Synthesis and Bioactivities of <i>α</i>-Aminophosphonate Derivatives Containing Benzothiazole and Thiourea Moieties

Liu, Jingzi; Song, Baoan; Bhadury, Pinaki S.; Hu, Deyu; Yang, Song

doi:10.1080/10426507.2011.575422

Cited by 26 publications

(5 citation statements)

References 20 publications

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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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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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“…Moreover, α ‐aminophosphonates are an important class of bioactive compounds. Many α ‐aminophosphonate derivatives have been found to possess extensive biological potentials, such as anticancer, antimicrobial, antiviral, cytotoxic, antitumor, antifungal, insecticidal and herbicidal activities . For examples, α ‐aminophosphonate with pyrazole and benzene structural characteristics (Fig.…”

Section: Introductionmentioning

confidence: 99%

“…Many -aminophosphonate derivatives have been found to possess extensive biological potentials, such as anticancer, antimicrobial, antiviral, cytotoxic, antitumor, antifungal, insecticidal and herbicidal activities. [20][21][22][23][24][25][26][27][28][29][30][31][32] For examples, -aminophosphonate with pyrazole and benzene structural characteristics ( Fig. 2, S), reported by Cao et al recently, possesses promising insecticidal activity against Plutella xylostella at 0.1 mg L −1 concentration and AChE inhibitory activity.…”

Section: Introductionmentioning

confidence: 99%

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

Wang

Zhu

et al. 2019

Pest Management Science

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BACKGROUND N‐Pyridylpyrazole derivatives have received continuous attention in agrochemical research during the last decade owing to their remarkable insecticidal or fungicidal potentials. To look for novel heterocyclic agrochemicals for increasing production of agriculture, a series of novel α‐aminophosphonate derivatives containing N‐pyridylpyrazole moiety were synthesized. RESULTS The structures of the title compounds were confirmed via melting point, IR, 1H NMR, 13C NMR, 31P NMR, HRMS and elemental analysis. The single crystal structure of diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(2,6‐dimethylphenylamino)methylphosphonate (compound 12b) was first reported. Moreover, the bioassays displayed that the title compounds exhibited modest or weak insecticidal activities against oriental armyworm at 200 μg mL−1. The first investigation on the fungicidal potential of chlorantraniliprole showed no significant activities towards the six tested fungi found in this study, however, most of the title compounds displayed apparent in vitro fungicidal activity against some plant fungi, in particular excellent activities towards Physalospora piricola. Compounds 11a and 11b had EC50 values of 18.8 and 17.4 μg mL−1, respectively, which were comparable with that of fungicide control triadimefon (EC50 = 24.7 μg mL−1) against Physalospora piricola. In addition, some compounds exhibited modest in vivo control efficacy at 0.5 mg mL−1 towards Sclerotinia sclerotiorum (11b: 30.1(±1.8)%), Rhizoctonia cerealis (11a: 20.4(±2.1)%; 11b: 30.2(±2.2)%), and Erysiphe graminis (11a: 30.3(±1.8)%; 12d: 40.2(±0.9)%). CONCLUSION Compounds 11a, 11b and 12d could be promising new lead structures for the development and discovery of novel fungicides towards Physalospora piricola and Erysiphe graminis. The structure‐activity relationship (SAR) analysis provided useful guidance and new understanding for the design of novel pyridylpyrazole‐containing agrochemicals. © 2019 Society of Chemical Industry

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“…Benzothiazole derivatives exhibit a wide variety of biological activities such as anticancer, 4 analgesic, 5 antiinflammatory, 6 anti-tubercular, 7 antimicrobial, 8 and insecticidal activity. 9 The compounds A and B (Figure 1) containing benzothiazole moiety possessed insecticidal activity against Prodenia litura and Plutella xylostella, respectively. 10,11 The compound C containing phenyl benzothiazole moiety showed acaricidal activity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and insecticidal activity of novel benzothiazole derivatives containing the coumarin moiety

Chen¹,

Wang²,

Wang³

et al. 2018

Arkivoc

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A series of novel benzothiazole derivatives containing a coumarin moiety was designed and synthesized. Their structures were characterized in detail via 1 H NMR, 13 C NMR, HRMS spectra and single-crystal X-ray diffraction analysis. The bioassay results indicated that some compounds showed encouraging insecticidal activity against Plutella xylostella and Aphis fabae at 400 mg/L. The preliminary structure-activity relationships were also discussed.

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

Cited by 26 publications

References 20 publications

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

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

One‐pot synthesis, structure and structure–activity relationship of novel bioactive diphenyl/diethyl (3‐bromo‐1‐(3‐chloropyridin‐2‐yl)‐1H‐pyrazol‐5‐yl)(arylamino)methylphosphonates

Synthesis and insecticidal activity of novel benzothiazole derivatives containing the coumarin moiety

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