scholarly journals Design, Synthesis, and Bioactivity Evaluation of Novel Isoxazole-Amide Derivatives Containing an Acylhydrazone Moiety as New Active Antiviral Agents

Molecules ◽  
2019 ◽  
Vol 24 (20) ◽  
pp. 3766
Author(s):  
Zai-Bo Yang ◽  
Pei Li ◽  
Yin-Ju He
Keyword(s):  
Enzyme Activity ◽  
Mosaic Virus ◽  
Antiviral Agents ◽  
Plant Tolerance ◽  
Design Synthesis ◽  
Amide Derivatives ◽  
Induce Resistance ◽  
Antiviral Activities ◽  
Related Enzyme

As a continuation of our efforts to discover and develop “me-better” active molecules, in this study, a series of novel isoxazole-amide derivatives containing an acylhydrazone moiety were synthesized and evaluated for their antiviral activities against tobacco mosaic virus (TMV) and cucumber mosaic virus (CMV). Antiviral bioassays indicated that some of the target compounds exhibited better in vivo antiviral activities against TMV and CMV than those of Ningnanmycin (NNM). Especially, the compound 7t exhibited the best curative, protection, and inactivation activities against TMV and CMV which were superior to those of NNM. Meanwhile, our present work also revealed that compound 7t could enhance the defense-related enzyme activity and increase the chlorophyll content in tobacco leaves to induce resistance and enhance plant tolerance to TMV infection.

scholarly journals Novel Pyrazole-Hydrazone Derivatives Containing an Isoxazole Moiety: Design, Synthesis, and Antiviral Activity

Molecules ◽  
2018 ◽  
Vol 23 (7) ◽  
pp. 1798 ◽  
Author(s):  
Zaibo Yang ◽  
Pei Li ◽  
Xiuhai Gan
Keyword(s):  
Antiviral Activity ◽  
Tobacco Mosaic Virus ◽  
Mosaic Virus ◽  
Design Synthesis ◽  
Antiviral Activities ◽  
Protection Activity

In this study, a series of novel pyrazole-hydrazone derivatives containing an isoxazole moiety were synthesized. Antiviral bioassays indicated that some of the title compounds exhibited better in vivo antiviral activities against tobacco mosaic virus (TMV). In particular, compounds 6a, 6c and 6q exhibited the best curative activity, protection activity, and inactivation activity against TMV, respectively, which were superior to those of Ningnanmycin. This study demonstrated that this series of novel pyrazole-hydrazone derivatives containing an isoxazole amide moiety could effectively control TMV.

scholarly journals Design, Synthesis, and Biological Activity of Novel penta-1,4-dien-3-one Derivatives Containing a H-phosphonate Scaffold

2018 ◽  
Author(s):  
Lijuan Chen ◽  
Tao Guo ◽  
Rongjiao Xia ◽  
Xu Tang ◽  
Ying Chen ◽  
...  
Keyword(s):  
31P Nmr ◽  
Antiviral Agents ◽  
Antibacterial Activities ◽  
Effective Concentration ◽  
Xanthomonas Oryzae ◽  
Protective Activity ◽  
Design Synthesis ◽  
Xanthomonas Axonopodis ◽  
Antiviral Activities ◽  
Better Than

A series of penta-1,4-dien-3-one containing a H-phosphonate scaffold were designed and synthesized. The structures of all title compounds were determined by 1H-NMR, 13C-NMR, 31P-NMR, and HRMS. Bioassay results showed that several of the title compounds exhibited remarkable antibacterial and antiviral activities. Among these, compounds 3c and 3o exhibited substantial antibacterial activities against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac). In addition, compounds 3c, 3f, and 3r showed remarkable curative activities against tobacco mosaic virus (TMV), with 50% effective concentration (EC50) values of 290.0, 234.0, and 373.6 μg/mL, respectively. These were superior to that of ningnanmycin (386.2 μg/mL). Compound 3r exhibited comparative protective activity against TMV, with an EC50 value of 291.1 μg/mL, which was better than that of ningnanmycin (297.1 μg/mL). Notably, the solubility of all title compounds improved relative to the lead compound curcumin. These results suggest that penta-1,4-dien-3-one containing a H-phosphonate scaffold may be considered as an activator for antibacterial and antiviral agents.

scholarly journals Design, Synthesis, and Biological Activity of Novel Myricetin Derivatives Containing Amide, Thioether, and 1,3,4-Thiadiazole Moieties

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3132 ◽  
Author(s):  
Xianghui Ruan ◽  
Cheng Zhang ◽  
Shichun Jiang ◽  
Tao Guo ◽  
Rongjiao Xia ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Pathogenic Bacteria ◽  
Antibacterial Activities ◽  
Xanthomonas Oryzae ◽  
Design Synthesis ◽  
Antiviral Activities ◽  
Potential Alternative ◽  
Better Than

