Design, synthesis, characterization, and antibacterial activity of {5-chloro-2-[(3-substitutedphenyl-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones

Premsai, Neithnadka; Venugopala, Katharigatta N.; Govender, Thavendran; Manuprasad, B. K.; Shashikanth, S.; Arunachalam, Pirama Nayagam

doi:10.1016/j.ejmech.2010.02.021

Cited by 96 publications

(25 citation statements)

References 33 publications

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“…The synthesis of intermediates 3a–3u was reported in supplementary file (Appendix S1) . The cyclization of appropriate amidoximes in the presence of chloroacetyl chloride and triethylamine afforded key intermediate 2 . Compounds 4a–4u were synthesized between 2 and 3a–3u .…”

Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of 1, 2, 4‐oxadiazole derivatives as novel GPR119 agonists

Xiang

Chen

et al. 2016

Chem Biol Drug Des

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A series of 1, 2, 4-oxadiazole derivatives have been designed and synthesized, and 25 compounds were evaluated their abilities by the assay of cAMP concentration in GPR119-transfected HEK293T cells. All compounds showed acceptable agonistic effects on GPR119. Among these compounds, 4p exhibited the best agonistic effects with the EC of 20.6 nm, which was comparable to that of positive control GPR119 agonist GSK1292263. The agonistic activity of these 1,2,4-oxadiazole derivatives led to the establishment of a structure-activity relationship.

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Section: Resultsmentioning

confidence: 99%

Synthesis and biological evaluation of 1, 2, 4‐oxadiazole derivatives as novel GPR119 agonists

Xiang

Chen

et al. 2016

Chem Biol Drug Des

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“…Hydrazone compounds bearing electron-withdrawing groups result in an improvement in their antimicrobial activities [8,9]. Rai and coworkers reported that a series of fluoro-, chloro-, bromo-, and iodosubstituted compounds have significant antimicrobial activities [10]. Vanadium complexes with Schiff bases and hydrazones have also been reported to have interesting antibacterial activities [11][12][13][14].…”

Section: Introductionmentioning

confidence: 99%

Synthesis, crystal structures, and antimicrobial activities of hydrazone complexes of vanadium(V)

Yao

Qiu

2015

Journal of Coordination Chemistry

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Two hydrazone ligands, (E)-N′-(3-bromo-2-hydroxybenzylidene)-2-methoxybenzohydrazide (HL a ) and (E)-N′-(2-hydroxy-3-methylbenzylidene)-2-methoxybenzohydrazide (HL b ), were prepared and characterized by IR, UV-vis, and 1 H NMR spectroscopy. The corresponding vanadium(V) complexes, 2[VOL a L]·CH 3 OH (1) and [VOL b L] (2), where L is the monoanionic form of benzohydroxamic acid (HL), were prepared and characterized by IR and UV-vis spectroscopy, and single-crystal X-ray diffraction. Complex 1 crystallizes as the monoclinic space group P2 1 /c, with unit cell dimensions a = 14.4161(16) Å, b = 14.0745(16) Å, c = 24.069(2) Å, β = 96.247(2), V = 4854.5(9) Å 3 , Z = 4, R 1 = 0.0541, wR 2 = 0.1423, Goof = 1.032. Complex 2 crystallizes in the orthorhombic space group Pbca, with unit cell dimensions a = 13.5906(6) Å, b = 18.1865(11) Å, c = 18.4068(11) Å, V = 4549.5(4) Å 3 , Z = 8, R 1 = 0.0549, wR 2 = 0.1397, Goof = 1.054. X-ray analysis indicates that the complexes are mononuclear octahedral vanadium(V) complexes. The thermal behavior of the complexes was investigated. The hydrazone ligands and their complexes were also evaluated for their antibacterial (Bacillus subtilis, Staphylococcus aureus, Escherichia coli, and Pseudomonas fluorescence) and antifungal (Candida albicans and Aspergillus niger) activities using the MTT (3-(4,5-*Corresponding author. dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide) assay. The two complexes have moderate to good activities against B. subtilis and S. aureus, and 1 has moderate activity against E. coli.

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“…4 Recently, a series of chloro, fluoro, iodo-and bromo-substituted compounds have been assayed for their remarkable antimicrobial activity. 5 Schiff base vanadium complexes have distinguish antibacterial activity. 6 In pursuit of new antimicrobial material, we report herein two new bromo-substituted hydrazone compounds N'-(3-bromo-2-hydroxybenzylidene)-3-hydroxy-4-methoxyben-zohydrazide (H 2 L 1 ), N'-(3-bromo-2-hydroxybenzylidene)-3,5-dimethoxybenzohydrazide (H 2 L 2 ), and their vanadium(V) complexes, [VOL 1 (OCH 3 )(CH 3 OH)] (1) and [VOL 2 (OCH 3 )(CH 3 OH)] (2), and studied their antimicrobial activities.…”

Section: Introductionmentioning

confidence: 99%

Vanadium(V) Complexes with Bromo-Substituted Hydrazones: Synthesis, Characterization, X-ray Crystal Structures and Antimicrobial Activity

Zhang¹,

Qiu²,

Liu³

2019

ACSi

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Two new V V complexes with the bromo-substituted hydrazones N'-(3-bromo-2-hydroxybenzylidene)-3-hydroxy-4-methoxybenzohydrazide (H 2 L 1), N'-(3-bromo-2-hydroxybenzylidene)-3,5-dimethoxybenzohydrazide (H 2 L 2), [VOL 1 (OCH 3)(CH 3 OH)] (1) and [VOL 2 (OCH 3)(CH 3 OH)] (2), were synthesized and structurally characterized by IR, UV-Vis and 1 H NMR spectroscopy, as well as single-crystal X-ray determination. The V atom in the mononuclear complexes are six-coordinated in octahedral geometry. The free hydrazones and the complexes were studied on their antibacterial activity on S. aureus, B. subtilis, E. coli and P. fluorescence, and antifungal activity on C. albicans and A. niger. The bromo groups of the hydrazone ligands may increase their antibacterial activity.

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Design, synthesis, characterization, and antibacterial activity of {5-chloro-2-[(3-substitutedphenyl-1,2,4-oxadiazol-5-yl)-methoxy]-phenyl}-(phenyl)-methanones

Cited by 96 publications

References 33 publications

Synthesis and biological evaluation of 1, 2, 4‐oxadiazole derivatives as novel GPR119 agonists

Synthesis and biological evaluation of 1, 2, 4‐oxadiazole derivatives as novel GPR119 agonists

Synthesis, crystal structures, and antimicrobial activities of hydrazone complexes of vanadium(V)

Vanadium(V) Complexes with Bromo-Substituted Hydrazones: Synthesis, Characterization, X-ray Crystal Structures and Antimicrobial Activity

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