Synthesis and characterization of novel substituted N-benzothiazole-2-yl-acetamides

Sakarya, Handan; Görgün, Kamuran; Öğretır, Cemi̇l

doi:10.1016/j.arabjc.2012.02.008

Cited by 6 publications

(7 citation statements)

References 13 publications

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“…Then it was hydrolyzed in water and extracted with EtOAc. Powders of the compounds ( 7 – 9 ) were obtained after drying with Na 2 SO 4 [ 33 ]. The physical properties of the synthesized compounds are presented in Additional file 1 : Table S1.…”

Section: Methodsmentioning

confidence: 99%

“…A solution of acetophenonethiazole (0.4 g, 2.3 mmol) and p -nitrobenzaldehyde (0.34 g, 2.3 mmol), and p -nitroacetophenone thiazole (0.3 g, 13.5 mmol) and p -nitrobenzaldehyde (0.205 g, 13.5 mmol) (Scheme 1 , Path c ) [ 34 ] were mixed in absolute ethanol (30 mL) and refluxed for 4 h in the presence of 15% ZnO nanoparticles load at 78 °C for compounds 10 and 11 , respectively. The mixture was poured into 150 mL of crushed ice, while stirring with glass road and powders obtained were washed with cold ethanol and diethyl ether to remove unreacted amine, aldehyde and its derivatives [ 33 ] (Scheme 1 ) . The physical properties of the synthesized compounds are presented in Additional file 1 : Table S1.…”

Section: Methodsmentioning

confidence: 99%

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Synthesis, antibacterial and antioxidant activities of Thiazole-based Schiff base derivatives: a combined experimental and computational study

et al. 2021

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Background Thiazole-based Schiff base compounds display significant pharmacological potential with an ability to modulate the activity of many enzymes involved in metabolism. They also demonstrated to have antibacterial, antifungal, anti-inflammatory, antioxidant, and antiproliferative activities. In this work, conventional and green approaches using ZnO nanoparticles as catalyst were used to synthesize thiazole-based Schiff base compounds. Results Among the synthesized compounds, 11 showed good activities towards Gram-negative E. coli (14.40 ± 0.04), and Gram-positive S. aureus (15.00 ± 0.01 mm), respectively, at 200 μg/mL compared to amoxicillin (18.00 ± 0.01 mm and 17.00 ± 0.04). Compounds 7 and 9 displayed better DPPH radical scavenging potency with IC50 values of 3.6 and 3.65 μg/mL, respectively, compared to ascorbic acid (3.91 μg/mL). The binding affinity of the synthesized compounds against DNA gyrase B is within − 7.5 to − 6.0 kcal/mol, compared to amoxicillin (− 6.1 kcal/mol). The highest binding affinity was achieved for compounds 9 and 11 (− 6.9, and − 7.5 kcal/mol, respectively). Compounds 7 and 9 displayed the binding affinity values of − 5.3 to − 5.2 kcal/mol, respectively, against human peroxiredoxin 5. These values are higher than that of ascorbic acid (− 4.9 kcal/mol), in good agreement with the experimental findings. In silico cytotoxicity predictions showed that the synthesized compounds Lethal Dose (LD50) value are class three (50 ≤ LD50 ≤ 300), indicating that the compounds could be categorized under toxic class. Density functional theory calculations showed that the synthesized compounds have small band gap energies ranging from 1.795 to 2.242 eV, demonstrating that the compounds have good reactivities. Conclusions The synthesized compounds showed moderate to high antibacterial and antioxidant activities. The in vitro antibacterial activity and molecular docking analysis showed that compound 11 is a promising antibacterial therapeutics agent against E. coli, whereas compounds 7 and 9 were found to be promising antioxidant agents. Moreover, the green synthesis approach using ZnO nanoparticles as catalyst was found to be a very efficient method to synthesize biologically active compounds compared to the conventional method.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Synthesis, antibacterial and antioxidant activities of Thiazole-based Schiff base derivatives: a combined experimental and computational study