A series of myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties were designed and synthesized, and their antiviral and antibacterial activities were assessed. The bioassays showed that all the title compounds exhibited potent in vitro antibacterial activities against Xanthomonas citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the compounds 5a, 5f, 5g, 5h, 5i, and 5l, with EC50 values of 11.5–27.3 μg/mL, showed potent antibacterial activity against Xac that was better than the commercial bactericides Bismerthiazol (34.7 μg/mL) and Thiodiazole copper (41.1% μg/mL). Moreover, the in vivo antiviral activities against tobacco mosaic virus (TMV) of the target compounds were also tested. Among these compounds, the curative, protection, and inactivation activities of 5g were 49.9, 52.9, and 73.3%, respectively, which were better than that of the commercial antiviral Ribavirin (40.6, 51.1, and 71.1%, respectively). This study demonstrates that myricetin derivatives bearing amide, thioether, and 1,3,4-thiadiazole moieties can serve as potential alternative templates for the development of novel, highly efficient inhibitors against plant pathogenic bacteria and viruses.

Design, Synthesis and Evaluation of Thiourea Derivatives as Antimicrobial and Antiviral Agents

2019 ◽  
Vol 16 (6) ◽  
pp. 618-624 ◽  
Author(s):  
Veerasamy Ravichandran ◽  
Sivadasan Shalini ◽  
Krishnan Suresh Kumar ◽  
Harish Rajak ◽  
Ram Kishore Agrawal
Keyword(s):  
Spectral Analysis ◽  
Antimicrobial Agents ◽  
Antiviral Agents ◽  
Drug Resistant ◽  
Design Synthesis ◽  
Thiourea Derivatives ◽  
Structure Activity ◽  
Antiviral Activities ◽  
Anti Hiv

Background: The development of drug-resistant by bacteria appears rapidly and thus making the effectiveness of antibiotics severely limited. Methods: A series of thiourea derivatives was synthesized, characterized and evaluated for their in vitro antibacterial, antifungal and antiviral activities. Results: Structures of the newly synthesized compounds were confirmed by elemental and spectral analysis. The biological results showed that some of the target compounds displayed comparable antimicrobial and antiviral activities with reference drugs. Structure-activity relationship studies revealed that the ortho- chloro or fluoro substituted phenyl at Ar1 and substituted pyridinyl at Ar2 positions of the thiourea nucleus are essential for their in vitro antimicrobial and anti-HIV activity. In particular, compounds 8 and 10 showed better activity against the tested bacteria, fungi and viral strains than other synthesized PET derivatives reported in the present study. Conclusion: These results provide an encouraging lead that could be used for the development of new potent antiviral and antimicrobial agents

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

Molecules ◽  
2019 ◽  
Vol 24 (5) ◽  
pp. 925 ◽  
Author(s):  
Lijuan Chen ◽  
Tao Guo ◽  
Rongjiao Xia ◽  
Xu Tang ◽  
Ying Chen ◽  
...  
Keyword(s):  
31P Nmr ◽  
Dissociation Constants ◽  
High Resolution Mass Spectrometry ◽  
Antiviral Agents ◽  
Effective Concentration ◽  
Xanthomonas Oryzae ◽  
Design Synthesis ◽  
Microscale Thermophoresis ◽  
Antiviral Activities ◽  
Better Than

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.

Nitroxyl Modified Tobacco Mosaic Virus as a Metal-Free High-Relaxivity MRI and EPR Active Superoxide Sensor

2018 ◽  
Author(s):  
Madushani Dharmarwardana ◽  
André F. Martins ◽  
Zhuo Chen ◽  
Philip M. Palacios ◽  
Chance M. Nowak ◽  
...  
Keyword(s):  
Tobacco Mosaic Virus ◽  
Mosaic Virus ◽  
Single Molecule ◽  
Biological Fluids ◽  
Cellular Respiration ◽  
Organic Radical ◽  
Paramagnetic Resonance ◽  
Metal Free ◽  
Disease States

Superoxide overproduction is known to occur in multiple disease states requiring critical care yet non-invasive detection of superoxide in deep tissue remains a challenge. Herein, we report a metal-free magnetic resonance imaging (MRI) and electron paramagnetic resonance (EPR) active contrast agent prepared by “click conjugating” paramagnetic organic radical contrast agents (ORCAs) to the surface of tobacco mosaic virus (TMV). While ORCAs are known to be reduced <i>in vivo</i> to an MRI/EPR silent state, their oxidation is facilitated specifically by reactive oxygen species—in particular superoxide—and are largely unaffected by peroxides and molecular oxygen. Unfortunately, single molecule ORCAs typically offer weak MRI contrast. In contrast, our data confirm that the macromolecular ORCA-TMV conjugates show marked enhancement for <i>T<sub>1</sub></i> contrast at low field (<3.0 T), and <i>T<sub>2</sub></i> contrast at high field (9.4 T). Additionally, we demonstrated that the unique topology of TMV allows for “quenchless fluorescent” bimodal probe for concurrent fluorescence and MRI/EPR imaging, which was made possible by exploiting the unique inner and outer surface of the TMV nanoparticle. <a>Finally, we show TMV-ORCAs do not respond to normal cellular respiration, minimizing the likelihood for background, yet still respond to enzymatically produced superoxide in complicated biological fluids like serum.</a>

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