anti-TMV Activity Research Articles

Design, Synthesis, and Antiviral Activity of α-Aminophosphonates Bearing a Benzothiophene Moiety

A series of α-aminophosphonates containing a benzothiophene moiety was designed and synthesized. All synthesized compounds were confirmed by 1H NMR, 13C NMR, 31P NMR, infrared spectroscopy, and elemental analysis. The half-leaf method was used to determine the in vivo efficacy of α-aminophosphonates bearing a benzothiophene moiety against the tobacco mosaic virus (TMV). Bioassay results showed that all compounds exhibited certain anti-TMV activity at 500 μg/mL concentration. Compound 2f exhibited a curative effect of up to 48.1% against TMV, which was almost similar to that obtained from the standard ningnanmycin (51.9%). [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text, figures, and tables.]

Design, Synthesis, and Antiviral Activity of α-Aminophosphonates Bearing a Benzothiophene Moiety

Abstract A series of α-aminophosphonates containing a benzothiophene moiety was designed and synthesized. All synthesized compounds were confirmed by 1H NMR, 13C NMR, 31P NMR, infrared spectroscopy, and elemental analysis. The half-leaf method was used to determine the in vivo efficacy of α-aminophosphonates bearing a benzothiophene moiety against the tobacco mosaic virus (TMV). Bioassay results showed that all compounds exhibited certain anti-TMV activity at 500 μg/mL concentration. Compound 2f exhibited a curative effect of up to 48.1% against TMV, which was almost similar to that obtained from the standard ningnanmycin (51.9%). [Supplementary materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfer, and Silicon and the Related Elements for the following free supplemental files: Additional text, figures, and tables.]

Synthesis and Antiviral and Fungicidal Activity Evaluation of β-Carboline, Dihydro-β-carboline, Tetrahydro-β-carboline Alkaloids, and Their Derivatives

Six known β-carboline, dihydro-β-carboline, and tetrahydro-β-carboline alkaloids and a series of their derivatives were designed, synthesized, and evaluated for their anti-tobacco mosaic virus (TMV) and fungicidal activities for the first time. All of the alkaloids and some of their derivatives (compounds 3, 4, 14, and 19) exhibited higher anti-TMV activity than the commercial antiviral agent Ribavirin both in vitro and in vivo. Especially, the inactivation, curative, and protection activities of alkaloids Harmalan (62.3, 55.1, and 60.3% at 500 μg/mL) and tetrahydroharmane (64.2, 57.2, and 59.5% at 500 μg/mL) in vivo were much higher than those of Ribavirin (37.4, 36.2, and 38.5% at 500 μg/mL). A new derivative, 14, with optimized physicochemical properties, obviously exhibited higher activities in vivo (50.4, 43.9, and 47.9% at 500 μg/mL) than Ribavirin and other derivatives; therefore, 14 can be used as a new lead structure for the development of anti-TMV drugs. Moreover, most of these compounds exhibited good fungicidal activity against 14 kinds of fungi, especially compounds 4, 7, and 11.

A New Phenolic Compound from the Leaves of Nicotiana tabacum and its Anti-tobacco Mosaic Virus Activities

A new phenolic compound, 5,(4-hydroxybutyl),2,3-dimethoxyphenol (1), was isolated from the leaves of Nicotiana tabacum. Its structure was elucidated by spectroscopic methods, including extensive 1D-NMR and 2D-NMR techniques. Compound 1 was also tested for its anti-tobacco mosaic virus (anti-TMV) activity and it showed high Anti-TMV activity with inhibition rate of 22.2 %.

A New Coumarin from Roots and Stems of Flue-Cured Tobacco and its Anti-Tobacco Mosaic Virus Activity

A new coumarin, 6-hydroxy-3-(4-hydroxyphenyl)-7-methoxy-2H-chromen-2-one (1), was isolated from the roots and stems of flue-cured tobacco (a variety of Nicotiana tabacum L). Its structure was elucidated by spectroscopic methods, including extensive 1D and 2D NMR techniques. Compound 1 was tested for its anti-tobacco mosaic virus (anti-TMV) activity and it shows potential anti-tobacco mosaic virus activity with inhibition rates of 23.6 %.

