Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents

Panneerselvam, P.; Nair, Rajasree R.; Gudaparthi, Vijayalakshmi; Subramanian, Ekambaram Harihara; Sridhar, S.

doi:10.1016/j.ejmech.2004.09.003

Cited by 293 publications

(135 citation statements)

References 3 publications

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“…Schiff bases are important class of compounds in medicinal and pharmaceutical field. They show biological applications including antibacterial [1][2][3][4][5][6], antifungal [3][4][5][6] and antitumor activity [7,8].…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of N,N'-bis(4-methoxy-benzylidene)hydrazine, C16H16N2O2

Jin¹,

Zhang²,

Zhang³

et al. 2007

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe title compound was prepared by the reaction of hydrazine (0.002 mol) and 4-methoxybenzaldehyde (0.002 mol) in ethanol (10 mL) was treated with concentrated HCl (0.1 mL). The desired product was obtained by filtration, drying and recrystallization from ethanol. Single crystals suitable for X-ray data collection were obtained by slow evaporation of an ethanol solution. DiscussionCompounds with the structure of C=N (azomethine group) are known as Schiff bases, which are usually synthesized from the condensation of primary amines and active carbonyl groups. Schiff bases are important class of compounds in medicinal and pharmaceutical field. They show biological applications including antibacterial [1-6], antifungal [3-6] and antitumor activity [7,8].In the crystal structure of the title compound, the two benzene rings (C2®C7) as well as the other two benzene rings (C10®C15) are essentially coplanar. The bond angles of C16C13C14, C16C13C12, C6C5C8 and C6C5C4 close to 120°as well as the bond lengths of C13C16 (1.461(6) Å) and C5C8 (1.459 (6)

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Section: Discussionmentioning

confidence: 99%

Crystal structure of N,N'-bis(4-methoxy-benzylidene)hydrazine, C16H16N2O2

Jin¹,

Zhang²,

Zhang³

et al. 2007

Zeitschrift Für Kristallographie - New Crystal Structures

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“…Since crystal structures of HDAC3 and HDAC4 in complex with SAHA have not been determined so far, we used the crystal structure of HDAC8 in complex with SAHA which shows sequence similarity (46%) to HDAC4 [1], for docking experiments of compound 5 g , 5 h , and 6 k . We implemented control docking experiments with SAHA to the crystal structure of HDAC8 using AutoDock program [26,27].…”

Section: Molecular Docking Studiesmentioning

confidence: 99%

“…Presently cancer is the second leading cause of medical death in the US, and is anticipated to exceed heart diseases as the leading cause of death in the coming next few years [1]. According to Council of Health Service breast cancer is the most common cancer among Saudis with 15% of whole reported cancer.…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, Molecular Modelling and Biological Evaluation of Novel α-Naphtholhydroxamate Derivatives as Potential Anticancer Agents

Abdelrahim¹,

Mohan²,

Albarrati³

et al. 2016

Med chem (Los Angeles)

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Chemotherapy is one of the treatment options for cancer. A major problem in cancer chemotherapy is the lack of selective toxicity of many commonly used anti-cancer agents towards tumor tissue compared to normal tissue. Studies have shown that α-naphthol is selectively toxic to cultures of human tumor tissue compared to normal tissues in vitro. Hence, this study was conducted to synthesize a series of new hydroxamate derivatives containing α-naphthol nucleus by the reaction of naphthol acetic acid with amino acid methyl ester derivatives which were directly reacted with hydroxyl amine at room temperature. Structures of these compounds were confirmed by standard studies of IR, 1 H NMR, 13 CNMR, MS and elemental analysis. The cytotoxicity of the synthesized compounds were studied using the MTT assay in four human cancer cell lines, including HepG2, PC-3, HT-29 and MCF-7. Among the compounds, compound 6 g and 6 h exhibited a significant cytotoxicity against almost all the used cells including the normal cells . Further studies have shown that the cell death observed was closely associated with generation of reactive oxygen species (ROS). In this study, other naphthol derivatives have shown significant increase in the level of ROS in concentration dependent manner in treated cells. In conclusion, the study has shown that among the synthesized compounds, compounds 6 g , 6 k and 6 h hold the potential for further research. Furthermore, a molecular docking of the tested compounds was carried out to investigate their binding pattern with the prospective target, HDAC (PDB-code: 1T69).

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“…They have made a considerable contribution to biological applications including antibacterial and antifungal diseases [1][2][3] . They can also act as ligands capable of interaction with various metal ions.…”

Section: Introductionmentioning

confidence: 99%

Synthesis andin vitrobiological evaluation of new heterocycles based on the indole moiety

Kandile

Mohamed

Ismaeel

2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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New compounds based on the indole moiety were synthesized via the reaction of indole-3-carbinal 1 with different nucleophiles such as 6-aryl-[4-(2-methoxybenzyl)pyridazin-3-yl] hydrazones 2a-c, benzidine, 3,3 0 -dimethoxybenzidine 4a,b and 2,6-diaminopyridine 6 to afford hydrazine derivatives 3a-c and three different classes of bis-Schiff bases. The structures of the new compounds were elucidated on the basis of their FTIR, 1 H NMR, 13C NMR spectral data, GC/MS and elemental analysis. The antimicrobial activity of the new compounds was evaluated using a broth dilution technique in terms of minimal inhibitory concentration (MIC) against four pathogenic bacteria and two pathogenic fungi strains. Compound 14b showed excellent activity against Escherichia coli and Klebsiella pneumoniae. Some of the prepared compounds were tested for anti-cancer activity against human cell lines HCT116 (colon), MCF7 (breast) and HELA (cervix). From the results of the in vitro assays, compounds 3a,b, and 18a,c presented promising anti-cancer activity.

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Synthesis of Schiff bases of 4-(4-aminophenyl)-morpholine as potential antimicrobial agents

Cited by 293 publications

References 3 publications

Crystal structure of N,N'-bis(4-methoxy-benzylidene)hydrazine, C16H16N2O2

Crystal structure of N,N'-bis(4-methoxy-benzylidene)hydrazine, C16H16N2O2

Design, Synthesis, Molecular Modelling and Biological Evaluation of Novel α-Naphtholhydroxamate Derivatives as Potential Anticancer Agents

Synthesis andin vitrobiological evaluation of new heterocycles based on the indole moiety

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