1038997-68-0Relevant academic research and scientific papers
Synthesis and cytotoxicity of O,O′-dialkyl {[2-(substituted phenoxy)acetamido](substituted phenyl)methyl}phosphonates
Ning, Lihong,Wang, Wei,Liang, Yongju,Peng, Hao,Fu, Liwu,He, Hongwu
experimental part, p. 379 - 384 (2012/03/13)
A series of O,O′-dialkyl {[2-(substituted phenoxy)acetamido] (substituted phenyl)methyl}phosphonates was synthesized and their cytotoxic activities were tested against various human tumor cell lines. Some compounds (5q, 5r, 5s, 5w, 5x and 5y) showed relatively high cytotoxicity. Especially, compounds 5x and 5q exhibited the best cytotoxicity against KB and CNE2 cells with IC50 7.1 and 11.4 μM, respectively. Their inhibitory activities against KB and CNE2 cells were even higher than that of fluorouracil.
Synthesis and antiviral activity of novel pyrazole amides containing α-aminophosphonate moiety
Wu, Lintao,Song, Baoan,Bhadury, Pinaki S.,Yang, Song,Hu, Deyu,Jin, Linhong
scheme or table, p. 389 - 396 (2011/06/20)
A series of novel pyrazole amides J1-J15 containing an α-aminophosphonate moiety were synthesized and subsequently characterized by spectral (IR, 1H-, 13C-, 31P-, and 19F-NMR) data and elemental analysis. The racemic sample of J1 was further separated into its enantiomers under normal-phase condition on two immobilized polysaccharide-based chiral stationary phases (Chiralpak IA and Chiralpak IC). The synthesized compounds revealed certain degree of antiviral activity in the bioassay. The title compounds (J 3, J10, and J12) showed some curative activities (39.9%, 41.8%, 50.1%, respectively) against tobacco mosaic virus at 0.5 mg/mL.
Synthesis and antiviral bioactivities of novel chiral bis-thiourea-type derivatives containing α-aminophosphonate moiety
Yang, Xuan,Song, Baoan,Jin, Linhong,Wei, Xue,Bhadury, S. Pinaki,Li, Xiangyang,Yang, Song,Hu, Deyu
scheme or table, p. 103 - 109 (2011/12/21)
Starting from 1-((1R,2R)-2-aminocyclohexyl)-3-substituted thioureas (3a-c) and substituted isothiocyanates (9a-d), chiral bis-thiourea derivatives containing α-aminophosphonate moiety 10a-l were prepared and completely characterized by elemental analysis, physical and spectral (IR, 1H NMR, 13C NMR, 31P NMR) data. The results of bioassay revealed that compounds 10a and 10e possessed appreciable curative bioactivities on cucumber mosaic virus (CMV) at 0.5 mg/mL in vivo (inhibitory rate = 60.3%, 64.8% respectively) and tobacco mosaic virus (TMV) at 0.5 mg/mL in vivo (inhibitory rate = 50.3%, 50.8% respectively), which were comparable to the values shown by standard reference (58.7%) and commercial product Ningnanmycin (56.3%), respectively. Chiral compound 10e displayed more potent antiviral activity (EC50 = 0.149 mg/mL) than Ningnanmycin (EC50 = 0.201mg/mL) against CMV.
Synthesis and antiviral activities of amide derivatives containing the &α-aminophosphonate moiety
Hu, De-Yu,Wan, Qiong-Qiong,Yang, Song,Song, Bao-An,Bhadury, Pinaki S.,Jin, Lin-Hong,Yan, Kai,Liu, Fang,Chen, Zhuo,Xue, Wei
supporting information; experimental part, p. 998 - 1001 (2009/05/07)
Starting from (substituted-)benzaldehydes, the title compounds 6 were synthesized through five step reactions. Benzaldehydes were treated with ammonium hydroxide, followed by dialkyl phosphite, to give dialkyl N-(arylmethylene)-1-amino-1-aryl methylphosphonates (3). Phosphonates 3 were then easily hydrolyzed to give dialkyl 1-amino-1-aryl-methylphosphonates 5. Target compounds 6 were then obtained by the reaction of 5 and substituted benzoic or cinnamic acid. Their structures were clearly verified by spectroscopic data (IR, 1H, 13C, and 31P NMR, and elemental analysis). These compounds were shown to be antivirally active in the bioassay. It was found that title compounds 6g, 6l, and 6n had the same inactivation effect of TMV (EC50 = 54.8, 60.0, and 65.2 μg/mL, respectively) as commercial product Ningnanmycin (EC50 = 55.6 μg/mL). To the best of our knowledge, this is the first report on the synthesis and antiviral activity of amide derivatives containing an α-aminophosphonate moiety.