Synthesis and Anti-TMV Activity of Dialkyl/dibenzyl 2-((6-Substituted-benzo[d]thiazol-2-ylamino)(benzofuran-2-yl)methyl) Malonates

Starting from benzofuran-2-methanal, 6-substituted benzothiazole-2-amines and malonic esters, sixteen title compounds were designed and synthesized seeking to introduce anti-TMV activity. The structures of the newly synthesized compounds were confirmed by 1H-NMR, 13C-NMR, IR spectra, and MS (HREI) analysis. The bioassays identified some of these new compounds as having moderate to good anti-TMV activity. The compounds 5i and 5m have good antiviral activity against TMV with a curative rate of 52.23% and 54.41%, respectively, at a concentration of 0.5 mg/mL.

Isoflavanones from the Stem of Cassia siamea and Their Anti-tobacco Mosaic Virus Activities

Two new isoflavanones, (3R) 7,2',4'-trihydroxy-3'-methoxy-5-methoxycarbonyl-isoflavanone (1) and (3R) 7,2'-dihydroxy-3',4'-dimethoxy-5-methoxycarbonyl-isoflavanone (2), together with six known isoflavanones (3-8), were isolated from the stems of Cassia siamea. The structure of 1-8 was elucidated by spectroscopic methods including extensive 1D- and 2D-NMR techniques. Compounds 1, 2, 5-8 were evaluated for their anti-tobacco mosaic virus (Anti-TMV) activity. The results showed that compounds 1 and 6 showed potential anti-TMV activity with inhibition rates of 24.6% and 26.9%, respectively. Compounds 2, 5, 7, 8 also showed anti-TMV activity with inhibition rates in the range of 11.8-18.6%.

Two new flavonoids from the fruits of Ziziphus jujuba

Two new flavonoids, 8-formyl-3′,4′-dihydroxy-6,7-dimethoxyflavone (1) and 8-formyl-4′-hydroxy-3′,6,7- trimethoxyflavone (2), were isolated from the fruits of Ziziphus jujuba Mill. Their structures were elucidated on the basis of extensive NMR and MS means. The anti-tobacco mosaic virus (anti-TMV) and antioxidant activity of 1 and 2 were evaluated. They both showed anti-TMV activity with inhibition rates of 92.8% and 88.6%, and antioxidant activity with an IC50 value of 3.16 μg/mL and 3.87 μg/mL, respectively.

Three new xanthones from the stems of Garcinia oligantha and their anti-TMV activity

For more bioactive compounds, phytochemical investigations of the acetone extract of the stems of Garcinia oligantha resulted in the isolation of three new xanthones (1–3) and five known analogues (4–8). Structural elucidations of 1–3 were performed by spectral methods such as 1D and 2D (HMQC, HMBC, and ROESY) NMR spectroscopy, in addition to high resolution mass spectrometry. Compounds 1, 2, 6, 7, and 8 showed anti-tobacco mosaic virus (anti-TMV) activities with inhibition rates above 10%.

Three Novel Xanthones from Garcinia paucinervis and Their Anti-TMV Activity

Phytochemical investigations of the leaves of Garcinia paucinervis resulted in the isolation of three new xanthones 1–3 and five known analogues 4–8. Structural elucidations of 1–3 were performed by spectral methods such as 1D and 2D (HMQC, HMBC, and ROESY) NMR spectroscopy, in addition to high resolution mass spectrometry. Compounds 1–3 showed anti-TMV activities, with inhibition rates above 20%, especially for 1, which had a lower IC50 value of 21.4 µM.

