Online citations, reference lists, and bibliographies.
← Back to Search

Design, Synthesis And Biological Evaluation Of Novel N-(4-([2,2′:5′,2′′-Terthiophen]-5-yl)-2-methylbut-3-yn-2-yl) Benzamide Derivatives

You-Quan Zhu, Zhang Hai-li, Wang Dan-yang, L. Li, H. Xu, Hua-bin Li, Y. Ma
Published 2015 · Chemistry

Cite This
Download PDF
Analyze on Scholarcy
Share
On the basis of the principle of combination of active groups, a series of novel N-(4-([2,2′:5′,2′′-terthiophen]-5-yl)-2-methylbut-3-yn-2-yl) benzamide derivatives were designed, synthesized and systematically evaluated for their antiviral activity against tobacco mosaic virus (TMV). The bioassay results showed that most of these compounds displayed good anti-TMV activity, and some of them exhibited higher antiviral activity than commercial Ningnanmycin. Especially, compound 8e with excellent anti-TMV activity (inactivation activity, 92.3%/500 µg·mL−1; curative activity, 85.7%/500 µg·mL−1 and protection activity, 64.7%/500 µg·mL−1) emerged as a potential inhibitor of plant virus TMV. Quantitative structure-activity relationship studies proved that the van der Waals volume (V) and electronic parameter (∑(∑σo+σp) and ∑σm) for the substituent R1 were very important for antiviral activities in this class of compounds.
This paper references
10.1016/J.JPHOTOBIOL.2007.05.006
The synthesis and photolarvicidal activity of 2,5-diarylethynylthiophenes.
Ren-Hai Wu (2007)
10.1016/0305-1978(81)90061-2
Mosquito larvicidal activity of polyacetylenes from species in the Asteraceae
T. Arnason (1981)
10.1021/JF062421R
Anti-tobacco mosaic virus (TMV) triterpenoid saponins from the leaves of Ilex oblonga.
Z. Wu (2007)
10.1126/science.177.4050.705
Broad-Spectrum Antiviral Activity of Virazole: 1-f8- D-Ribofuranosyl- 1,2,4-triazole- 3-carboxamide
R. Sidwell (1972)
10.1021/JF0709808
Inhibitory activity against tobacco mosaic virus (TMV) replication of pinoresinol and syringaresinol lignans and their glycosides from the root of Rhus javanica var. roxburghiana.
Ming-An Ouyang (2007)
10.1021/jf3013376
Design, synthesis, antiviral activity, and SARs of 14-aminophenanthroindolizidines.
Ziwen Wang (2012)
10.1021/jf803215t
Synthesis and antiviral activities of chiral thiourea derivatives containing an alpha-aminophosphonate moiety.
M. Chen (2009)
10.1021/jf802489e
Synthesis and antiviral activities of pyrazole derivatives containing an oxime moiety.
Guiping Ouyang (2008)
10.1016/j.jphotobiol.2009.06.002
The synthesis and photoactivated cytotoxicity of 2-methyl-4-oxo-3-prop-2-yn-1-ylcyclopent-2-en-1-yl-3-(2,2-dichlorovinyl)-2,2-dimethylcyclopropanecarboxylate conjugated with alpha-terthienyl derivatives.
N. Li (2009)
10.1016/0042-6822(83)90334-3
Human leukocyte interferon and the antiviral factor (AVF) from virus-infected plants stimulate plant tissues to produce nucleotides with antiviral activity.
M. Reichman (1983)
10.1021/JF0201677
Synthesis, fungicidal activity, and 3D-QSAR of pyridazinone-substituted 1,3,4-oxadiazoles and 1,3,4-thiadiazoles.
Xia-juan Zou (2002)
10.1111/j.1467-7652.2008.00322.x
3-Acetonyl-3-hydroxyoxindole: a new inducer of systemic acquired resistance in plants.
Y. Li (2008)
10.1016/J.CCLET.2010.07.011
Synthesis and anti-TMV activity of novel N-(pyrimidin-5-yl)-N′-phenylureas
De Kai Yuan (2011)
10.1007/BF01020259
Efficacy of the plant phototoxinα-terthienyl againstAedes intrudens and effects on nontarget organisms
B. J. Philogéne (2005)
10.1021/OL702467U
Molecular wires based on thienylethynylene: synthesis, photophysical properties, and excited-state lifetime.
J. Wang (2008)
10.1021/jf205362d
The limonoids and their antitobacco mosaic virus (TMV) activities from Munronia unifoliolata Oliv.
Yong-hui Ge (2012)
10.1007/s00726-007-0535-y
Antiviral activity of oxidized polyamines
U. Bachrach (2007)
10.1016/0048-3575(84)90015-4
Phototoxicity of the allelochemical, α-terthienyl, to larvae of Manduca sexta (L.) (Sphingidae)
K. Downum (1984)
10.1016/J.COPBIO.2005.02.009
Resistance to plant viruses: old issue, news answers?
C. Ritzenthaler (2005)
10.1021/JO034808O
Fast calculation of van der Waals volume as a sum of atomic and bond contributions and its application to drug compounds.
Y. Zhao (2003)
10.1007/s003740050413
Effects of marigold (Tagetes sp.) roots on soil microorganisms
E. Topp (1998)
10.1016/0261-2194(82)90002-3
Crop losses caused by viruses.
L. Bos (1982)
10.1021/BK-1995-0616.CH012
Fate of Phototoxic Terthiophene Insecticides in Organisms and the Environment
J. Arnason (1995)
10.1021/am301773t
[60]Fulleropyrrolidines bearing π-conjugated moiety for polymer solar cells: contribution of the chromophoric substituent on C₆₀ to the photocurrent.
C. Saravanan (2012)
10.1016/J.CCLET.2013.11.007
The synthesis and photoactivated cytotoxicity of novel 5-phenyl-3-(2,2′:5′,2″-terthien-5-yl)-4,5-dihydro-1H-pyrazolines
Z. Luo (2014)



Semantic Scholar Logo Some data provided by SemanticScholar