphonate N-derivatives (1–5) with calf thymus(CT)-DNA have been investigated by UV–visible and fluorescence emission spectrometry. The apparent binding constant (Kapp) values follows the order: 1 (3.38 × 105 M?1) > 2 (3.04 × 105 M?1) > 4 (2.52 × 105 M?1) > 5 (2.32 × 105 M?1) > 3 (2.10 × 105 M?1), suggesting moderate intercalative binding mode between the compounds and DNA. In addition, fluorescence spectrometry of bovine serum albumin (BSA) with the compounds 1–5 showed that the quenching mechanism might be a static quenching procedure. For the compounds 1–5, the number of binding sites were about one for BSA and the binding constants follow the order: 1 (2.72 × 104 M?1) > 2 (2.27 × 104 M?1) > 4 (2.08 × 104 M?1) > 5 (1.79 × 104 M?1) > 3 (1.17 × 104 M?1). Moreover, the DNA cleavage abilities of 1 exhibit remarkable changes and the in vitro cytotoxicity of 1 on tumor cells lines (MCF-7, HepG2 and HT29) have been examined by MTT and shown antitumor effect on the tested cells.
An efficient and convenient procedure for the one-pot synthesis of α-aminophosphonates from aryl azides under solvent-free conditions
Yu, Ya-Qin
, p. 2545 - 2550 (2013/09/24)
A novel and simple approach to the multicomponent one-pot reaction of aldehydes, diethyl phosphite, and azides to form α-aminophosphonates under solvent-free conditions at room temperature has been developed. In the presence of iodine and iron, aryl azides were, for the first time, used as substrates for the synthesis of α-aminophosphonates. The reactions were completed within 5 minutes to 12 hours and afforded the corresponding products in good yields.