Synthesis of tetrazole containing 1,2,3-thiadiazole derivatives via U-4CR and their anti-TMV activity

Abstract A series of novel tetrazole containing 1,2,3-thiadiazole derivatives were designed and synthesized via Ugi reaction. Their structures were confirmed by melting points, IR, 1H NMR, and HRMS (ESI). Preliminary bioassay indicated that most target compounds exhibited very good direct anti-TMV activity at 100 μg/mL, which was equal to or higher than that of ribavirin. Among them, compounds 4b, 4c and 4i also showed equivalent protection effect to ribavirin in vivo at 100 μg/mL.

Flavonoids from the bark and stems of Cassia fistula and their anti-tobacco mosaic virus activities

Two new flavonoids, fistulaflavonoids B and C (1–2), together with five known flavonoids (3–7) were isolated from the bark and stems of Cassia fistula. Their structures were determined by means of HRESIMS, extensive 1D and 2D NMR spectroscopic studies and chemical evidences. The anti-tobacco mosaic virus (anti-TMV) activity of the isolated flavonoids was also evaluated. The results showed that compounds 1 and 2 showed high anti-TMV activity with inhibition rate of 28.5% and 31.3%, which is higher than that of Ningnanmycin (24.7%). Compounds 4–7 showed modest anti-TMV activity with inhibition rate of 18.5%, 22.7%, 16.4%, and 15.3%, respectively.

Isoaurones from the Stem of Cassia siamea and Their Anti-Tobacco Mosaic Virus (Anti-TMV) Activity

Isoaurones from the Stem of Cassia siamea and Their Anti-Tobacco Mosaic Virus (Anti-TMV) Activity

New Urea and Thiourea Derivatives of Piperazine Doped with Febuxostat: Synthesis and Evaluation of Anti-TMV and Antimicrobial Activities

A series of new 4-(5-(3-cyano-4-isobutoxyphenyl)-4-methylthiazole-2-carbonyl)-N-(substituted phenyl)piperazine-1-carboxamides 8(a–e)/carbothioamides 8(f–j) were accomplished for biological interest by the simple addition of active functionalized arylisocyanates 7(a–e)/arylisothiocyanates 7(f–j) with 2-isobutoxy-5-(4-methyl-2-(piperazine-1-carbonyl)thiazol-5-yl)benzonitrile (4). Compound 4 was synthesized in high yields (94%) by the condensation reaction of febuxostat (1) with piperazine using a selective reagent such as propylphosphonic anhydride (T3P). Antiviral activity against Tobacco mosaic virus (TMV) and antimicrobial activity of the synthesized compounds were evaluated. Biological data revealed that 4-nitrophenyl substituted urea 8d, and 3-bromophenyl substituted thiourea 8f exhibited promising antiviral activities. Moreover, 4-fluorophenyl substituted urea 8a, 4-nitrophenyl substituted urea 8d, 3-bromophenyl substituted thiourea 8f, and 2,4-dichlorophenyl substituted thiourea 8j exhibited potent antimicrobial activity.

Isolation of Isoaurone from the Tobacco Stem and its Anti-tobacco Mosaic Virus Activity

A new isoaurone, 4,4'-dimethoxy-6-O-b -D-glucopyranosyl-isoaurone (1), were isolated from the tobacco stem. The structure of 1 was elucidated by spectroscopic methods including 1 D-and 2 D-NMR techniques. Compound 1 was also evaluated for its anti-tobacco mosaic virus (anti-TMV) activity and it showed high anti-tobacco mosaic virus activity with inhibition rate of 31.5 %. This valve is higher than that of positive control, ningnanmycin (28.4 %).

