Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine

Pandeya, S. N.; Sriram, D.; Nath, Gopal; Clercq, Erik De

doi:10.1016/s0014-827x(99)00075-0

Cited by 332 publications

(249 citation statements)

References 2 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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“…Isatin also exhibits other biological activities, such as anticonvulsant, cytotoxic, antifungal etc. Isatin and its analogs are versatile substrates, which can be used for the synthesis of numerous heterocyclic compounds Sridhar & Sreenivasulu, 2001;Sarangapani & Reddy, 1994;Varma et al, 2004;Pandeya et al, 1999;Aboul-Fadl et al, 2010). In our work, we are interested in developing a new 5-bromoisatin and continuing the research work of Qachchachi to explore other applications (Qachchachi et al, 2013(Qachchachi et al, , 2014Kharbach et al, 2016).…”

Section: Structure Descriptionmentioning

confidence: 99%

5-Bromo-1-methylindoline-2,3-dione

Kharbach¹,

Haoudi²,

Capet

et al. 2016

IUCr Data

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In the title compound, C 9 H 6 BrNO 2 , the indoline ring system, the two ketone O atoms and the Br atom are nearly coplanar, with the largest deviation from the mean plane being À0.1025 (4) Å . In the crystal, molecules are linked by two weak C-HÁ Á ÁO hydrogen bonds and -interactions [inter-centroid distance = 3.510 (2) Å ], forming a three-dimensional structure. Structure descriptionIsatin derivatives have a wide range of biological properties. They display moderate antimicrobial effects in a wide variety of preclinical antimicrobial models. Isatin also exhibits other biological activities, such as anticonvulsant, cytotoxic, antifungal etc. Isatin and its analogs are versatile substrates, which can be used for the synthesis of numerous heterocyclic compounds Sridhar & Sreenivasulu, 2001;Sarangapani & Reddy, 1994;Varma et al., 2004;Pandeya et al., 1999;Aboul-Fadl et al., 2010). In our work, we are interested in developing a new 5-bromoisatin and continuing the research work of Qachchachi to explore other applications (Qachchachi et al., 2013(Qachchachi et al., , 2014Kharbach et al., 2016). The present paper reports the synthesis and crystal structure of 5-bromo-1-methylindoline-2,3-dione (see Scheme).The title compound is built up from two fused five-and six-membered rings linked to two ketone O atoms, a Br atom and a methyl group, as shown in Fig. 1. Besides the methyl H atoms, all the atoms of the structure are almost coplanar, with a maximum deviation of À0.1025 (4) Å for the Br1 atom.

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“…Recently, isatin derivatives have attracted strong interest in organic and medicinal chemistry due to their potent biological and pharmacological activities including antitumor (Premanathan et al, 2012;Havrylyuk et al, 2011), antimicrobial (Singh et al, 2010;Ali & Alam, 1994;Pandeya et al, 1999b), anti-inflammatory and analgesic (Abele et al, 2003;Mondal, et al, 2010), antimycobacterial (Aboul-Fadl et al, 2010;Sriram et al, 2006), anticonvulsant (Malawska, 2005), antiviral (Selvam et al, 2006;Selvam et al, 2008;Abbas et al, 2013), anthelmintic (Suresh et al, 2011), anti-HIV applications (Pandeya et al, 1999a) and anti-oxidant (Andreani et al, 2010;Kiran et al 2013). In this context, the present study reports the synthesis and crystal structure determination of the title bis-indole derivative.…”

Section: Structure Descriptionmentioning

confidence: 99%

3-Hydroxy-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-2,3-dihydro-1H-indol-2-one

et al. 2017

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The conformation of the title molecule, C16H12N2O3, is partly determined by an intramolecular C=O...π interaction between one carbonyl group and the five-membered ring of the other indolinone moiety. The crystal packing consists of layers parallel to (001) formed by a combination of N—H...O and O—H...O hydrogen bonds and π–π stacking interactions. Both the N—H...O and O—H...O hydrogen bonds generate inversion dimers.

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Synthesis and antimicrobial activity of Schiff and Mannich bases of isatin and its derivatives with pyrimidine

Cited by 332 publications

References 2 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

5-Bromo-1-methylindoline-2,3-dione

3-Hydroxy-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)-2,3-dihydro-1H-indol-2-one

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