Research on antibacterial and antifungal agents. XI. Synthesis and antimicrobial activity of N-heteroaryl benzylamines and their Schiff bases

Fioravanti, Rossella; Biava, Mariangela; Porretta, Giulio Cesare; Landolfi, Carla; Simonetti, N; Villa, A.; Conte, Elisa; Porta-Puglia, A.

doi:10.1016/0223-5234(96)88217-1

Cited by 40 publications

(21 citation statements)

References 6 publications

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“…Various cobalt, nickel and copper metal complexes were reported to have antimicrobial activities (El-Ayaan and Abdel-Aziz, 2005;Sonmez et al, 2006). Schiff bases are characterized by the −N=CH− (imine) group which is important for elucidating the mechanism of transamination and racemisation reactions in biological systems (Lau et al, 1999) and are also known to have biological activities such as antimicrobial (Fioravanti et al, 1995;El-Masry et al, 2000;Pandeya et al, 1999), antifungal (Singh and Dash, 1998), antitumor (Desai et al, 2001) and herbicidal (Samadhiya and Halve, 2001). Schiff bases continue to occupy an important position as ligands in metal coordination chemistry (Wu et al, 2004;Aydogan et al, 2001), even almost a century since their discovery.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2′-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

Azam

Singh

Khokhra

et al. 2007

J. Zhejiang Univ. - Sci. B

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Abstract:Objective: A series of 2-benzylideneaminonaphthothiazoles were designed and synthesized incorporating the lipophilic naphthalene ring to render them more capable of penetrating various biomembranes. Methods: Schiff bases were synthesized by the reaction of naphtha[1,2-d]thiazol-2-amine with various substituted aromatic aldehydes. 2-(2'-Hydroxy)benzylideneaminonaphthothiazole was converted to its Co(II), Ni(II) and Cu(II) metal complexes upon treatment with metal salts in ethanol. All the compounds were evaluated for their antibacterial activities by paper disc diffusion method with Gram positive Staphylococcus aureus and Staphylococcus epidermidis and Gram negative Escherichia coli and Pseudomonas aeruginosa bacteria. The minimum inhibitory concentrations of all the Schiff bases and metal complexes were determined by agar streak dilution method. Results: All the compounds moderately inhibited the growth of Gram positive and Gram negative bacteria. In the present study among all Schiff bases 2-(2'-hydroxy)benzylideneaminonaphthothiazole showed maximum inhibitory activity and among metal complexes Cu(II) metal complex was found to be most potent. Conclusion: The results obtained validate the hypothesis that Schiff bases having substitution with halogens, hydroxyl group and nitro group at phenyl ring are required for the antibacterial activity while methoxy group at different positions in the aromatic ring has minimal role in the inhibitory activity. The results also indicated that the metal complexes are better antibacterial agents as compared to the Schiff bases.

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Section: Introductionmentioning

confidence: 99%

Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2′-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

Azam

Singh

Khokhra

et al. 2007

J. Zhejiang Univ. - Sci. B

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“…Schiff bases are well known not only for thermochromism and photochromism in the solid state but also for their pharmacological properties as antibacterial agents, antifungal bioactivities, and antitumor and inhibitory activities against viruses . In particular, much attention has been paid on heterocyclic Schiff base because of its super biological activity .…”

Section: Introductionmentioning

confidence: 99%

Syntheses, Characterization, and Antibacterial Activities of Four New Schiff Base Compounds Derived from 1‐Phenyl‐3‐methyl‐4‐benzoyl‐2‐pyrazolin‐5‐one