First Discovery and Stucture-Activity Relationship Study of Phenanthroquinolizidines as Novel Antiviral Agents against Tobacco Mosaic Virus (TMV)

A series of phenanthroquinolizidine alkaloids 1–24 were prepared and first evaluated for their antiviral activity against tobacco mosaic virus (TMV). The bioassay results showed that most of these compounds exhibited good to excellent in vivo anti-TMV activity, of which compounds 1, 2, 15 and 16 displayed significantly higher activity than (R)-antofine and commercial Ningnanmycin at the same test condition. The substituents on the phenanthrene moiety play an important role for maintaining high in vivo antiviral activity. The introduction of 6-hydroxyl, which is proposed to interact with TMV RNA, did increased anti-TMV activity. The 14aR-configuration was confirmed to be the preferred antiviral configuration for phenanthroquinolizidine alkaloids. Introduction of hydroxy group at 15-position of phenanthroquinolizidine alkaloids increased activity for S-configuration but decreased activity for R-configuration. Present study provides fundamental support for development and optimization of phenanthroquinolizidine alkaloids as potential inhibitors of plant virus.

Synthesis and bioactivity of N-tert-butyl-N′-acyl-5-methyl-1,2,3-thiadiazole-4-carbohydrazides

Abstract A series of novel N - tert -butyl- N ′-acyl-5-methyl-1,2,3-thiadiazole-4-carbohydrazides were designed and synthesized. Their structures were characterized by melting points, 1 H NMR, IR, ESI-MS, and elemental analysis. The bioassay tests indicated that compound 7o exhibited excellent direct anti-TMV activity and induction activity in vivo at 50 μg/mL, which was better than that of Ninamycin and tiadinial. Our studies indicated that 1,2,3-thiadiazole was an active substructure for novel pesticide development.

Antiviral Chromones from the Stem of Cassia siamea

Seven new chromones, siamchromones A-G (1-7), and 12 known chromones (8-19) were isolated from the stems of Cassia siamea. Compounds 1-19 were evaluated for their antitobacco mosaic virus (anti-TMV) and anti-HIV-1 activities. Compound 6 showed antitobacco mosaic virus (anti-TMV) activity with an inhibition rate of 35.3% and IC50 value of 31.2 μM, which is higher than that of the positive control, ningnamycin. Compounds 1, 10, 13, and 16 showed anti-TMV activities with inhibition rates above 10%. Compounds 4, 6, 13, and 19 showed anti-HIV-1 activities with therapeutic index values above 50.

Design, Synthesis, and Anti-tobacco Mosaic Virus (TMV) Activity of Phenanthroindolizidines and Their Analogues

On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of phenanthroindolizidines and their analogues 3-20 were designed, targeting tobacco mosaic virus (TMV) RNA, synthesized, and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds displayed good anti-TMV activity, and some of them exhibited higher antiviral activity than that of commercial Ningnanmycin (perhaps the most successful registered antiplant viral agent). Especially, (S)-deoxytylophorinine (5) with excellent anti-TMV activity (inactivation activity, 59.8%/500 μg mL(-1) and 40.3%/100 μg mL(-1); curative activity, 65.1%/500 μg mL(-1) and 43.7%/100 μg mL(-1); and protection activity, 70.2%/500 μg mL(-1) and 51.3%/100 μg mL(-1)) emerged as a potential inhibitor of the plant virus. Compound 20 exhibited a strong in vivo protection effect against TMV at 100 μg mL(-1), which indicated that phenanthroindolizidine analogues with a seven-membered D ring have a new and interesting structural scaffold and have great potential for further development as tobacco protection agents.

Design, Synthesis, and Antiviral Activity Evaluation of Phenanthrene-Based Antofine Derivatives

On the basis of our previous structure-activity relationship (SAR) and antiviral mechanism studies, a series of phenanthrene-based antofine derivatives (1-12 and 18-50) were designed targeting tobacco mosaic virus (TMV) RNA and synthesized and systematically evaluated for their antiviral activity against TMV. The bioassay results showed that most of these compounds exhibited good to excellent in vivo anti-TMV activity, of which compounds 19 and 27 displayed higher activity than commercial Ribavirin, thus emerging as potential inhibitors of plant virus. The novel concise structure provides another new template for antiviral studies.