et al. 2021

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“…This band may be assigned to a 2 B 1g → 2 A 1g transition, characteristic for a distorted octahedral structure. 19 In addition, the complexes of Co(II) and Ni(II) exhibited two bands at 14684 and 16977 cm -1 and at 9354 and 10405 cm -1 , assigned to 4 T 1g (F)→ 4 A 2g (F), 4 T 1g (F)→ 4 T 2g (F) and 3 A 2g (F)→ 3 T 2g (F), 3 A 2g (F)→ 3 T 1g (F) transitions, respectively, suggesting octahedral coordination. The copper(II) complex of HL 4 shows a band at 12650 cm -1 , assignable to a 2 B 1g → 2 A 1g transition, characteristic for a distorted square-planar geometry.…”

Section: Electronic Absorption Spectramentioning

confidence: 99%

“…Besides the chelating ability of Schiff bases of heterocyclic com-pounds containing 5-and 6-membered rings, they also find potential applications in the field of therapeutics. 1 Benzothiazole is a privileged bicyclic ring system with significant biological properties, such as antimicrobial [2][3][4][5] and anticancer. 6 Transition metal complexes of Schiff bases of 2-amino-6-nitrobenzothiazole enabled a study of the different ligation behaviors of Schiff bases.…”

Section: Introductionmentioning

confidence: 99%

Spectral, NLO and antimicrobial studies of Co(II), Ni(II) and Cu(II) complexes of Schiff base ligands of 2-amino-6-nitrobenzothiazole

Kanagavalli¹,

Sankarganesh²,

Raja³

et al. 2019

JSCS

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Novel series of Co(II), Ni(II) and Cu(II) transition metal complexes were synthesized from the Schiff base ligands HL 1-HL 4 derived from 2-amino-6nitrobenzothiazole with various aromatic aldehydes, i.e., 4-methylbenzaldehyde, 4ethylbenzaldehyde, 2-hydroxybenzaldehyde and 4-hydroxybenzaldehyde, respectively. The ligands HL 1-HL 4 and their metal (II) complexes were characterized by atomic absorption spectroscopy (AAS), magnetic susceptibility and molar conductance measurements, and UV-Vis, FT-IR and NMR spectroscopic techniques. The spectroscopic studies revealed that the complexes of HL 1-HL 3 coordinated in an octahedral environment and L 4 in square planar/tetrahedral geometry. The ligands HL 1-HL 4 and their metal(II) complexes were screened for their antimicrobial activities against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa and Candida albicans. The results suggest that the complexes of HL 4 possess greater inhibition activity towards C. albicans. The nonlinear optics (NLO) activities of ligands HL 1-HL 4 were determined. The obtained results showed that ligands HL 1 and HL 2 have greater second harmonic generation (SHG) efficiency than HL 3 and HL 4 .

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“…FT-IR spectra [20] of (M 14 ) showed characteristic absorption bands at (3421-3326 cm -1 ) and (1512-1330 cm -1 ) due to (NH 2 ) in thiazole ring and (NO 2 ) asymmetric and symmetric respectively.…”

Section: Synthesis 2-aminobenzothiazole Substitutes (M1-m14)mentioning

confidence: 99%

Synthesis, Characterization and Biological Activity Evaluation of Some New Azo Derivatives from 2- Amino Benzothiazole and Their Derivatives

Ahmed¹,

Jebur²,

Hamzah³

2018

KUJSS

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Synthesis and characterization of novel substituted N-benzothiazole-2-yl-acetamides

Cited by 6 publications

References 13 publications

Synthesis, antibacterial and antioxidant activities of Thiazole-based Schiff base derivatives: a combined experimental and computational study

Synthesis, antibacterial and antioxidant activities of Thiazole-based Schiff base derivatives: a combined experimental and computational study

Spectral, NLO and antimicrobial studies of Co(II), Ni(II) and Cu(II) complexes of Schiff base ligands of 2-amino-6-nitrobenzothiazole

Synthesis, Characterization and Biological Activity Evaluation of Some New Azo Derivatives from 2- Amino Benzothiazole and Their Derivatives

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