Liu

Yuan

Liu

et al. 2012

Journal of Heterocyclic Chem

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Four new Schiff bases were designed and synthesized. 5‐Methyl‐4‐(4‐aminophenylamino‐phenyl‐methylene)‐2‐phenyl‐2,4‐dihydro‐pyrazol‐3‐one (compound 1) and 5‐methyl‐4‐(2‐aminophenylamino‐phenyl‐methylene)‐2‐phenyl‐2,4‐dihydro‐pyrazol‐3‐one (compound 2) were synthesized by interaction of 1‐phenyl‐3‐methyl‐4‐benzoyl‐2‐pyrazolin‐5‐one (PMBP) with o‐ and p‐phenylenediamine, respectively; 4,4′‐(1,2‐phenylenebis(azanediyl)bis(phenylmethanylylidene))bis(3‐methyl‐1‐phenyl‐1H‐pyrazol‐5(4H)‐one) (compound 3) and 5‐methyl‐4‐(phenyl(2‐((3‐phenylallylidene)amino)phenylamino)methylene)‐2‐phenyl‐2,4‐dihydro‐pyrazol‐3‐one (compound 4) were synthesized by interaction of compound 2 with PMBP and cinnamaldehyde in an ethanolic medium, respectively. The molecular structures of the title compounds were first characterized by single‐crystal X‐ray diffraction, mass spectrometry, and elemental analysis. The title compounds were tested for antibacterial activity (Escherichia coli, Staphylococcus aureus, and Bacillus subtilis) by disk diffusion method.

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“…Our previous studies (Li et al 2002) showed that the antimicrobial activity of organoselenium compounds is many times higher than that of sulfur and oxygen analogues having isosteric elements. Schiff base compounds have been used in several areas (Fioravanti et al 1995;Metri et al 1995) for their antiviral, anti-inflammatory and antioxidative activity. (2-Hydroxybenzimido) ethyl-n-hexylselenide ( Figure 1) is a kind of selenium-containing Schiff base compound or a Schiff-base-group-containing selenide (Schiff base selenide).…”

Section: Introductionmentioning

confidence: 99%

Absorption and fluorescence study of the interaction between (2-hydroxy-benzimido)ethyl-n-hexylselenide and bovine serum albumin

Yang

Liu

et al. 2004

Journal of Pharmacy and Pharmacology

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The binding of Schiff base selenide, (2-hydroxy-benzimido)ethyl-n-hexylselenide, to bovine serum albumin (BSA) was studied using fluorescence spectroscopy. The measurement was performed in Tris-HCl buffer aqueous medium at pH 7.4. Stern-Volmer graphs were plotted and quenching constants were estimated. The quenching constant at 303 K was (1.639 +/- 0.046) x 10(13) L mol(-1) s(-1). Decreased quenching was observed as temperature increased, but at the temperature range of 303-313 K, the association of Schiff base selenide to BSA was not significantly different. The static quenching presented in the system of Schiff base selenide and BSA. A complex was possibly formed between Schiff base selenide and BSA, which was responsible for the quenching of the fluorescence of BSA. This fact was also confirmed by differences in the absorption spectra of BSA before and after Schiff base selenide addition. The hydrophobic interaction was found to play a main role in the binding according to the thermodynamic parameters, enthalpy change (DeltaH) and entropy change (DeltaS) of reaction. Schiff base selenide most likely binds to the hydrophobic pockets within sub domain IIA of BSA, which can be proved by competition experiments for sodium dodecyl sulfate. By constant-wavelength synchronous fluorescence spectra, the influence of (2-hydroxy-benzimido)ethyl-n-hexylselenide on the surrounding environment of tyrosine and tryptophan residues in BSA was also investigated. The red shift of the fluorescence peak of tryptophan residues indicated that the hydrophobic amino acid structure surrounding tryptophan residues in BSA collapsed slightly after the addition of (2-hydroxy-benzimido)ethyl-n-hexylselenide.

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Research on antibacterial and antifungal agents. XI. Synthesis and antimicrobial activity of N-heteroaryl benzylamines and their Schiff bases

Cited by 40 publications

References 6 publications

Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2′-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

Synthesis of Schiff bases of naphtha[1,2-d]thiazol-2-amine and metal complexes of 2-(2′-hydroxy)benzylideneaminonaphthothiazole as potential antimicrobial agents

Syntheses, Characterization, and Antibacterial Activities of Four New Schiff Base Compounds Derived from 1‐Phenyl‐3‐methyl‐4‐benzoyl‐2‐pyrazolin‐5‐one

Absorption and fluorescence study of the interaction between (2-hydroxy-benzimido)ethyl-n-hexylselenide and bovine serum albumin

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