Synthesis and insecticidal assessment of some innovative heterocycles incorporating a thiadiazole moiety against the cotton leafworm, Spodoptera littoralis

Fadda, Ahmed A.; Salam, Mustafa Abdul; Tawfik, Eman H.; Anwar, E. M.; Etman, H. A.

doi:10.1039/c7ra06087d

Cited by 28 publications

(17 citation statements)

References 31 publications

(33 reference statements)

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“…As a continuation of our interest in the chemistry of cyanoacetamide [20–22,31–37], N , N ′, N ″, N ‴‐(5,10,15,20‐tetraphenylporphyrin‐2,7,12,17‐tetrayl)tetrakis(2‐cyanoacetamide) ( 8 ) was achieved by heating compound 7 with cyanoacetic acid in presence of drops of acetic anhydride. The structure of 8 was elucidated by spectroscopic data.…”

Section: Resultsmentioning

confidence: 99%

“…Moreover, cyanoacetamide derivatives are considered one of the most significant starting materials for the synthesis of different heterocyclic derivatives [20–22]. From these above facts and in continuation to our interest in developing an attractive, and alternative synthesis of mono(heteroaryl)tetraphenyl porphyrin through the reaction of β‐cyanoacetamide moiety in compound 8 with bifunctional reagents and evaluation of their biological activity as antitumor reagents.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Masaret

2021

Journal of Heterocyclic Chem

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A new methodology for the synthesis of some new β‐porphyrin heterocyclic compounds containing nitrogen derivatives 10, 12, 13, 15, 17, 19, 21, 22, 25, 27, and 29 was screened for their cytotoxic activities. Both elemental and spectral analyses were used to confirm the structures of new compounds. Compounds 22, 27, and 21 exhibited very strong activity against the HepG2 cell line. Investigation of the binding between porphyrin 22 and the binding site of telomerase was performed by molecular docking.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Masaret

2021

Journal of Heterocyclic Chem

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“…A class of heterocyclic azo dyes is the thiazolylazo dye. Thiazoles are an important class of heterocyclic compounds which are related with many types of biological properties, probably by virtue of the -N=C-S− group, these include insecticidal, herbicidal, anti-oxidant, -bacterial, -convulsant and -inflammatory [29] [30] [31] [32] [33]. Thiazoles are readily capable of crossing cellular membranes owing to their better liposolubility, attributed to the presence of a sulphur atom [32].…”

Section: Introductionmentioning

confidence: 99%

“…Thiazoles are an important class of heterocyclic compounds which are related with many types of biological properties, probably by virtue of the -N=C-S− group, these include insecticidal, herbicidal, anti-oxidant, -bacterial, -convulsant and -inflammatory [29] [30] [31] [32] [33]. Thiazoles are readily capable of crossing cellular membranes owing to their better liposolubility, attributed to the presence of a sulphur atom [32]. The thiazole ring is present in several potent pharmacologically active molecules such as sulfathiazole (an antimicrobial drug), ritonavir (an antiretroviral drug) and abafungin (an antifungal drug) [34].…”

Section: Introductionmentioning

confidence: 99%

Syntheses, Characterization and Biological Activity of Novel Thiazoylazo Dye and Its Coordination Compounds

Aiyelabola¹

2021

ABC

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The present work describes the synthesis of a novel heterocyclic azo dye by general diazonization of 2-amino-4,5-dimethylthiazole followed by the diazocoupling of the resulting diazonium ion with 5-methyl-2-(propan-2-yl)phenol to obtain ligand L. This was characterized using Fourier-transformed infrared and electronic spectrophotometry. Ligand L was further coordinated with five metal ions, M:L, 1:2 [M = Cu(II), Mn(II), Zn(II), Ni(II) and Co(II)]. The coordination compounds obtained were characterized by electronic, IR spectrophotometry, magnetic susceptibility and percentage metal analyses. The results obtained suggested that a thiazoylazo dye was obtained as ligand L. It was proposed that two molecules of the solvent coordinated to the metal ion in addition with the ligands to give an octahedral geometry for copper(II), manganese(II) and nickel(II) complexes. On the other hand, square planar geometry was suggested for zinc(II) and cobalt(II) complexes. The anti-inflammatory activity of the ligand and coordination compounds was evaluated using four in vitro-based assays viz: xanthine oxidase and lipoxygenase inhibition assay, membrane stability and protein denaturation assay. The synthesized compounds generally exhibited good anti-inflammatory activity in all the assays carried out. However, the reference standards, in this instance, were more effective in the case of xanthine oxidase, lipoxygenase and protein denaturation inhibitory assays. For the membrane stability study, the coordination compounds and ligand L elicited more potent anti-inflammatory activity than the standard drug.

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“…reported that introduction of a 1,3,4‐oxadiazole ring into target compounds could change their polarity, binding affinity with their receptor and flexibility, effectively enhancing their bioactivity . Furthermore, thiophene groups constitute a class of scaffold in bioactive molecules that are related to a variety of activities including antifungal, antimicrobial, insecticidal and herbicidal . Over the past few years, the synthesis and bioactivity of thiophene derivatives have attracted considerable attention and some representative examples of thiophene‐derived compounds are known for their ability to protect certain plants against severe diseases …”

Section: Introductionmentioning

confidence: 99%

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

Wen

Jian

Shang

et al. 2018

Pest Management Science

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BACKGROUND Natural stilbenes (especially resveratrol and its derivatives) are well‐known phytoalexins that are active against many plant diseases. However, oxidative degradation and low bioavailability limit their exogenous application as fungicides on crops. In this study, a new class of resveratrol‐inspired thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit was synthesized and the derivatives' antifungal activities against phytopathogenic fungi were investigated. RESULTS The results revealed that compounds 5h and 5j exhibited improved antifungal activity against Botrytis cinerea with median effective concentrations (EC50) of 168.5 and 155.4 µg mL−1, respectively, which were superior to the EC50 of resveratrol (263.1 µg mL−1). Compound 5j was shown to effectively control disease development in B. cinerea‐infected tomatoes in vivo. Notably, considerably abnormal mycelial morphology and increased cell membrane conductivity were observed in the presence of compound 5j. CONCLUSION A new class of thiophene‐containing stilbene derivatives was designed and synthesized. Bioassay results showed that compound 5j exhibited promising antifungal activity, suggesting practical potential for fungal disease control. © 2018 Society of Chemical Industry

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Synthesis and insecticidal assessment of some innovative heterocycles incorporating a thiadiazole moiety against the cotton leafworm, Spodoptera littoralis

Abstract: A new 2-cyano-N-(5-ethyl-1,3,4-thiadiazol-2-yl)acetamide was utilized as a versatile precursor for the synthesis of various heterocycles.

Cited by 28 publications

References 31 publications

Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Synthesis, biological evaluation, and docking studies of various β‐substituted porphyrin conjugates embedded with N‐containing heterocycles

Syntheses, Characterization and Biological Activity of Novel Thiazoylazo Dye and Its Coordination Compounds

Synthesis and antifungal activities of novel thiophene‐based stilbene derivatives bearing an 1,3,4‐oxadiazole unit

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