Synthesis and herbicidal activity evaluation of novel α-amino phosphonate derivatives containing a uracil moiety

Che, Jian-Yi; Xu, Xinguang; Tang, Zilong; Gu, Yu‐Cheng; Shi, De‐Qing

doi:10.1016/j.bmcl.2016.01.010

Cited by 39 publications

(13 citation statements)

References 21 publications

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“…α-Aminophosphonic acid derivatives have demonstrated to be useful substrates as enzyme inhibitors in proteolysis processes and, consequently, they show an assorted biological activity. [1] In fact, numerous α-aminophosphonic acid derivatives display activity as agrochemicals, [2] as well as antimicrobial, [3] antioxidant [4] or anticancer agents, [5] and show promising biological properties for the treatment of infectious diseases ( Figure 2). [6] α-Aminophosphonic acids are often obtained from the hydrolysis of their phosphonate esters and, for this reason, the synthesis of α-aminophosphonates is an important task in organic chemistry.…”

Section: Introductionmentioning

confidence: 99%

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

et al. 2020

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A wide range of methods for the enantioselective synthesis of α‐aminophosphonic acid derivatives have been developed over the years. Although the most used methodology is the Pudovik reaction, the use of α‐iminophosphonates for the synthesis of optically active α‐aminophosphonates has emerged during the last years. The existing methods for the synthesis of α‐phosphorylated imines and their enantioselective reactions for the synthesis of enantio‐enriched α‐aminophosphonates are summarized in this review.

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Section: Introductionmentioning

confidence: 99%

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

et al. 2020

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“…Due to their outstanding biological and physical characteristics together with their usefulness as intermediates in synthesis; AAPs have found a wide variety of applications in industry, agriculture and medicine (Moonen et al, 2004;Palacios et al, 2004;Schug and Lindner, 2005). They are discovered to be antibacterial (Subramanyam et al, 2017), antifungal (Yang et al, 2006), antiviral (Xu et al, 2006), anti-inflammatory agents (Sujatha et al, 2017), anti-HIV (Bhattacharya et al, 2012), anticancer (Bahrami et al, 2016), anti-proliferative and apoptosis inducing (Huang et al, 2016a(Huang et al, , 2016bLi et al, 2015), antitumor (Liu et al, 2017), herbicidal activity (Che et al, 2016) and insecticidal activity (Jiang et al, 2013;Liu et al, 2012). Addition of trialkyl or dialkylphosphite to imines is a successful technique to obtain them (Azizi et al, 2004;Heydari et al, 2009;Kassaee et al, 2009;Manjula et al, 2013;Yadav et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

Ultrasound-promoted solvent-free synthesis of some new α-aminophosphonates as potential antioxidants

Basha¹,

Subramanyam²,

Rao³

2020

Main Group Metal Chemistry

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Ultrasonic irradiation has been adopted in order to achieve an efficient synthesis of some novel α-aminophosphonates by Pudovik reaction. Major benefits of this method are as follows: eco-friendly, free of catalyst, high yielding, uncomplicated work-up procedure, short reaction time, and solvent free condition. Spectral characterisation and elemental analysis of the synthesized samples was carried out. In vitro antioxidant activity of the title compounds was screened by DPPH˙, O2-˙ and NO˙ scavenging methods. Good activity was shown by most of the compounds as compared with the standards.

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“…Phosphonates and their immediate derivatives possess a wide range of biological activities [19,20,21,22,23,24,25] and are, therefore, widely employed as plant virucides (Figure 1b), bactericides, fungicides, herbicides (Figure 1c), and plant growth regulators. Because the phosphorus–carbon bond of phosphonate derivatives is not susceptible to enzymatic degradation, they possess improved cell permeability, a lipophilic nature, and good physiological stability [26,27]. In a previous study from our group, we synthesized a series of phosphorylated flavonoid derivatives (Figure 2), most of which exhibited excellent antibacterial activities [21,28].…”

Section: Introductionmentioning

confidence: 99%

Novel Phosphorylated Penta-1,4-dien-3-one Derivatives: Design, Synthesis, and Biological Activity

et al. 2019

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A series of novel phosphorylated penta-1,4-dien-3-one derivatives were designed and synthesized. The structures of all title compounds were determined by 1H-NMR, 13C-NMR, 31P-NMR, and high-resolution mass spectrometry (HRMS). Bioassay results showed that several of the title compounds exhibited remarkable antibacterial and antiviral activities. Among these, compound 3g exhibited substantial antibacterial activity against Xanthomonas oryzae pv. Oryzae (Xoo), with a 50% effective concentration (EC50) value of 8.6 μg/mL, which was significantly superior to bismerthiazol (BT) (58.8 µg/mL) and thiodiazole-copper (TC) (78.7 μg/mL). In addition, compound 3h showed remarkable protective activity against tobacco mosaic virus (TMV), with an EC50 value of 104.2 μg/mL, which was superior to that of ningnanmycin (386.2 μg/mL). Furthermore, the microscale thermophoresis and molecular docking experiments on the interaction of compounds 3h and 3j with TMV coat protein (TMV CP) were also investigated. Compounds 3h and 3j bound to TMV CP with dissociation constants of 0.028 and 0.23 μmol/L, which were better than that of ningnanmycin (0.52 μmol/L). These results suggest that novel phosphorylated penta-1,4-dien-3-one derivatives may be considered as an activator for antibacterial and antiviral agents.

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Synthesis and herbicidal activity evaluation of novel α-amino phosphonate derivatives containing a uracil moiety

Cited by 39 publications

References 21 publications

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

α‐Iminophosphonates: Useful Intermediates for Enantioselective Synthesis of α‐Aminophosphonates

Ultrasound-promoted solvent-free synthesis of some new α-aminophosphonates as potential antioxidants

Novel Phosphorylated Penta-1,4-dien-3-one Derivatives: Design, Synthesis, and Biological Activity

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