Synthesis and Bioactivities of α-Aminophosphonate Derivatives Containing Benzothiazole and Thiourea Moieties

• Published in: Phosphorus, sulfur, and silicon and the related elements Vol. 187; no. 1; pp. 61 - 70
• Main Authors: Liu, Jing-Zi, Song, Bao-An, Bhadury, Pinaki S., Hu, De-Yu, Yang, Song
• Format: Journal Article
• Language: English
• Published: ABINGDON Taylor & Francis Group 01.01.2012; Taylor & Francis
• Subjects: benzothiazole moiety; bioactivity; Chemistry; Chemistry, Inorganic & Nuclear; Chemistry, Organic; microwave irradiation; Physical Sciences; Science & Technology; synthesis; thiourea moiety; α-Aminophosphonate derivatives; synthesis; IN-VITRO; bioactivity; microwave irradiation; ANTITUMOR BENZOTHIAZOLES; FLUORINE; AGENTS; thiourea moiety; benzothiazole moiety; alpha-Aminophosphonate derivatives; ANTIVIRAL ACTIVITIES
• ISSN: 1042-6507; 1563-5325
• DOI: 10.1080/10426507.2011.575422

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.]