1038997-72-6Relevant articles and documents
Synthesis and bioactivities of α-aminophosphonate derivatives containing benzothiazole and thiourea moieties
Liu, Jing-Zi,Song, Bao-An,Bhadury, Pinaki S.,Hu, De-Yu,Yang, Song
, p. 61 - 70 (2012/04/10)
The synthesis of a series of novel α-aminophosphonate derivatives containing benzothiazole and thiourea moieties from substituted 2-aminobenzothiazoles and synthetic intermediates O,O'-dialkylisothiocyanat- (phenyl)methylphosphonates under microwave irradiation has been demonstrated. Several salient features, such as good to excellent yields, shorter reaction times, milder reaction conditions, and simple purification procedures, make the present synthetic protocol highly attractive to access the title compounds. Bioassays indicated that most of the compounds possessed broad-spectrum insecticidal and antiviral activities against Tobacco Mosaic Virus (TMV) in vivo. Interestingly, in comparison with control insecticide Avermectin, two compounds displayed remarkably high in vitro insecticidal activities against Plutella xylostella. Furthermore, according to the results from preliminary bioassay, all were associated with moderate to good anti-TMV activities. [Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements for the following free supplemental resource: Tables S1-S4. Figures S1-S52.] Copyright Taylor and Francis Group, LLC.
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.